In the period since Entourage debuted, 20 years ago Thursday, the show’s been discussed as a time capsule full of many different things, most of which the excavators would like to forget: unexamined male chauvinism; pre-recession financial optimism; a Hollywood whose ’90s excesses were continuing to balloon toward a point of obvious untenability; the worst fashion ever captured on film. And so any remembrance of Entourage is colored by the debate over the degree to which it was in on its own joke. But the truth, which was made very plain while crash-rewatching the entire series over the past couple of weeks, is that in almost all instances, the show understands precisely the ways its characters, and their lives, are ridiculous. It’s not satire—not exactly—but rather a durable comedy about the ways beautiful people try to exert agency over a totally arbitrary world.
The show, created by Doug Ellin and executive produced by Mark Wahlberg, on whose career and social circle it is very loosely based, was a product of HBO’s vaunted, arduous development process. The version of Ellin’s pilot that was first pitched to the network was much darker in tone, closer to the show’s seventh season than its first few seasons. And executives weren’t sure how Ellin would work around a very simple, practical challenge: how to cast the lead. If there’s someone out there who looks like a movie star and can act well enough to carry an HBO series, the logic went, why isn’t he a movie star already?
And so for a while, the same note kept coming back: “Less Vince.” (It makes you recall the persistent, maybe apocryphal stories that The West Wing in its initial conception was never meant to depict the president.) But with the casting of Adrian Grenier—specific around the edges but sufficiently blank, a matinee idol with the slightest hint of an edge underneath—they found someone around whom they could hang the newly carefree project. Together with his pale, Napoleonic best friend and manager, Eric “E” Murphy (Kevin Connolly), his older half-brother, a struggling actor named Johnny “Drama” Chase (Kevin Dillon), and Sal “Turtle” Assante (Jerry Ferrara), a do-everything manchild assistant, Vince navigates the beginnings of superstardom a continent away from his and his crew’s beginnings in Queens, presumably because they thought no one wanted to watch a show about people from Boston.
Entourage was prescient about the centrality of superhero movies to 2010s Hollywood, and about the slow ebb of movie star power, from the Cruise-Roberts apex in the ’90s to the significantly compromised version we have today. But it also aired some of Hollywood’s darker open secrets. It’s sort of shocking to see the show’s defiantly obvious Harvey Weinstein stand-in spit across dinner tables and terrorize colleagues; while neither he nor Ari Gold (Jeremy Piven, based on Wahlberg’s real-life superagent, Ari Emanuel) are implicated in sex crimes, the airing of illicit recordings tars the latter’s reputation in a late-series story line that would be mirrored, over and over again, after the public revelation of Weinstein’s crimes in 2017.
But this is not a social drama. Entourage is at its best when Ari, Vince, and E are trying to maneuver Vince in and out of various projects; for its first four seasons, the show takes place almost entirely between periods of filming, when Vince is pacing, scheming, or lazing around waiting for the next gig. For all its heightened absurdity, Entourage gets intuitively the rhythms of Hollywood, where things move unbelievably slowly until hundreds of millions of dollars are shifted around in a single afternoon. It’s like that Lenin quote about decades and weeks if Lenin took all his lunches at Urth Caffé.
In choosing the best episodes of Entourage, we considered a variety of criteria, from the obvious (the sharpness of the script, the tautness of Drama’s pecs on a given day) to smaller, craft concerns, including direction and music supervision. The latter department, run by Scott Vener, is one of Entourage’s signature elements, an often ingenious blend of hip-hop huge and obscure with sly pulls from other genres and eras. Particularly memorable needle drops are listed with each episode.
While Grenier solved the initial problem about casting a credible movie star, Vincent Chase presents another question entirely: Is this guy any good at his job? We see him shimmer on talk shows and in interviews, but that final scene of Queens Boulevard is a little wooden; in Season 5, after Medellin has bombed at Cannes and been rushed straight to DVD in a nearly career-ruining catastrophe, Vince storms into Ari’s office, telling him he’ll do whatever it takes to get back onto the industry’s A-list. Ari expresses enthusiasm—of course, that’s what he’s there for—but can’t give Vince the validation he seeks when he asks whether Ari believes he’s a good actor. “It remains to be seen,” he says. Later that season, when a director fires him from a movie in which Vince plays a doomed firefighter, we’re made to believe that the director was never going to give Vince a fair shake on set. But the acting we see him do is genuinely terrible; “call my wife, TELL HER I LOVE HER” has been rattling around my brain as I try to fall asleep. Whether intentional or not, Vince’s mediocrity underlines the show’s central point: It doesn’t matter; very little of this does.
96. “Dog Day Afternoon”
Season 3, Episode 14
What happens: E tries to shake Vince to have a weekend alone with Sloan (Emmanuelle Chriqui); Drama and Turtle try to pick up women at the dog park; and Ari tries to sign a predatory TV writer.
Stock up: Lloyd (Rex Lee), who slaps and dresses down said writer in the middle of a club.
Stock down: E, who gets the weekend alone in Napa he wanted—with a furious Sloan.
Notable needle drop: There’s sort of a perverse, bar-on-the-floor beauty to Ari hearing “She Works Hard for the Money” on the radio and having the crisis of conscience that inspires him to go rescue Lloyd.
95. “Porn Scenes From an Italian Restaurant”
Season 7, Episode 9
What happens: Ari explodes at Amanda Daniels (Carla Gugino) when they see one another in a restaurant; unbeknownst to him, the recordings of him being verbally abusive to his staff which surfaced in Deadline Hollywood had been leaked by her ex-assistant.
Stock up: Drama, who finally says yes to producing Johnny’s Bananas.
Stock down: This is Ari’s absolute nadir: professionally embarrassed, his biggest client reeling, his marriage nearing its breaking point.
Notable needle drop: Clipse’s “I’m Good,” mirroring Vince’s own professional arc: still on the A-list, but the initial burst of inspiration is quickly running out.
94. “Motherfucker”
Season 8, Episode 5
What happens: Vince becomes enamored of a Vanity Fair reporter, turning what should be a routine interview into an excruciatingly one-sided date; Ari’s wife, Melissa (Perrey Reeves), finally files for divorce.
Stock up: Andrew Dice Clay, whose holdout for more money on Johnny’s Bananas is not only effective, but right on principle, no matter how stupid and stubborn Drama and E find it.
Stock down: E thinks he’s caught in a complex psychosexual drama with Melinda Clarke, his ex-stepmother (only five years older than Kevin Connolly, for what it’s worth), but is in fact being used as a pawn in her feud with Terrance (Malcolm McDowell).
Notable needle drop: Lloyd, Lil Wayne, and Andre 3000’s “Dedication to My Ex” is just the sort of overproduced, glitzy clot of A-list nothing to perfectly encapsulate the show’s final season.
93. “Date Night”
Season 1, Episode 4
What happens: A group date the night of the Head On premiere takes some socially disastrous turns when Turtle decides to invite a crazed fan who’s mailed Vince nude photos.
Stock up: Pixar’s animated squirrel, who wins the weekend box office.
Stock down: Justine Chapin (Leighton Meester), the supposedly chaste pop star who is nearly torn limb from limb by that obsessed fan.
Notable needle drop: Played diegetically, Jay-Z’s verse on Lenny Kravitz’s “Storm” echoes through a club in a manner so 2004 it might as well be wearing Von Dutch.
92. “Bottoms Up”
Season 7, Episode 5
What happens: Vince strikes up a relationship with Sasha Grey; John Stamos goes behind Drama’s back and offers what would have been his role in the Maui pilot to Bob Saget.
Stock up: Mike Tyson, the future star of The Black Brady Bunch.
Stock down: Lizzie Grant (Autumn Reeser) starts poaching clients from Ari, whose attention has drifted from their needs toward management of his company and courting the NFL—and who is the subject of damning voice recordings.
Notable needle drop: You know it’s a 2010 episode when not one but two Steve Aoki songs are featured.
91. “Out With a Bang”
Season 8, Episode 2
What happens: E learns that Sloan is moving to New York; Ari learns that his wife is dating Bobby Flay; Vince gets Billy Walsh (Rhys Coiro) onboard for his Drama-starring TV movie.
Stock up: Andrew Dice Clay, clawing his way back into the industry as Drama’s costar on Johnny’s Bananas.
Stock down: It has to be said: Drama’s fucking shirt, which Turtle says would fit better at “a bisexual paintball tournament.”
