One of the main draws of Quentin Tarantino’s latest film, Once Upon a Time … in Hollywood, is getting to watch two of the biggest movie stars on the planet—Leonardo DiCaprio and Brad Pitt—finally share the screen together outside of a lavish casino commercial. But while all the movie’s bromantic Brad-Leo exchanges live up to the hype, the two are far from the only big names in this Hollywood epic, which, even for Tarantino’s standards, is quite the casting flex. The likes of Tim Roth, James Marsden, and Danny Strong didn’t leave the cutting room floor!
So to commemorate Once Upon a Time … in Hollywood’s bountiful cast—and because ranking things is to The Ringer what a good spanking is to Chuck Rhoades—I’ve ranked the 20 most prominent characters from the film. To talk about the performances, I’ll have to dive into some spoilers; avert your eyes while you can. And if you disagree with the rankings, please keep it to yourself or I will have to borrow Rick Dalton’s flamethrower.
20. Gypsy (Lena Dunham)
No.
19. Charles Manson (Damon Herriman)
Herriman has the dubious honor of playing the infamous cult leader in two productions this year—the other being the second season of Mindhunter, coming in August. I expect the Netflix series will give Herriman a lot more to do, as Manson spends almost the entire film off-screen. Tarantino, unsurprisingly, holds a lot of contempt for the Manson Family, so relegating Manson to such a minimal role is its own form of shade. But it also means Herriman is given next to nothing to work with, which renders the performance unmemorable—even if that’s the point.
18. Steve McQueen (Damian Lewis)
This should be iconic: Bobby Axelrod himself as the King of Cool—and forced not just to wear a wig, but to make his mouth normal-sized. (By all accounts McQueen, unlike Lewis, had a normal human mouth.) Alas, Lewis-as-McQueen is in the film only to provide a brief exposition about Sharon Tate’s relationships with Roman Polanski and Jay Sebring; he’s gone as quickly as he enters the frame. It’s likely that McQueen was meant only for a bit role, but given how difficult it is for Lewis to keep his thicc British accent in check, maybe it was for the best.
17. Jay Sebring (Emile Hirsch)
The Hollywood hairstylist was one of the victims of the attack that left Tate and four others dead—though, like Inglourious Basterds and Django Unchained before it, Tarantino’s film luxuriates in a revisionist revenge fantasy. (In this case, the Manson Family gets its bloody comeuppance.) Sebring’s best moment arrives at the very end of the film, when he marvels at Rick Dalton’s account of three hippies invading his home and outs himself as a Dalton fanboy in the process. But since the movie has a placid retelling of what happened in the Tate household—as in, nothing at all—Sebring’s minimal role isn’t particularly memorable.
16. Squeaky Fromme (Dakota Fanning)
Fanning’s character sole purpose seems to be stoking the flames for one of the internet’s favorite Tarantino bits: The dude is really into feet. (Just ask Uma Thurman.) Either Tarantino is very self-aware, or Fanning’s grimy hippie toes are his latest muse.
15. Charles “Tex” Watson (Austin Butler)
To quote a character from another Tarantino movie: I like the way you die, boy.
14. Wayne Maunder (Luke Perry)
In what ended up being his final film role before his death in March, Perry plays a prototypical good guy on the set of a Western. (Leo’s Rick Dalton is the over-the-top villain with a killer ’stache.) It’s not a particularly showy role, but Perry’s presence brings an added gravitas that’s unavoidable given the circumstances. Perry was known for most of his career as a lovable teen heartthrob, so it feels appropriate that his last role is a saintly cowboy clad in white.
13. George Spahn (Bruce Dern)
The role, which was initially meant for Burt Reynolds before his death, marks the third consecutive appearance in a Tarantino film for Dern, who shares a scene with Pitt’s Cliff Booth at his ranch. In real life, Spahn did allow Manson and his followers to stay at the Spahn Ranch; in exchange, the women of the cult had sex with him. The best thing that can be said about Dern’s performance is he’s very convincing as a sad, blind old man.
12. Marvin Schwarz (Al Pacino)
Schwarz tries to convince Dalton, who doesn’t realize he is super washed, that his future is in filming spaghetti Westerns in Italy. Dalton believes such films are beneath him; it doesn’t help that Pacino plays Schwarz like your stereotypical smarmy casting agent. It’s the kind of role that late-stage Pacino was born to play—and would probably be his peak of 2019 if he weren’t also starring in Martin Scorsese’s The Irishman later this year.
11. James Stacy (Timothy Olyphant)
It looked like Olyphant had just stumbled off the set of Deadwood—in a good way.
10. Pussycat (Margaret Qualley)
One of the more beguiling presences in the film, Pussycat comes across like a quintessential hippie, all the way down to her unshaved armpits. After getting picked up by Cliff, she tells him that being a stuntman is way cooler than being an actor, since they fake deaths on-screen all the time while real people die in Vietnam every day. But her bubbly exterior reveals something a lot creepier when Cliff drops her off at the Spahn Ranch. Qualley plays the notes perfectly—naive, but in a dangerous sort of way—and is the most memorable character introduced from the sprawling Manson Family.
9. Stuntman Randy/The Narrator (Kurt Russell)
In voicing the narrator in Once Upon a Time … in Hollywood, it’s unclear whether Stuntman Randy the character is also providing the exposition, or whether Tarantino was merely soothed by Russell’s soothing drawl. (Could it be both?) Nevertheless, pulling double duty allows Russell to flex his charms and make a larger imprint on the movie; a win for all parties involved, including the audience. Though it would’ve been cool if Goldie Hawn also made an appearance.
