Doug Liman had a decision to make. Getting In, the movie he’d directed right after getting out of USC film school, had gone straight to video. But then 1996 brought his indie sensation, Swingers. Made for only $250,000, it followed the lives of crying and carousing unknown actors in Los Angeles. Its release attached a scotch-powered jetpack to the careers of Vince Vaughn and Jon Favreau. Swingers earned $4.55 million at the box office, though it found an even greater audience once it hit the home video market. It’s had such a deep cultural impact that 23 years later, jag-offs are still yelling “Vegas, baby!” when their planes touch down at McCarran.

So what was Liman going to do next?

To the delight of his representation, major film studios were offering him comedies with budgets in the low $20 millions. He was heading toward Heartbreakers, a film about a mother-daughter conwoman team written by the guys behind Liar Liar and The Little Rascals. Then one day, when Liman was leaving his Manhattan apartment, he heard his phone ringing as he stood in the hallway waiting for the elevator. He was hoping it was a girl, but it turned out to be the producer Mickey Liddell, pitching him to direct a movie called Go.

The film told three interlocking stories, each tied to an ecstacy deal initiated in the checkout line of a cruddy Hollywood supermarket. It featured crackling dialogue, a Christmas-themed rave, closeted soap opera stars, a car chase on the Vegas strip, Beverly Hills, 90210 jokes, iodine poisoning, a tantric threesome, and a telepathic cat named Huxley.

Even before the phone call, Liman felt like Heartbreakers was too easy, that it was too much money for a comedy. Go had a proposed budget around one-fifth of what he’d spend on Heartbreakers. His agent cautioned that if Liman did another indie and things went down in flames, he wouldn’t get the opportunity to work with a major studio again. On the other hand, if he completed Heartbreakers now, regardless of how well it did, his career would be set.

Unlike other marquee indie directors of the era, Liman wasn’t a writer, so he wasn’t generating his own material. It was the ethos driving Go’s script that convinced him to pick the project. “I had a charmed youth in that I did a lot of crazy things and no one ever got hurt,” Liman says. “I had this belief that you have a get-out-of-jail-free card when you’re 18. And I recognize there’s a lot of white privilege connected to that get-out-of-jail-free card now that I wasn’t as sensitive to at the time because I only knew my own experience.”

“What I saw in Go was a story that was celebrating: Do crazy shit while you’re young,” he continues. “You can get away with it when you’re young.”

When you talk to people who’ve worked with Liman, they’ll describe him as “a character and a half” or “an interesting cat.” What they mean is that he’s a weirdo who makes preposterous choices that should result in failure but often end in success.

Looking at Go now, 20 years after it was released in April 1999, you can see a convergence of several film trends of that era. There’s the absorption of the creators of 1990s indie cinema into the mainstream moviemaking landscape. There’s a new generation of bright young actors ready to make the leap from teenage fare to more adult material. There’s Quentin Tarantino’s cinematic quirks becoming modern conventions. Yet throughout the making of Go, there was moment after moment that should have led to disaster. Still, things managed to work out. Sort of.

Go wasn’t an abject financial disaster, but it was far from a hit. It’s not quite a cult classic, but over the years it’s built a contingent of dedicated fans. Assistants squealed when I told them which film I wanted to interview their bosses about. Lauded careers were launched off of it. Over the two ensuing decades, the amount of success that’s come to the people involved in the film—from the actors, to the crew, to the studio executives who got involved—is incredible.

Liman has made other films that have grossed far more money, like Mr. & Mrs. Smith and The Bourne Identity. Some of his work is more beloved by film devotees, like Swingers and Edge of Tomorrow. Still, Liman considers Go his best film. “We’re so trained toward short-term rewards that the true success of a movie has to be evaluated in 10 or 20 years after it comes out, and so, if you ask how I feel about how [Go] was received from where I sit today, I couldn’t be more proud of it and it couldn’t have been received better,” Liman says. “I do like films, like Mr. & Mrs. Smith, where you do get some huge opening weekend, but if I had to trade one or the other, it lasting and being something that people will watch today is something that is more important to me.”