Notable needle drop: Rose Royce’s “Love Don’t Live Here Anymore,” a haunting (if perhaps too literal) response to the news of Sloan’s move.
90. “Security Briefs”
Season 6, Episode 9
What happens: The overbearing security guards grate on Vince, Drama, and Turtle as the increasingly suspicious Ashley (Alexis Dziena) does on E.
Stock up: Though the offer is transparently meant to torment Ari, Adam Davies (Jordan Belfi) lures Lloyd away to become an agent.
Stock down: The sex-shop employee who’s nearly hemmed up by Drama after being mistaken for Vince’s stalker.
Notable needle drop: Marvin Gaye’s “Piece of Clay,” the tender song about longing for familial love dropped as Ari stares longingly at Lloyd’s now-empty desk.
89. “Sniff Sniff Gang Bang”
Season 7, Episode 8
What happens: Randall Wallace quits Air-Walker over Vince’s apparent drug use; the network gets excited about Johnny’s Bananas despite Drama’s ambivalence.
Stock up: Turtle begins to secure financing to expand Avion, the tequila company he’s become involved in, this time from Mark Cuban (and his business partner, played by Bob Odenkirk).
Stock down: In therapy, Ari’s wife makes it clear to him that their relationship is in jeopardy (and their therapist deadpans: “Have you ever tried Lexapro?”).
Notable needle drop: Dennis Brown’s “Concrete Castle King,” foreboding as Vince tries to lure Sasha out of a porn shoot and E tries to confront him.
88. “The End”
Season 8, Episode 8
What happens: While Ari tries to win back his wife, Vince, E, and Turtle try to convince a pregnant Sloan to join E in Paris. As finales go, “The End” is too tidy, too trite, and with misplaced stakes: While Vince feels bad about bungling his initial attempt to smooth things over between E and Sloan’s family, the star of the show has nothing to do in its final episode. And was this, at its core, a series about Vince struggling to find his true love—a notion that the Entourage movie dismisses immediately, and offscreen?
Stock up: The opera singers who endeared themselves to Ari’s daughter (Cassidy Lehrman), before accidentally becoming part of a romantic grand gesture—and then becoming the top priority of Lloyd, who takes over Ari’s mantle at the agency—as Ari has quit and moved with his family to Italy...
Stock down: ...until he receives a phone call offering him one of the most powerful jobs in American industry.
Notable needle drop: Led Zeppelin’s “Going to California,” the final song in the series.
87. “Home Sweet Home”
Season 8, Episode 1
What happens: Vince’s return from court-ordered rehab, following his cocaine arrest in “Lose Yourself,” causes everyone to walk on eggshells—except for E, who feels abandoned and resented.
Stock up: Billy Walsh, who—while welcoming in a near-endless string of women corralled from AA, NA, and Sexaholics Anonymous meetings around L.A.—does his best DMX impression.
Stock down: The mansion, burned to the ground by Turtle’s covert joint smoking.
Notable needle drop: Kreayshawn’s “Gucci Gucci,” which tips the episode’s hand toward Vince’s supposed overdose at his welcome-home party being a stunt even before we see him perched, poised, in bed.
86. “The Young and the Stoned”
Season 4, Episode 9
What happens: After his wife reprises her role on The Young and the Restless, Ari loses his cool and threatens the actor who’s supposed to kiss her.
Stock up: It’s E for landing Anna Faris as a management client—despite being convinced, over and over, that they’re having romantic moments. For once, Eric Murphy is perfectly cast.
Stock down: The weed that Drama describes as being extinct—“like the Yangtze river dolphin.”
Notable needle drop: It has to be the pre-critical reappraisal deployment of Soulja Boy’s “Crank Dat.”
85. “Tequila Sunrise”
Season 7, Episode 4
What happens: Drama, hoping to coax John Stamos into being his costar in the Maui pilot, offends the actor by beating him at ping-pong.
Stock up: Despite entering an evident tailspin, Vince is on the precipice of securing a huge franchise with Air-Walker.
Stock down: Turtle is dejected in Mexico, where he learns that Alex (Dania Ramirez) has tried to connect him with a tequila company which hopes to use Vince as its spokesperson.
Notable needle drop: Cam’ron and Juelz Santana’s “Hey Ma,” the warm, Commodores-sampling song that plays diegetically when the guys decide to make an impromptu Vegas trip—nostalgic and, in context, a little melancholy.
84. “Strange Days”
Season 3, Episode 7
What happens: E fixates on the third party from he and Sloan’s threesome while Ari tries to conceal the office space he’s purchased with the settlement money from Terrance.
Stock up: Adam Davies, who blackmails Ari into a partnership in his new agency.
Stock down: Vince, purchased (as he says) “like an iPod” at a charity auction.
Notable needle drop: The J. Geils Band’s exultant “Give It to Me.”
83. “Fore!”
Season 6, Episode 5
What happens: A celebrity golf benefit stretches the show into the world of mundane entertainment industry do-nothingness outside of the Chase home.
Stock up: Though he lashes out at Sloan for having the audacity to engineer it, E receives a job offer from legendary talent manager Murray Berenson (George Segal).
Stock down: Tom Brady, forced to buy a new driver after Drama snaps it in half following another in a long line of terrible shots.
Notable needle drop: Cam’ron’s Police-sampling “What Means the World to You.”
82. “The Big Bang”
Season 8, Episode 6
What happens: The Vanity Fair article paints Vince as an incorrigible womanizer, causing him to seek out the writer in person.
Stock up: Drama and Dice win their standoff over Johnny’s Bananas salary.
Stock down: Barbara Miller (Beverly D’Angelo), whose control over the agency is threatened by Ari’s divorce.
Notable needle drop: Cannonball Adderley and Bill Evans’s “Know What I Mean?,” an ideal counterpoint to the Diplo and Dillon Francis that plays earlier in the episode.
81. “Dramedy”
Season 7, Episode 3
What happens: With his holding deal running out, Drama meets with a veteran TV writer (Jeff Garlin) who offers him a script about two brothers who work at the Four Seasons Maui.
Stock up: When Ari decides to call Lizzie’s bluff about quitting if she isn’t made head of the TV department, she follows through—sending the agency into a panic.
Stock down: The paleontological community, which is down one $250,000 dinosaur skull, crushed during a party at Vince’s.
Notable needle drop: Diddy–Dirty Money’s “Last Night Part 2,” because when you talk about John Stamos in the 21st century, you need to hear something antic and commercial but a little bit off.
80. “Berried Alive”
Season 6, Episode 10
What happens: While a network executive whom Drama suspects of propositioning Jamie-Lynn Sigler continues to torment him on Five Towns, Drama learns he may have a shot at a Melrose Place reboot. Meanwhile, Ashley demands to read E’s emails.
Stock up: After Ari beats Lloyd in a race to get him out of his Five Towns contract, Drama has the presence of mind to demand the superagent be honest about whether he finds him talented, and is invested in his career, and ultimately turns down the big name for the person who will prioritize him.
Stock down: Jamie-Lynn Sigler, who suffers the greatest indignity of all: being made to feel insecure by UCLA students.
Notable needle drop: One of the most chilling drops in the entire series: Michael Jackson’s “I Wanna Be Where You Are,” which rings out as soon as Jamie-Lynn tells Turtle she’s been offered a series that shoots in New Zealand.
79. “One Last Shot”
Season 8, Episode 3
What happens: Carl Ertz (Kim Coates), the producer who once duped Vince into being a negotiation smokescreen, offers to make good by producing the trapped-miners TV movie—only to relapse and shoot himself in the head while Vince and Turtle are at his home.
Stock up: When Ari arrives at Dana Gordon’s (Constance Zimmer) house late at night, he’s not only reclaiming a bit of the self-worth he’s lost during his separation, but acting on a bit of long-obvious chemistry.
Stock down: Turtle is dumped by Alex and told his services are no longer needed at Avion.
Notable needle drop: Muddy Waters’s “She Moves Me”
78. “Gary’s Desk”
Season 4, Episode 8
What happens: Hoping to earn himself some name recognition and legitimacy, E sits for an interview with Variety, which is spun into a piece about the “new nepotism” in Hollywood.
Stock up: E’s gambit does in fact pay off when a very patient Peter Jackson calls, grateful that those who want to work with Vince can work around Ari.
Stock down: The identical twin agents in Ari’s office (the Sklar Brothers): the one who sleeps with the other’s wife is retained (though humiliated) because he outearns his brother, who is fired despite being a favorite of guest star Mary J. Blige.