8. Francesca Capucci (Lorenza Izzo)
Capucci is Dalton’s wife—whom he meets during the six months he spends in Italy shooting spaghetti Westerns. Francesca went from a near nonentity into top-10 consideration when she began beating the shit out of a Manson Family intruder. The cursing in Italian as she knocked the would-be murderer on the ground? Perfetto!
7. Sam Wanamaker (Nicholas Hammond)
Hammond isn’t a household name; he’s best known for playing little Friedrich von Trapp in The Sound of Music. Perhaps starring in one of the defining movies of the ’60s makes Hammond’s presence in Once Upon a Time … in Hollywood a bit of stunt casting, but as the director Sam Wanamaker, he’s also gloriously eccentric. The best way to describe Wanamaker is that he reminded me a lot of Conner O’Malley’s sleazy music manager shouting “IT’S GONNA BE A HIT!” from the “Laser Spine Specialists” sketch of I Think You Should Leave. And if that reference doesn’t mean anything to you, go watch I Think You Should Leave right now.
6. Bruce Lee (Mike Moh)
Moh, a noted Bruce Lee enthusiast, does his best to infuse his brief appearance with the same fun, kinetic energy you’d expect from a dude who once fought Kareem Abdul-Jabbar on-screen. Lee’s fight against Cliff in a studio parking lot is among the film’s funniest tangents, and by the time you get home from a screening, you’ll probably fall into a Bruce Lee YouTube wormhole—or alternatively, you can check out Cinemax’s Warrior.
5. Sharon Tate (Margot Robbie)
There’s been some controversy over Robbie’s minimal dialogue in the film, but when Tate does appear she infuses the project with the kind of warmth rarely seen in Tarantino’s violent filmography. During the movie, Tate is on the rise, still soaking up the nascent stardom just as Dalton’s beginning to fade away. The murder of Tate and her houseguests is cited as the symbolic death of the ’60s, and is, undoubtedly, one of the most shocking and tragic moments in Hollywood’s history. Tarantino’s revisionist Hollywood history isn’t just wistful for a bygone era, but a surprisingly humane tribute to an actress whom the auteur wants to be remembered for more than just her final moments.
4. Brandy the Dog (Sayuri)
Move over, Charlie Cooper: There’s a new, very good candidate for the Palm Dog. The pit bull is the breakout star of Tarantino’s bloody crescendo, attacking the Manson Family assailants and even getting a good chomp of Tex’s junk. As Cliff is stretchered off to the hospital, we find out Brandy is snuggling in bed with Francesca. And, you know, for preventing three hippies from committing some grisly murders under his own roof, BRANDY DESERVES ALL THE CUDDLES IN THE WORLD.
3. Trudi (Julia Butters)
This precocious 8-year-old would run circles around the Big Little Lies kids. A method actor in the spirit of Daniel Day-Lewis, Trudi immediately makes an impression on Rick during the set of a Western, sitting in an oversized chair reading through a lengthy Walt Disney biography. Also: She wants to be addressed only by her character’s name on set; she doesn’t like cutesy nicknames; she tells Rick that perfection as a performer isn’t attainable, but rather, “it’s the pursuit that’s meaningful.” This is all funny because, you know, she’s 8, but the actual performance by Butters, holding her own next to Leonardo DiCaprio, almost feels like a passing of the torch. Later, when Trudi calls Rick’s acting some of the best she’s ever seen, that twinkle in his eye—the one that became a dank meme when the first Once Upon a Time … in Hollywood trailer dropped—is funny, yes, but feels like genuine affirmation; this Tiny Meryl Streep is not fucking around. I would take a bullet at the saloon for little Trudi.
2. Cliff Booth (Brad Pitt)
Playing to his strengths, Pitt approaches Cliff a laconic presence throughout the movie, just as content watching TV with his dog as he is challenging Bruce Lee to a fight in a parking lot. (Though it’s certainly bad on many fronts that he, uh, definitely killed his wife.) But Cliff was fun to follow throughout the film, and that was before he tripped on an LSD-soaked cigarette and thought the Manson intruders were some kind of psychedelic fabrication at Dalton’s residence. Unfazed by their threats, his stuntman skills are put to efficient use; he takes little time killing two of them with his bare hands, with the third careening through Dalton’s glass panel and into the swimming pool. (Dalton screaming “What the fuck?!” on his floatie absolutely wrecked me.)
1. Rick Dalton (Leonardo DiCaprio)
It’s the role Leo was born to play—specifically at this moment in his career. Once Upon a Time … in Hollywood is wistful about the ’60s, yes, but it’s also a movie about the trials of a person suddenly coming to the realization that they’re washed. (Not that Leo is washed as an actor, but when’s the last time this dude dated anyone close to his age?!) By 1969, Dalton is Melo refusing to come off the bench.
There is perhaps no better actor than Leo for capturing the creeping anxiety and existential crisis that’s beginning to envelop Rick Dalton, as well as the catharsis Dalton feels when his neighbor and the next Big Thing in Hollywood, Sharon Tate, invites him over for a drink after the chaos that unfurled at his home—a lifeline to make sure he doesn’t fade into obscurity. It’s about as satisfying as Leo finally winning an Oscar after eating raw bison liver and getting wrecked by a bear.