There’s a scrappiness to Go that could only have been generated by a group of people who, much like the movie’s characters, often found themselves in situations where they were in over their heads. As the film’s editor, Stephen Mirrione, says, “One of the things I like about [Go] is it’s a movie about idiots that’s made by a bunch of goofballs, a bunch of knuckleheads.”

Sitting inside his home in L.A.’s Hancock Park neighborhood, screenwriter John August repeats one of his maxims: “My favorite genre of movie is movies that get made.” His filmography includes Big Fish, the Charlie’s Angels adaptation from 2000, the Charlie and the Chocolate Factory remake, and the forthcoming live-action Aladdin. But back in 1998, when he was nearing the end of his 20s, nothing August wrote had made it to the screen. He’d been hired to adapt How to Eat Fried Worms for Ron Howard at Imagine Entertainment and A Wrinkle in Time for Dimension/Miramax, neither of which was anywhere close to being made. “I was really fortunate to be getting those jobs,” he says, “but I was only being considered for movies involving gnomes, elves, dwarves, and Christmas.”

To expand the type of offers he was getting, he returned to a script for a short film called X that he wrote while enrolled in USC’s graduate film program. X is basically the first segment in Go. It tracks a young supermarket worker on the verge of eviction named Ronna who gets caught up in an ecstacy deal and ends up lying in a ditch outside a rave. In his head, August had already built out more of a backstory for Adam and Zack, the two guys who come into the grocery store looking to score, and Simon, Ronna’s English coworker who usually deals to them. For Go he created two more segments that focused on these characters and increased the connections among all three parts.

There had been movies that had broken up the narrative and told related stories from different perspectives before—most famously Akira Kurosawa’s Rashomon and Jim Jarmusch’s Mystery Train—but those were the type of movies mostly taught at film school or shown at sticky-floored repertory theaters. Then 1994 brought Quentin Tarantino’s Pulp Fiction, which managed to popularize the concept. “The idea of restarting your movie was fine; it wasn’t just an experimental art-film kind of thing,” August explains of Pulp Fiction’s impact. “It was a thing that people could have said, ‘Oh, it’s like that.’ The ‘Oh, it’s like that’ has sort of been a blessing and a curse. It made it possible to make [Go], but also made it really easy to dismiss the film or to dismiss that gimmick as ‘Pulp Fiction did it first.’”

(It might not help that along with the pop-culture-peppered dialogue, Go also features two Tarantino-style trunk shots.)

When August began taking meetings for Go, the big studios were still buying spec scripts. But the real motivation was to show them what he was capable of. Because of its tonal shifts, Go could be read as an action movie, a comedy, a thriller, or whatever sample they needed it to be. Executives would tell August they loved his script, but they couldn’t make it. Instead they gave him dialogue-polishing work or offered him other gigs that didn’t involve gnomes.

Then Banner Entertainment, a small production company, decided it wanted to put together Go as an independent feature with a $3.5 million budget, and it would bring August on as a coproducer who would be on set every day. Liman was always at the top of the list for director. “Doug, to this day, doesn’t take ‘no’ for anything, and it’s probably his strongest quality as a director,” says August. “He wasn’t scared of anything in the script.”

To assemble the large ensemble, they brought on Joseph Middleton, a casting director who was still diversifying his résumé. No one was attached to the film, so Middleton had a blank slate when filling out the roles. He had seen Taye Diggs in a production of Rent, so he had Liman fly out to New York to meet him for the part of Marcus, Simon’s far more capable friend. He booked Katie Holmes to play Ronna’s hesitant coworker, Claire, when she had only shot the pilot for Dawson’s Creek and before the show turned her into a Rolling Stone cover star. Timothy Olyphant came in to audition for Zack or Adam and ended up with the role of the not too menacing drug dealer Todd Gaines. Middleton even got Melissa McCarthy in her first film role for a memorable one-scene appearance.

Middleton, who is now the head of casting for Paramount Pictures, continued working with Liman through the 2008 sci-fi action film Jumper. “The one thing I think about our relationship from the very beginning, and now I’ve known him for many years, is that he always made me defend who I thought was right,” says Middleton. “In that process I always knew if I was right, because I could fight for it.”