Notable needle drop: While the Geto Boys’ “Damn It Feels Good to Be a Gangsta” strikes a perfect tonal note to open the episode, the best pull is El-P’s “EMG.”
77. “Less Than 30”
Season 3, Episode 13
What happens: The premiere of “Season 3 Part 2,” a relic of the writers’ strike. On the eve of Vince’s birthday, Amanda pushes an Edith Wharton adaptation despite Vince and E’s ambivalence—which only grows stronger when Ari suggests Medellin might once again be within their grasp.
Stock up: SKYY Vodka, its bottle placed conspicuously in all birthday party photos by Turtle, who turned the wildly over-budget affair into a garishly sponsored revenue stream
Stock down: Amanda, already: her biggest client is chasing the ghost of a project dangled by his former agent.
Notable needle drop: Brand Nubian’s “Slow Down” during the first walk through Amanda’s office
76. “No More Drama”
Season 6, Episode 7
What happens: An evident break-in at Vince’s house inspires him and the others to consider various security options, including some firearms no one in this crew is qualified to carry.
Stock up: Though it’s just his first day at his new job, E correctly senses that a bizarre request from Bob Saget is worth passing up to Murray.
Stock down: Drama confronts the executive who said vile things about Jamie-Lynn, but loses his cool and gets physical; the executive promises to torture Drama for the duration of his Five Towns contract.
Notable needle drop: “Straight Outta Compton,” playing over the end credits after the gun purchased to protect against an apparent stalker accidentally shoots out a window.
75. “The Prince’s Bride”
Season 3, Episode 19
What happens: After spending $5 million of their own money to buy the Medellin script, Vince and E try to secure financing from a foreign couple with some odd conditions.
Stock up: Sylvester Stallone, apparently: The financiers insist that having him play Pablo Escobar would guarantee that the movie would open overseas.
Stock down: The sea otter who was pelted by a sno-cone, ruining Turtle’s first date.
Notable needle drop: B.B. King’s “Why I Sing the Blues” is pretty appropriate after a man who you’ve just been told “might be Mossad, might be Hezbollah” demands you walk upstairs and fuck his wife.
74. “First Class Jerk”
Season 5, Episode 8
What happens: Ari receives a formal offer of $10 million for the studio job and learns that if he passes, it will go to Amanda—again closing off Warner to Vince and the rest of Ari’s clients.
Stock up: Dana Gordon, who Ari successfully maneuvers into the job when he passes.
Stock down: After sharing a romantic moment with Jamie-Lynn—which Drama especially assumes was a lie—on a flight back from Hawaii, Turtle gets a drink thrown in his face in the middle of a crowded bar.
Notable needle drop: The absolutely insane pull of Basic Vocab’s “Come Get With It” over the closing credits.
73. “The Day Fuckers”
Season 4, Episode 7
What happens: While Turtle and E compete to see who can have “unemotional sex” the soonest, Ari goes to extreme lengths to get his son into the school of his choice.
Stock up: For a show that is so often characterized, even caricatured, as a fantasy of crude masculinity, Entourage takes plenty of opportunities to arrive at tidy moral lessons, as if it aired on CBS in prime time in the early ’80s. Ari is ultimately able to sway the headmaster, not through blackmail or subterfuge, but through honesty and humility.
Stock down: All of us watching when Ari’s son asks his dad whether he’ll get to go to school with his best friend.
Notable needle drop: The Pinker Tones’ “Sonido Total”; imagine playing this for the boys back in Queens before Head On.
72. “Unlike a Virgin”
Season 5, Episode 2
What happens: Feeling rejected by the industry, Vince has his version of a breakdown in front of Ari—who, while he expresses enthusiasm about Vince’s return to movie stardom, admits that it “remains to be seen” whether he’s a good actor.
Stock up: The wonderfully cast gun-toting writing duo (Lukas Haas and Giovanni Ribisi) who sign with E after getting him their script about nine firefighters.
Stock down: Drama, who’s dumped by his long-distance girlfriend because of his extreme possessiveness.
Notable needle drop: Anytime you can get Tony Bennett to turn up and sing “The Good Life,” you do it.
71. “Buzzed”
Season 7, Episode 2
What happens: When he’s prescribed painkillers after the driving stunt goes haywire, Vince starts to crack: He cuts his hair without consulting Nick Cassavetes about reshoots and quips during a press junket that the movie might “suck.”
Stock up: Ari is told by Jerry Jones that his fellow NFL owners want Ari to bring a team to L.A. (although you wonder if, had Entourage been given a ninth season, there would have been a B plot about chartering Sprinter vans to ferry celebrities to a makeshift stadium in Carson).
Stock down: Already annoyed—and made paranoid—by a fellow manager at his firm, Scott Lavin (Scott Caan), E is further marginalized when he finds out that Scott’s taken Vince skydiving.
Notable needle drop: When you’re asked to cite songs that serve as markers of time, the instinct is to look at the pop charts. But tracks like Skyzoo’s “Popularity” are perhaps even more frozen in amber.
70. “Lose Yourself”
Season 7, Episode 10
What happens: An intervention for Vince goes about as poorly as possible, as he lashes out at his closest friends and seems to head directly—and knowingly—into oblivion.
Stock up: Nothing goes particularly well for any of our principal characters, but at least Terrance’s demand that E sign a prenup sets into motion Scott’s plan to take over Murray’s management company.
Stock down: Ari, whose wife leaves him and goes to her sister’s house while he’s planning her a grand surprise party.
Notable needle drop: At the party Eminem’s throwing in the hotel where Vince goes to hole up, drink, and do coke, his shticky “W.T.P.” is made to echo around in negative space just enough to pass as a legitimate club song.
69. “Second to Last”
Season 8, Episode 7
What happens: Vince embarks on the utterly bizarre project of interviewing his exes to prove that he’s a good guy.
Stock up: Turtle’s attempt to coax the owners of Don Pepe’s into an L.A. expansion proves to be a wild goose chase—but he comes into some unexpected money when Vince reveals that he never sold their Avion stock.
Stock down: E learns that Sloan is pregnant with his child but is moving to New York.
Notable needle drop: Billy Squier’s “My Kind of Lover” pumps tinnily out of Turtle’s Macbook.
68. “Fantasy Island”
Season 5, Episode 1
What happens: Six months after Medellin was booed out of Cannes and straight to DVD, Vince and Turtle are holed up on a remote Mexican beach when a movie role that could serve as a much-needed comeback seems to become available.
Stock up: While still reeling from that disastrous career move, E is clawing together a management roster besides Vince, including Charlie (Bow Wow), a young comic looking to land a pilot deal.
Stock down: Ari, who doesn’t realize that the meeting he’s lured Vince back to L.A. for—a producer is ostensibly offering him a role in a genre thriller—is simply meant to close another actor’s deal.
Notable needle drop: “Return of the Mack” soundtracks the seaplane that Ari and E have chartered to go find Vince.
67. “The Script and the Sherpa”
Season 1, Episode 5
What happens: In the midst of a county-wide weed drought, Vince’s new hippie girlfriend tests the crew’s patience, while Vince tests Ari’s by expressing a desire to do an indie movie.
Stock up: Ari’s ex-assistant Josh Weinstein (Joshua LeBar), who gets the script for Queens Boulevard to Vince and E.
Stock down: Turtle, who can’t work any of his usual plugs (and suddenly knows a lot about drought ecology).
Notable needle drop: Ol’ Dirty Bastard’s “Got Your Money,” pumping through Gold’s Gym.
66. “Gotta Look Up to Get Down”
Season 5, Episode 7
What happens: While Vince is flummoxed by his costar’s firing from a Dolce & Gabbana campaign, Ari is offered Alan Gray’s (Paul Ben-Victor) vacated studio job.
Stock up: Ari, who has the option to become one of the most powerful people in the entire entertainment business.
Stock down: Also Ari, who for the moment has to patiently explain to Jeffrey Tambor why audiences might not buy him as Marcel Proust.
Notable needle drop: A Tribe Called Quest’s slinking “Check the Rhime,” which soundtracks Vince’s financially inadvisable stand on principle.
65. “The Review”
Season 1, Episode 2
What happens: Vince is eviscerated in Variety for his performance in Head On—then, in the episode’s last scene, lavished with praise in The New York Times.
Stock up: Vince’s business manager Marvin (Paul Herman), who doubts the medical feasibility of Drama’s vitamin intake, screams about Turtle’s cellphone bill, and reminds E to get his parking validated.
Stock down: Leighton Meester, who debuts her thankless character: a pop star marketing her virginity.
Notable needle drop: The devilishly ironic use of “Work” by Gang Starr over the closing credits.
64. “Seth Green Day”
Season 5, Episode 10
What happens: Smoke Jumpers production continues to be a disaster for Vince, as it becomes clear that director Verner Vollstedt (Stellan Skarsgard) has little interest or faith in him.
Stock up: Charlie, who teams up with E to once again beat up Seth Green, this time in a network boardroom.
Stock down: Andrew again, who has a panic attack when Barbara interrogates him about whether he’d be a fit at Miller Gold.
Notable needle drop: It’s sort of hard to explain to anyone who wasn’t there how big Kid Cudi’s “Day ’n’ Nite” felt at the time.
63. “No Cannes Do”
Season 4, Episode 11
What happens: A security threat closes down LAX as the Medellin team prepares to leave for France.
Stock up: Ari’s wife, who spends an exorbitant amount of money—including on a Maybach—because he’s going to Cannes without her.
Stock down: Lloyd, who is told he can make the trip, then turned away when Sydney Pollack’s jet doesn’t have enough open seats.
Notable needle drop: Kanye West, one of the worst actors to ever grace HBO, uses the final scene of the episode to premiere “Good Life,” which here features an extended intro.
62. “Tequila and Coke”
Season 7, Episode 7
What happens: Vince’s behavior in Air-Walker meetings grows even more troublesome as his cocaine use escalates.
Stock up: Avión tequila, which, despite conflict between the founders and Turtle over control of the brand in the States, becomes a commodity in Hollywood.
Stock down: Even though he made amends with Lizzie, tapes of Ari berating employees are leaked to Deadline Hollywood, ending his relationship with the NFL and throwing his work and family lives into chaos.
Notable needle drop: Masta Killa, RZA, and ODB’s “Old Man,” although KMD’s “Stop Smoking That Shit” is a phenomenal pull as well.
61. “Drive”
Season 6, Episode 1
What happens: With Martin Scorsese’s Gatsby set to premiere (and Frank Darabont’s Enzo Ferrari biopic ready to shoot), Vince has added critical acclaim to his Aquaman-era box office appeal.
Stock up: Nearly everyone: In addition to Vince’s career upturn, Turtle is happy with new girlfriend Jamie-Lynn, Drama is thriving on Five Towns, and E seems to be on the road to reconciling with Sloan.
Stock down: Andrew Klein (Gary Cole), whose wandering eye is made uncomfortably apparent.
Notable needle drop: The episode ends with an uncharacteristically schmaltzy trick typical of season premieres: a montage, set to the Verve’s “Lucky Man,” meant to illustrate how every character’s life is trending upward—but how that change is a little bit melancholy, too.
60. “Entourage”
Season 1, Episode 1
What happens: The week of the Head On premiere, Vince and E draw Ari’s ire after passing on a $4 million offer to do a poorly written action movie called Matterhorn. As pilots go, “Entourage” does strike a unique tonal balance, casting the four friends as fish who are at least slightly out of water in wealthy L.A., but who have deeply worn grooves in their friendships. There’s little suggestion of the angst or tragedy that will come, but as sheer wish fulfillment, it’s difficult to beat.
Stock up: Arnold, the guard dog who arrives and immediately establishes himself as the alpha in the house.
Stock down: Nearly everyone: Ari for being overruled by a naive client and his inexperienced manager, and Vince and E when Colin Farrell takes the Matterhorn gig.
Notable needle drop: With respect to the era hyper-specificity of Joe Budden’s “Fire,” it’s Jay-Z’s “Lucifer,” which hangs ominously over the closing credits.
59. “Malibooty”
Season 4, Episode 3
What happens: Pessimistic about the film’s quality and commercial prospects, E secures an offer from Harvey Weingard (Maury Chaykin) to buy Medellin for less than its initial budget.
Stock up: Medellin itself after it’s accepted into Cannes, shocking E.
Stock down: After begging Turtle to play wingman so that he might have a chance to sleep with a socialite (Lisa Rinna) he’s had a crush on for decades, Drama is stunned into silence when the girls decide to switch partners.
Notable needle drop: The Chronic’s “Lil’ Ghetto Boy,” a masterpiece that makes terror feel a little wistful.
58. “Murphy’s Lie”
Season 6, Episode 6
What happens: While filming their Five Towns scene, Drama grows paranoid that an NBC executive is trying to sleep with Jamie-Lynn.
Stock up: After days on the couch following the revelation of Andrew’s affair, Ari inches his way back into his wife’s good graces.
Stock down: All other relationships: Ashley and E’s breakup is sedate compared with Andrew’s situation with his wife, who storms into Miller Gold, screaming at every woman she sees.
Notable needle drop: The Dutchess & the Duke’s “Reservoir Park.”
57. “Stunted”
Season 7, Episode 1
What happens: Cassavetes pressures Vince into performing a dangerous stunt—jumping a speeding car off a ramp and toward a burning building—without clearing it with the studio or insurance company.
Stock up: Apparently Dean Cain, who gets cast in a remake of The Fall Guy—at Drama’s expense.
Stock down: Turtle tries to make out with his employee Alex after she breaks down about her parents’ divorce; it’s played as a sitcom misunderstanding, but it’s one of a handful of incidents that, if the show aired 10 years later, might be cast in a far more sinister light.
Notable needle drop: Gang Starr’s Inspectah Deck–featuring “Above the Clouds”; while the Vince character is named after Vince Vaughn and has personal or professional elements of Wahlberg, Tobey Maguire, and others, a little Leo sneaks in with every Gang Starr drop.
56. “Hair”
Season 7, Episode 6
What happens: Ari’s agency prepares for litigation, scandal, or both.
Stock up: Billy Walsh, who returns—square as a prison meal, in Gap, and refusing to curse—and almost immediately has a brilliant idea for Drama’s TV show.
Stock down: The malaise and substance abuse that were already apparent to the guys bleed into Vince’s professional life when the director and studio executives behind Air-Walker become concerned about his behavior in meetings; the episode’s final shot shows him passed out on the ledge of his pool.
Notable needle drop: Sister Nancy’s “Ain’t No Stopping Nancy.”
55. “Talk Show”
Season 1, Episode 3
What happens: Drama urges Vince to blow off Jimmy Kimmel’s show because of a perceived slight from years ago.
Stock up: Luke Wilson, who talks about Rufus’s (Marlon Young’s) home entertainment system like he’s in Death of a Salesman.
Stock down: Shauna (Debi Mazar), Vince’s razor-tongued publicist, who is powerless in the face of an ambivalent client and free surround-sound system.
Notable needle drop: LL Cool J’s “Headsprung”—the perfect soundtrack to the Kimmel greenroom, which Drama says is “stocked like a trout pond.”
54. “Aquamansion”
Season 2, Episode 3
What happens: Vince does what so many actors have done before: He agrees to take a job so that he can buy a bigger house, in this case Marlon Brando’s.
Stock up: Drama, who successfully overcomes a years-old banishment from the Playboy Mansion.
Stock down: Hollywood. Hearing Dana Gordon promise that Aquaman will be “a darker, grittier film” is excruciating.
Notable needle drop: “Stayin’ Alive” by the Bee Gees as the introduction to the mansion—sometimes clichés are clichés for a reason.
53. “Amongst Friends”
Season 6, Episode 2
What happens: Ari’s and Andrew’s wives become fast friends—causing tremendous anxiety for Ari, who has learned about Andrew’s affair with Lizzie.
Stock up: Martin Scorsese, whose Gatsby apparently did what Baz Luhrmann’s real-world version could not and garnered universal acclaim.
Stock down: Seth Rogen, whose alleged lack of sex appeal is an episode-long fixation of Turtle’s.
Notable needle drop: Erick Sermon’s “Music,” because when Sermon raps, you can always tell there’s something nagging at him just beneath the surface.
52. “Adios, Amigos”
Season 3, Episode 20
What happens: With Vince and E’s money tied up in the Medellin script—as they pursue Billy Walsh to direct the movie—the boys sell the house and scramble for new living situations.
Stock up: Brian Palermo’s effete real estate agent, who barely has to blink to drive Drama hundreds of thousands of dollars over asking price on a condo.