Even though Go was an indie, it quickly became a project that lots of young actors wanted to be a part of. “When they’re casting these ensembles, you go to the audition and you know everybody,” says Breckin Meyer, who won the role of Tiny, a white boy who is convinced his mother’s mother’s mother was black. “It’s every young actor you know. You go in there and you go, ‘Oh, it’s Seth Green. It’s this dude, Scotty Caan.’ And it always comes down to: We all like this thing. I wonder who’s going to get it? With Go, everyone knew it was a very cool script.”

For the role of Ronna, Liman and Co. were determined to cast Sarah Polley, a Canadian teenager who had already soured on Hollywood. Though Christina Ricci was considered for the part, Polley remained the target. “I was a little bit obsessed,” Middleton confesses. (One of the few major differences between August’s spec script and the final film is that in the original, Ronna is African American.)

Polley’s performance in Atom Egoyan’s film The Sweet Hereafter convinced Liman that she was right for Ronna. “She just had this intensity in a young person I had never seen before,” he says. “Then when I met with her, clearly she was the best young actress working. I’m sure it was like meeting with Meryl Streep early in her career.”

But before that meeting, Polley declined the role several times. “Every way in which they would’ve been pitching this movie to her is her worst nightmare,” says Liman. “Hot up-and-coming director who won MTV’s best new filmmaker award. That’s not the kind of movies she’s interested in being in.”

When the producers found out Polley was coming to L.A., they told her agent that if she didn’t take a lunch meeting with Liman they wouldn’t see any other clients for the film. So the two got together and as Liman described Go, she became intrigued. She told him she would read the script as she flew home to Toronto. Liman told her he’d send her a copy, but she explained that a car was waiting for her right then to take her to the airport and she was incredulous that he hadn’t thought to bring a script with him.

Liman ran to his car and rummaged through the mess in his trunk, looking for a copy. He found the script he’d passed to his editor, Mirrione, for notes. Liman and Mirrione had been working together since Liman’s student thesis film, and while Mirrione is direct with his opinions normally, when communicating with Liman he felt the freedom to be particularly harsh. “I look at the script because I know [Mirrione] had marked it up a little bit,” Liman recalls. “So I open it up and there’s a line circled and he’s written, ‘Stupid.’ And I flip to the next comment and he’s like, ‘Dumb line.’ I flip a few more pages and it says, ‘This makes no sense.’ Flip a few more pages and it says, ‘Why???’”

With no other options, Liman gave Polley the script anyway. He is now convinced that it was this unexpected, and what some might call unprofessional, decision that ultimately won her over. “Sarah’s become a very close friend,” he says, “Knowing her personality, it was going to take something that drastic to get her to see that this was not going to be a traditional Hollywood movie.”

Then, with filming set to start in a few weeks, Banner Films producer Liddell learned that all the financing had dropped out. Without notifying anyone else, he sent the script to Harvey Weinstein, since Miramax had distributed Swingers. On a Sunday, Weinstein passed on the project, so Liddell informed the other producers and Liman that Go was dead. (Liddell declined to comment for this article, saying that he was on location in France for a project.)

Undeterred, Liman, August, and producer Paul Rosenberg (who died in 2015), came into the film’s office on Monday morning looking for ways to revive the project. Liman and August didn’t have the connections to get the movie made, but Rosenberg, a former executive, began making calls as production assistants Xeroxed copies of the script and ferried them around town. “Paul was just calling up anybody he knew, anywhere in the business, and being like, ‘We have this amazing cast, a great script,’” says Liman. “Then he’d pass the phone to John August or myself to keep talking about the movie and he’d get on the phone with somebody else.”

On Tuesday, they met with Ricky Strauss and Andrea Giannetti, two young executives at TriStar, a division of Sony Pictures. Strauss and Giannetti quickly convinced their bosses to take on Go as what was essentially a negative pickup deal, where the studio agrees to purchase an indie for a set dollar amount (regardless of whether it goes overbudget) in return for a split of the profits. “People were head-scratching a little bit about how high-concept [Go] was and how marketable it could have been, but it was such a good script, and people really wanted to be in business with Doug Liman and John and the cast,” says Strauss, who now works as the president of content and marketing for the forthcoming Disney+ streaming service.

By Wednesday, Liman was back scouting locations around L.A.