Stock down: The porn company that had contracted Walsh (under the name Wally Balls) to a 25-picture deal to “bring the 1970s-type class back to porn—and the wide bush.”
Notable needle drop: Clyde Carson’s “2 Step,” another relic from the mid-2000s sprawl of Aftermath-adjacent rappers with hyper-clean, piano-led beats and heavy low ends descended directly from 2001.
51. “New York”
Season 1, Episode 8
What happens: Turtle plots a going-away party before the Queens Boulevard shoot; Vince and E’s working relationship grows untenable.
Stock up: Drama, who, after his post–Viking Quest dry spell, has to choose between his role in Queen Boulevard and the pilot for CSI: Minneapolis.
Stock down: Ari, after Larry David catches him at a Lakers game with Vin Diesel.
Notable needle drop: James Gang’s “Funk #49,” a false note of optimism to close the first season.
50. “The All Out Fall Out”
Season 5, Episode 3
What happens: E learns from Amanda that Ed Norton is interested in his writers’ script, while Vince takes a $200,000 appearance fee to sing Frankie Valli at a sweet 16 party.
Stock up: While there are plenty of outstanding celebrity cameos in Entourage, few reach the heights that T.I. does here when he tells Ari he wants to star in Black Sabbath, a movie about a Black man who has an affair with an older Jewish woman. He’s thinking Meryl Streep.
Stock down: Adam Davies, who gets slapped in front of his colleagues after crossing a line during a prank war with Ari.
Notable needle drop: We need a truth and reconciliation committee for those who wrote Charles Hamilton’s “Brooklyn Girls” out of history.
49. “My Maserati Does 185”
Season 2, Episode 2
What happens: Turtle, Drama, and Vince are proved right—E’s girlfriend is cheating on him.
Stock up: Ari, who marches into a sauna in a wool suit and Windsor knot to read the opening scene of the Aquaman script.
Stock down: Drama, who can’t stop asking anyone—up to and including Lamar Odom—about their calves.
Notable needle drop: Akon’s Melle Mel riff “Show Out.”
48. “The Cannes Kids”
Season 4, Episode 12
What happens: Just before the Cannes premiere of Medellin, Ari and the boys decide to accept a $28 million offer for the movie from Dana—only to find out that Nicky Rubenstein (Adam Goldberg) has already accepted $75 million from a foreign buyer with no distribution or awards acumen.
Stock up: Harvey, who, after the movie is roundly booed during its disastrous premiere—which causes the foreign buyer to back out, insisting he never signed any papers—is able to purchase Medellin for a single dollar.
Stock down: Nicky, who stalks around his property wearing an ankle monitor, barking that the beautiful sex workers he’s hired are “enablers.”
Notable needle drop: Citizen Cope’s “Let the Drummer Kick” is an appropriate but still pretty comical soundtrack to an aging fantasy show star’s search for the girl half his age who’s seen his whole series with subtitles.
47. “An Offer Refused”
Season 2, Episode 4
What happens: Vince et al. start decorating the house they can’t afford—and the Aquaman offer is nowhere to be found.
Stock up: Chris Penn, who—on top of stiffing Drama on the payment for painting his house—absolutely demolishes him in the boxing ring.
Stock down: Ari, who can’t get James Cameron or Dana on the phone.
Notable needle drop: Jeezy’s “And Then What,” played diegetically during Penn’s pummeling of Drama, or Foxy Brown’s “I’ll Be,” from the rug pull of a closing scene
46. “The Resurrection”
Season 3, Episode 18
What happens: Ari finds a producer who will finance Medellin, but only if Vince agrees to make Matterhorn first.
Stock up: All of Five Towns—a massive hit on its debut despite the slew of viciously negative reviews.
Stock down: The guys, who have to wait for Drama to make breakfast: one day because his premiere nerves made him oversleep, the next because he drove himself to the Grand Canyon out of despair.
Notable needle drop: “Elevation (Free My Mind)” by the B.U.M.s, the underappreciated duo from Oakland.
45. “One Car, Two Car, Red Car, Blue Car”
Season 6, Episode 3
What happens: On Turtle’s 30th birthday, he receives not one but two luxury cars, which contributes to a growing complex about his lack of direction in life—one he staves off by enrolling in business classes.
Stock up: Ari, who is positively delighted to hear that E called a network executive a racist, following his half-joking advice.
Stock down: Poor Charlie, who is recast in his own sitcom because he tested poorly in focus group screenings.
Notable needle drop: 50 Cent’s “OK, You’re Right,” which plays as 50 laughs at Turtle in the now famous GIF.
44. “Blue Balls Lagoon”
Season 2, Episode 11
What happens: Ari makes a show of giving Vince an expensive painting, which Vince in turn plans to gift to Mandy Moore for her birthday, only for Sloan to reveal that it—like his wife’s Benz 600—is a fake.
Stock up: E, who’s making inroads with both Sloan and Terrance.
Stock down: Shauna is so out of the loop on Vince’s life that she’s unable to keep news of his relationship with Mandy out of Page Six.
Notable needle drop: “I Changed My Mind” by Quannum Projects, a real turn-of-the-century indie rap pull.
43. “Neighbors”
Season 2, Episode 5
What happens: Ari continues to chase the Aquaman offer while rumors swirl that Leonardo DiCaprio is in talks to star, jeopardizing both Vince’s career and his financial situation.
Stock up: Bob Saget, who survives a divorce with four houses and a private jet full of Colombian weed.
Stock down: E, who inadvertently fucks up the Aquaman process by promising James Cameron a print of Queens Boulevard he can’t deliver.
Notable needle drop: Jay-Z and UGK’s “Big Pimpin’” when the guys pull up to what is, unbeknownst to them, a brothel in their neighborhood.
42. “Runnin’ on E”
Season 6, Episode 4
What happens: While Vince’s Ferrari biopic is delayed and Drama’s career hums along, E grows professionally restless—and romantically comfortable with Ashley.
Stock up: After Ed Burns scoffs at the notion that his character’s love interest could be a major actress, Drama is ecstatic to learn that Turtle has convinced Jamie-Lynn to take the guest part on Five Towns.
Stock down: Andrew, who melts down after ending his affair with Lizzie—then crashes her lunch with David Schwimmer.
Notable needle drop: Special Ed’s “I Got It Made.” The show milks New York less than viewers might have initially expected it to, treating the city mostly as a refuge the Chases use to lick their wounds. But there’s something nearly touching when it pulls the songs that Turtle in particular would have realistically listened to in his adolescence there.
41. “Aquamom”
Season 3, Episode 1
What happens: Vince hatches a plan to get his travel-averse mother to attend the Aquaman premiere.
Stock up: Even if he fails to claw back the premiere tickets Turtle and Drama swiped from him, James Woods plays himself in one of the most truly unhinged guest star tours de force in television history: He tramples up an overheated stairwell with the much-younger girlfriend he can’t stand, glowers in security camera live feeds, and grabs Drama by the neck in the middle of a red carpet.
Stock down: In the episode’s B plot, Ari endures a (mostly) deserved string of insults from his wife, who’s been forced once again to cover the new agency’s expenses.
Notable needle drop: Joe Cocker’s “Feelin’ Alright,” because sometimes there’s no point in overthinking it.
40. “The Bat Mitzvah”
Season 2, Episode 10
What happens: James Cameron overhears Vince and Mandy talking about their personal history; moments later, E overhears Vince admitting that he’s never gotten over Mandy. Meanwhile, Ari’s boss Terrance takes an interest in Vince, while E takes an interest in Terrance’s daughter, Sloan.
Stock up: Literally, Ari’s daughter, Sarah, who cashes a $50,000 check from Terrance in addition to all her other gifts.
Stock down: Turtle and Drama, who are banished to the far reaches of table 19.
Notable needle drop: Tony Yayo’s “So Seductive,” dropped—inexcusably—by special guest DJ Quik during a bat mitzvah.
39. “Return to Queens Blvd.”
Season 5, Episode 12
What happens: As they lick their wounds in their parents’ houses (and in an array of late-night party spots), Vince’s frustration finally boils over, and he fires E.
Stock up: By episode’s end, it’s E: His seemingly quixotic plan to get Gus Van Sant to see dailies from Smoke Jumpers indirectly leads to Vince’s casting as the lead in Martin Scorsese’s Great Gatsby adaptation.
Stock down: Turtle, whose landline phone sex with Jamie-Lynn is interrupted by his mother.
Notable needle drop: De La Soul’s “Me Myself and I,” which plays during a cheery trip to the club, pretty fitting for a handful of vacationing 30-or-sos from Queens.
38. “Welcome to the Jungle”
Season 4, Episode 1
What happens: Vince, E, and Billy Walsh attempt to shoot Medellin in Bogotá, Colombia, as Billy becomes fixated on an actress, clashes with Vince over his performance (and said actress), and refuses to show anyone dailies.
Stock up: Stephen Gaghan, the celebrated screenwriter who gets paid $275,000 to rewrite the Medellin ending, only to step off the plane and find out there’s nothing for him to do.
Stock down: The wonderfully nervy financier Nicky Rubenstein, who was arrested with cocaine en route to the airport before shooting, is locked in a rehab facility, and can’t stop worrying that his money is being lit on fire. “There’s no suicide watch here, you know what I mean?”
Notable needle drop: Except for brief cutaways to Los Angeles, there’s no pop music in this format-breaking, Hearts of Darkness–style mockumentary episode.
37. “Gotcha!”
Season 3, Episode 16
What happens: Drama is the victim of Pauly Shore’s Inception-deep hidden camera show.
Stock up: Ari’s old college buddy (Artie Lange), who “made a fortune in stamps.”
Stock down: His buddy’s fiancée (Leslie Bibb), who becomes the object of Ari’s faux affection.
Notable needle drop: Elvis Costello’s “(I Don’t Want to Go to) Chelsea,” as self-involved as Vince and Amanda.
36. “I Love You Too”
Season 2, Episode 9
What happens: At Comic-Con in San Diego, Vince’s personal life continues to jeopardize Aquaman—this time because he blows up an interview with an influential blogger who presses him about Mandy.
Stock up: Drama, who is the marquee Chase brother for a weekend, his Viking Quest booth a perennial favorite for the acned masses.
Stock down: A flailing Vince, who leans on Shauna to find him a date for the dinner with Mandy and her fiancé, which he eventually blows off out of fear.
Notable needle drop: “Rock the Casbah” as the introduction to Comic-Con’s den of arcanity.
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35. “Chinatown”
Season 2, Episode 6
What happens: With Aquaman still in limbo, Vince books a $500,000 payday shooting a commercial for a Chinese energy drink.
Stock up: Scott Wick (Stanley DeSantis), the Queens Boulevard producer who dials E’s gay panic up to 11.
Stock down: The agent who pitches a TV show for Vince and is kicked out of Ari’s conference room without even a bagel for her troubles.
Notable needle drop: The Freestylers’ “Right On,” pulsing during a video game tournament.
34. “Give a Little Bit”
Season 6, Episode 12
What happens: Ari becomes head of the largest entertainment agency in the world, E proposes to Sloan, and Drama sings for his supper.
Stock up: The speech Drama gives at his retest for Melrose 2009 is genuinely tragic and shows a self-awareness that no other character expresses at any point in Entourage. (Special mention to Matt Damon’s post-credits tag.)
Stock down: Adam Davies, the chief victim in Ari’s paintball rampage as downsizing.
Notable needle drop: Jay-Z’s “In My Lifetime” over the season-ending sequence.
33. “The Sorkin Notes”
Season 6, Episode 8
What happens: After Andrew is caught sleeping on the couch in Ari’s office, Barbara offers an ultimatum: He signs Aaron Sorkin by the end of the day, or he’s fired.
Stock up: Somehow, Andrew, who convinces Sorkin to sign with Miller Gold—from jail after his arrest for driving a car into his own house.
Stock down: Sloan, after E has an abrupt (and inadvisable) change of heart and bails on drinks with her in favor of Ashley.
Notable needle drop: Nelly’s “E.I.,” if only because E’s pivot from Sloan to Ashley is so sickeningly literalized by Nelly’s line about “drafting ’em outta high school straight into the pros.”
32. “The First Cut Is the Deepest”
Season 4, Episode 2
What happens: Ari learns that his son’s admittance to an elite private school is in jeopardy; Billy flees when he has second thoughts about showing Vince and E a cut of Medellin.
Stock up: Billy is allowed to live in brief, blissful ignorance when Vince and E tell him they love the cut; little does he know, E finds it so flawed that he’ll soon try to sell the rights to someone who can force Billy off the project.
Stock down: The endangered sea bass Billy has flown in to the postproduction offices every Thursday.
Notable needle drop: Wale’s too-clean “Ice Cream Girl” at the party that Drama so painstakingly tries to make sterile by removing all furniture from his apartment and padlocking the bathroom.
31. “The Release”
Season 3, Episode 8
What happens: The other major agencies mobilize against Ari; Vince and Billy Walsh sign an injunction against the release of a studio-butchered version of Queens Boulevard.
Stock up: Judging by the near castle where he’s house-sitting, the ginseng company owned by the parents of Billy’s girlfriend.
Stock down: Ari, suddenly broke again.
Notable needle drop: Entourage was in production just as the CD sales economy that propped up the music industry was collapsing. Here, Lloyd Banks’s “My House” stands as a last vestige of when those merely adjacent-to-A-list rappers could command massive budgets. It’s also a real-world parallel to Saigon’s fictional plot to steal an Interscope executive’s car to plant his demo: “My House” was set to be on the second Lloyd Banks LP, which was scrapped when a rough cut was lifted from a valeted car and leaked online.
30. “Snow Job”
Season 4, Episode 10
What happens: While E is out of reach tending to his new management client, Ari, Dana Gordon, et al. scramble after Billy Walsh turns in a script that’s totally divorced from the book he was paid to adapt.
Stock up: While it’s Ari who has the audacity to break into a studio head’s office, Dana’s on-the-spot pitch (“Blade Runner meets Field of Dreams”) sells Silo.
Stock down: Technically, Billy is totally without power—but it’s still exhilarating to hear him respond to Ari’s insistence that he’ll never be allowed to make a movie again with “Good thing I paint.”
Notable needle drop: Pharoahe Monch’s “Body Baby,” which is a little more dignified than you remember.
29. “Good Morning Saigon”
Season 2, Episode 12
What happens: The guys pick up their stolen Maserati only to find a rapper’s demo in the CD deck; Mandy’s team tries to put the fear of god in E.
Stock up: Turtle not only successfully convinces Billy Walsh to put one of Saigon’s songs in Queens Boulevard, but also bluffs his way into his first management client.
Stock down: Vince, whose decision to blow off a meeting by staying in bed with Mandy puts his Aquaman role in jeopardy.
Notable needle drop: We catch clips of a few different Saigon songs, but none stick like “Let a N---- Know.”
28. “Fire Sale”
Season 5, Episode 4
What happens: Ari, E, and Vince take the firefighter script, now titled Smoke Jumpers, from studio to studio, looking for a deal.
Stock up: Whoopi Goldberg, who interrogates Drama about his breakup on The View as if she’s never heard any of the words he uses to describe it before.
Stock down: While E’s writers are unknowns, it quickly becomes clear that the biggest obstacle to a sale is Vince, who quickly suggests that he be bumped down to a supporting role—a concession that matters very little when Warner steps in to make an offer E can’t refuse.
Notable needle drop: Naughty by Nature’s “Feel Me Flow,” because few songs would be more obvious, instant markers of celebration for these guys.
27. “The WeHo Ho”
Season 4, Episode 6
What happens: Despite the tension between E and Billy Walsh, Vince agrees to star in the Walsh-directed mountain climber movie Lost in the Clouds.
Stock up: Sandy Koufax, who is apparently in perfect health—despite suggestions otherwise from Turtle’s cousin Ronnie (Louis Lombardi), who ropes Turtle and Drama into investing in a game jersey on the assumption that the legendary pitcher is on death’s door.
Stock down: While it’s Lloyd who’s confined to bed during his temporary breakup with Tom (Brandon Quinn), it’s hard to argue with the pain in the latter’s voice when he tells Ari’s that he’s on “Finish Line probation.”
Notable needle drop: Ya Boy’s “Barbershop,” yet another argument that no major metropolitan area has gotten shorter shrift from major rap labels than the Bay.
26. “Oh, Mandy”
Season 2, Episode 8
What happens: E learns (nearly) the full extent of Vince’s past relationship with Mandy Moore and begins to worry that it could sink Aquaman.
Stock up: Drama, whose excitement about an offer for a Joe Mantegna and Brooke Shields movie of the week can’t even be dampened by a road rage arrest.
Stock down: Ari, who is dropped from a magazine’s 40-under-40 package in the middle of a photo shoot when it’s revealed, by Josh Weinstein, that he’s been lying about his age.
Notable needle drop: Vener et al.’s relationship with Shady Records clearly went beyond the marquee names: Stat Quo’s “Like Dat” demands a better place in history.
25. “Three’s Company”
Season 3, Episode 6
What happens: After it’s revealed that Warner head Alan was never going to let Vince do Medellin, Ari begs Vince to honor his contract.
Stock up: Both Lloyd and Drama, as the former gets the latter an audition for the Ed Burns–produced pilot that will become Five Towns.
Stock down: Twenty-four hours earlier, Vince thought he’d found a way to shoot Medellin and Aquaman 2 back-to-back. Now both projects are moving on without him—with Benicio del Toro and Jake Gyllenhaal, respectively.
Notable needle drop: Cherish’s “Do It to It,” playing as E and Sloan clumsily attempt to have a threesome with Sloan’s friend.
24. “Sorry, Ari”
Season 3, Episode 12
What happens: After the Ramones debacle, Vince takes meetings with other agencies.
Stock up: As he points out when he’s the lone voice arguing that Vince should stick with Ari: Drama, who will soon be able to sign with any agent he wants.
Stock down: Bob Ryan (Martin Landau)—an executive who made an illustrious, lucrative career off the backs of artists—is himself swallowed up by the system he helped create.
Notable needle drop: Ted Nugent’s “Stranglehold” at the moment Vince finally fires the only agent he’s ever had.
23. “Dominated”
Season 3, Episode 3
What happens: The gang’s old friend Dom (Domenick Lombardozzi), fresh out of prison, shows up unannounced.
Stock up: Must be nice to trawl Star Maps, break into your childhood friends’ home, and end up hired as a movie star’s head of security.
Stock down: It’s always a tough break when you try to force a child star to stop seeing your 13-year-old daughter, as Ari does here, only for that child star to mock the size of your new boutique agency.
Notable needle drop: Opening a victory lap episode with Frank Sinatra’s “I’ve Got the World on a String” is perfect for the kind of guy who moves to L.A. and makes New York his whole identity.
22. “What About Bob?”
Season 3, Episode 11
What happens: Ari oversteps his bounds, cutting Bob out of the Ramones movie pitching process, and gets the project hip-pocketed by Warner.
Stock up: Turtle, who, after failing to secure the limited-drop sneakers he coveted, receives a one-of-one pair from their famous, reclusive designer.
Stock down: Vince, who pays $20,000 for those shoes before learning that he’s once again unemployable.
Notable needle drop: Cam’ron’s “Down and Out,” which plays over the audio of Drama masturbating in his trailer before shooting a big monologue.
21. “Busey and the Beach”
Season 1, Episode 6
What happens: The gang does Shauna a favor by attending Gary Busey’s art opening. Ari tries to wow Vince with an array of studio movies; when he gets word that the gang is at a party hosted by Josh Weinstein, he storms off to Malibu and asserts his influence.
Stock up: Busey, who explains to Turtle exactly how he could snap his sternum in a single blow.
Stock down: Josh, who gets humiliated at his current boss’s beach house by his former boss.
Notable needle drop: The Roots’ “Don’t Say Nuthin’,” which soundtracks the moment when Ari storms the beach “like it’s fucking Normandy.”
20. “The Boys Are Back in Town”
Season 2, Episode 1
What happens: The crew returns from filming Queens Boulevard in New York to find Ari adamant that Vince do Aquaman; Vince and E have become enamored of Medellin.
Stock up: Turtle, who swipes Ari’s DHL number to import the New York bagels that L.A. can’t recreate.
Stock down: Vince, apparently. According to Ari, Aquaman is not only the best offer on the table—it’s the only one.
Notable needle drop: “Ghetto Rock” from Mos Def’s much-maligned The New Danger, which plays just before the guys meet Ari’s new assistant Lloyd.
19. “Crash and Burn”
Season 3, Episode 5
What happens: Vince gets Big Boy to play one of Saigon’s tracks on the radio; Warner Bros. sends Vince, E, and Paul Haggis on a fool’s errand to try to squeeze the Medellin shoot into an abbreviated slot in the calendar.
Stock up: The Beverly Hills Aston Martin dealership, which probably isn’t used to a client walking in and putting four coupes on a single credit card.
Stock down: Max Ballard (Cole Petersen), the child star next door who has eyes for Ari’s daughter—and whom Ari recommends to Penny Marshall for a movie that shoots for six months in Kazakhstan.
Notable needle drop: Bubba Sparxxx’s “Ms. New Booty,” which pings incessantly from Turtle’s suddenly irrepressible cellphone.
18. “Scared Straight”
Season 6, Episode 11
What happens: An STD scare inspires E to rekindle things with Sloan, Jamie-Lynn tells Turtle, at LAX, that she doesn’t think their relationship can survive a series she’s filming in New Zealand, and Drama has a health scare during an audition for Melrose 2009.
Stock up: Director Mark Mylod, who stages a key sequence like a superb action movie.
Stock down: Terrance, whose pending divorce knocks a full quarter off the $100 million price he initially quotes to Ari to absorb Terrance’s agency.
Notable needle drop: It’s without question when Ari arrives in the office he was once escorted out of and is now set to buy to Swizz Beatz’s “It’s Me Bitches,” but special commendation to Jamie-Lynn for telling Turtle, “I’m downloading you the new Empire of the Sun album” for period detail.
17. “Tree Trippers”
Season 5, Episode 5
What happens: The gang heads to Joshua Tree to eat mushrooms and decide whether Vince should accept a $3 million offer to star in a children’s movie or hold out hope for Smoke Jumpers.
Stock up: Bullied into dog sitting for Ari, Lloyd and Tom decide to move their planned game night to his house.
Stock down: Ari, whose wife arrives home a day early—to find his assistant and about 30 men partying in their pool.
Notable needle drop: Although probably obligatory, Captain Beefheart’s “Electricity” slots in perfectly.
16. “I Wanna Be Sedated”
Season 3, Episode 10
What happens: A day of frustration—Saigon no-shows for the signing of his record deal, E is foisted on an aging producer—ends with a new dream project for Vince: a Ramones biopic.
Stock up: Saigon’s old manager (an electric Hassan Johnson), who strong-arms Turtle out of the rapper’s career.
Stock down: Drama, who’s dangled by goons off a hotel balcony—especially because he wishes Turtle could have held out longer: “I think I could have made the pool.”
Notable needle drop: “Writer’s Block” by the Pharcyde’s Fatlip, an indie mirror image of the post-2001 creep in mid-aughts rap production.
15. “Whiz Kid”
Season 8, Episode 4
What happens: The infamous episode in which Vince wears a fake penis to smuggle clean urine into a drug test.
Stock up: Billy Walsh, who connects Vince with the fake-dick supplier. “Fooled a girlfriend of mine for a week.”
Stock down: Dana Gordon thinks that she and Ari are making a long-delayed connection, only for him to take her to Bobby Flay’s restaurant to provoke the man who’s dating his wife.
Notable needle drop: Brand Nubian’s “Don’t Let It Get to Your Head,” a groaning pun but a certified classic.
14. “Sorry, Harvey”
Season 4, Episode 4
What happens: Hoping to have his condo annexed into Beverly Hills, Drama brings that city’s mayor (Stephen Tobolowsky) out for a night at the club with the guys—where E has to tell Harvey, once again, that he’s squelching a deal.
Stock up: M. Night Shyamalan, who—despite being widely derided for the cameos he makes in his own movies—is wildly funny when he lures Ari to the cemetery where he’s shooting an American Express commercial so that he can give him a script.
Stock down: The owner of a black Lexus that a valet mixes up with Ari’s; his wife demands to know why he had been at that particular restaurant that evening.
Notable needle drop: 2Pac’s “All Eyez on Me” over the closing shot of the mayor as he’s captured by TMZ getting into a car with the frequent Howard Stern guest he meets at the club.
13. “Pie”
Season 5, Episode 9
What happens: As Smoke Jumpers begins to shoot, Vince clashes with his costar Jason Patric, who keeps stealing his lines, and Verner, who clearly has little interest in him.
Stock up: Lloyd, whose attention to detail uncovers a surprising underlying truth in the financial records of …
Stock down: Andrew Klein, Ari’s friend of many years, who became a TV agent in the Valley and who asks him for a loan to keep his business afloat.
Notable needle drop: Slick Rick’s “Children’s Story”
12. “The Scene”
Season 1, Episode 7
What happens: Vince and E meet Billy Walsh, the Sundance-winning wunderkind tapped to direct Queens Boulevard.
Stock up: The Crazy Girls dancer who gets her rent covered by Drama.
Stock down: Crazy Girls itself, whose buffet was downgraded to a B by the health department.
Notable needle drop: Creedence Clearwater Revival’s “Run Through the Jungle,” which rattles Billy’s Chateau Marmont suite.
11. “Guys and Doll”
Season 3, Episode 4
What happens: Dom is accused of stealing the original Shrek doll from the home of the producer who’s considering Vince for Medellin.
Stock up: Vince, but probably too far. He’s about to learn just how restrictive a successful franchise can be.
Stock down: As falling stock goes—and as the guys note after Dom’s been banished—an apartment and a Hummer isn’t a bad severance package.
Notable needle drop: The from-zero drop of Dead Prez’s “Hip-Hop” over the news that Medellin and Aquaman 2 have the same scheduled start date.
10. “Exodus”
Season 2, Episode 13
What happens: Drama and Turtle trail Mandy, whom they suspect of cheating on Vince with her ex-fiancé, while Terrance returns to work full-time and pushes Ari out of the agency.
Stock up: Lloyd, who to this point has played only in the fringes but is finally able to exert some leverage over Ari.
Stock down: Vince, who’s finally, utterly destroyed.
Notable needle drop: Stevie Wonder’s “For Once in My Life,” which Ari and his wife dance to outside their house after he’s been fired.
9. “The Dream Team”
Season 4, Episode 5
What happens: An excellent trailer for Medellin leaks, enraging Billy as he, Vince, and E are pitched to Interview magazine as the brain trust behind the movie.
Stock up: One of the joys of television is seeing characters who are described as being excellent at their jobs in fact delivering on that promise; Ari’s manipulation of Josh Weinstein, to make Heath Ledger drop out of a project Ari wants for Vince, is, as Lloyd concedes, “brilliant, complex.”
Stock down: L.A. medical screening policies. When Drama becomes fixated on the trucker hats sold by a particular weed dispensary, he goes to get his card, leading to my favorite joke of the entire series. He refuses to claim that he has nerve damage like everyone else in the waiting room; when his name is called, Turtle asks, “What are you gonna go with?” to which Drama replies, “My improv skills.” Hard cut to a doctor (Bob Balaban) saying, “You have Legionnaires’ disease?”
Notable needle drop: Turtle smoking weed to Dilla’s “Won’t Do.”
8. “Manic Monday”
Season 3, Episode 15
What happens: Vince and E struggle to tell Amanda that they want to pass on the Edith Wharton movie; Ari has a meltdown when he realizes that his grief about losing Vince has caused him to lose his edge.
Stock up: Ari and his wife’s couples therapist (Nora Dunn), who has a real shot at that club record she’s shooting for when Ari interrupts her for an emergency session.
Stock down: A manager’s role is significantly diminished when a client and his agent start sleeping together.
Notable needle drop: Few moments highlight the absurdity of Entourage—and of the entertainment industry as a whole—like Beanie Sigel and Freeway’s “Roc the Mic,” which plays as Ari waltzes into his office to fire an agent who just had LASIK surgery.
7. “Play’n With Fire”
Season 5, Episode 11
What happens: Verner fires Vince from Smoke Jumpers, which leads to a confrontation that escalates above the studio level and to its parent company, eventually shutting down the film.
Stock up: The only person who comes out unscathed is Turtle, who slinks away at 4 a.m. to answer an invitation from Jamie-Lynn.
Stock down: The aftermath of the Smoke Jumpers firing leads to Vince’s absolute career nadir; the episode ends with him and the crew piling onto a plane to head back to Queens.
Notable needle drop: Rammstein’s “Du Hast” when Verner storms through the corporate hallways.
6. “The Abyss”
Season 2, Episode 14
What happens: After Mandy leaves him for her ex-fiancé, Vince decides to quit Aquaman, firing E—who is offered an agency job by Terrance—and Ari, who scrambles to set up his own shop.
Stock up: James Cameron, who can yank the most miserable, solipsistic millionaires out of a tailspin.
Stock down: A brilliant Richard Schiff, who has to browbeat Ari for neglecting him during their meeting at a Coffee Bean.
Notable needle drop: With all credit to the season-ending “Gimme Shelter” drop, it’s DJ Quik’s wistful “Does the Goodlife Exist.”
5. “ReDOMption”
Season 5, Episode 6
What happens: Dom is arrested after a police chase and needs to be bailed out of jail so that he can tell his wife what happened.
Stock up: Domenick Lombardozzi. There are few actors—TV guest stars or otherwise—who can carry this episode’s comic moments (deadpanning that he’s likelier to jump bail once he learns that it was E who posted it) and sell the abandonment he feels as his wife speeds away with their newborn.
Stock down: For a time, it’s Ari, who loses tens of thousands of dollars—and then the chance to cast Vince in Smoke Jumpers—to Alan Gray on the golf course. Fortunately for him, Alan never makes it off that course, dying of a heart attack on the green where he’s just yelled at Ari.
Notable needle drop: Snoop and Dre’s “Imagine,” which plays over the end credits, is one of the arch-examples of Entourage’s take on then-contemporary rap.
4. “The Sundance Kids”
Season 2, Episode 7
What happens: Vince finally gets the Aquaman offer from James Cameron; E enrages the show’s delightfully thinly veiled Harvey Weinstein stand-in.
Stock up: Cameron, who gamely wears a parka while standing in the concession line of what is clearly the Vista on Sunset Boulevard in Los Feliz, standing in for Park City.
Stock down: Drama and Turtle, who spend the entire festival competing over their volunteer driver. “Why don’t you guys show me your bunk beds?” will haunt both men for months.
Notable needle drop: For some reason, one of the strongest sense memories I have of Entourage is the inexplicable slow-motion opening shot of this episode, soundtracked by “Wanna Know” from the forgotten second Obie Trice album. But the best pull is Bump J’s “Move Around.”
3. “Vegas Baby, Vegas!”
Season 3, Episode 9
What happens: The boys kidnap Ari to accompany them on a weekend trip to Vegas, where Vince takes on a terrified Ari as a gambling partner and Drama is able to reunite with his beloved male masseuse.
Stock up: You have to admire Turtle’s industriousness, cutting deals with every single contestant in the strip club beauty contest. Uniform grift.
Stock down: Seth Green and his crew, who get beaten to a pulp by E, Drama, and Turtle.
Notable needle drop: Nothing sounds more like the beginning of a promising night at the tables than Camp Lo’s “Luchini.”
2. “Return of the King”
Season 3, Episode 17
What happens: Ari tries to secure the complex series of sign-offs needed to make Vince a last-minute replacement in Medellin—on Yom Kippur, which means a lot of walking between temples and quiet calls on contraband cellphones.
Stock up: The legendary comedian Shelley Berman, who appears in exactly one scene of the series to pick at the spread of food before sundown; when Ari’s wife reprimands him, he says, “Sorry, sorry, I’m a bad Jew: Shoot me.”
Stock down: The horse Drama buys from a trainer, then tries to pawn off on Ed Burns.
Notable needle drop: The Pharcyde’s “Runnin’,” which plays over the closing credits after Vince has fired Amanda—and is immediately made to second-guess his decision.
1. “One Day in the Valley”
Season 3, Episode 2
What happens: As Ari and E sweat over Aquaman’s chances of beating the studio’s $95 million opening-week projection, Turtle gets Vince excited about beating Spider-Man’s record—while sweltering heat and rolling blackouts threaten theaters on the West Coast and trap the guys north of the city, and they go through the motions of accepting failure until it becomes clear that they never needed to.
Stock up: The pair of high school geeks who not only get into a house party with Vince’s help, but also take over the lease on E’s Maserati.
Stock down: Ari’s poor wife, who has to call in professionals just to get him to sleep with her.
Notable needle drop: “I Just Want to Celebrate” by Rare Earth, which, over these end credits, plays like relief more than anything else.
Paul Thompson is the senior editor of the Los Angeles Review of Books. His work has appeared in Rolling Stone, New York magazine, and GQ.