When Liman signed on, one of the first things the producers told him was that the car chase on the Las Vegas Strip that concludes the film’s second act would have to be cut for budget reasons. Liman instead decided to shoot the car chase as if he were helming a major studio film, dedicating almost a third of his budget to the scene and scrimping in other ways throughout the rest of the production. (With Sony’s involvement, the budget got bumped up to about $5 million, but all the extra money went toward making it a union- and Directors Guild–compliant shoot.)

He employed many of the cost-saving techniques he’d developed on Swingers. He shot it on an Aaton 35-millimeter, a camera usually reserved for making documentaries in the days before everything went digital. He could reload the Aaton with film in a matter of seconds, while for traditional cameras it took at least four minutes and caused delays in shooting as everyone used those opportunities to relight the scene or take breaks. The only problem with the Aaton was that it isn’t constructed for recording dialogue and makes as much noise as a sewing machine, so Liman would wrap it in a down jacket as he filmed. “Jon Favreau used to describe acting in Swingers like acting for a big fluffy snowball,” says Liman.

While making Swingers, instead of trying to manufacture settings, Liman would just film scenes that took place in parties or at bars in actual parties or bars, using unassuming bystanders as extras. Before anyone got too upset or the police came, he’d be gone. For Go he adopted a similarly frenetic pace.

Some actors, such as James Duval, whose first films included Gregg Araki’s microbudgeted teen apocalypse trips Totally F***cked Up and The Doom Generation, were used to Liman’s approach. “[Go] still had a little bit more money, so we were running and gunning it, but not in the guerrilla style that I actually was used to,” Duval says. “That was really getting kicked out because you didn’t have money for locations. We had permits on [Go], which was a wonderful thing.”

For others it was an adjustment. Jay Mohr had been booking lots of parts after his role in Jerry Maguire, but Go was a different type of production. “He showed up exhausted because he had been out partying the night before for his first day of shooting,” says Liman. “By the end of the day he was like, ‘Jesus Christ, I haven’t been able to go back to my trailer once to nap. You literally haven’t stopped shooting.’”

Mohr says he came to enjoy Liman’s method because it reminded him of his work as a stand-up comic in New York, where he’d have to run around to different clubs in the city to get up at as many spots as possible in a night. There was only one occasion on Go when he objected to the breakneck speed. Says Mohr, “I remember in the scene where Bill Fichtner is naked when I come out of the bathroom in his house, I came out one time and he was standing there and I said, ‘Just so you guys know, it’s going to take me six takes to even not burst out laughing.’ And they said, ‘Well, the sun’s coming up, it can’t be six.’ Me not going with the flow for the first time in the movie, I said, ‘Well, you better put some duvetyne over those windows, because it ain’t happening within six. I know how far I can kick this football, and it’s six takes.’”

The production fell behind schedule after only a few days, so the producers asked August to lead a small second-unit crew, picking up insert shots or handling reshoots once Liman moved on. As a result, August says you can often see his hands fill in for other actors on screen, whether it’s a little kid taking money from under a hotel room’s door or Scott Wolf rearranging the contents in the trunk of his Miata. After principal shooting wrapped, August would drive Liman’s Saab convertible around Los Angeles at night as the director stole cutaway shots out of the back.

To trim the budget, Liman acted as his own director of photography and often operated the camera himself, as he had on Swingers. It had an effect on the actors’ performances. “Doug had that camera on his shoulder and it had this immediacy and this feel to it that felt like there was a third eye that was always in the room,” says William Fichtner, who plays the police officer Burke.

Recalling the scene where the cops tape a recording device onto Scott Wolf’s character’s crotch, Fichtner says, “We got in a little tiny bathroom. There wasn’t room for anybody. There was a boom in there, the four actors in the scene, and Doug with his camera. He would move that camera around so seamlessly. I remember that more than anything. And Jay Mohr being a maniac.”

Go was the first movie that Strauss had championed at TriStar, and he visited the set two or three times a week. “It was definitely hectic because there were constant changes,” he says. “The pages would come in the morning or the night before. People would talk about what the blocking was going to look like and how it was going to go, then there were some last-minute changes that were made from rehearsals or from Doug maybe changing his mind about lighting packages or where the scene should take place. And also we didn’t have a ton of money, so it was definitely scrappy, but it was wildly creative.”

Another habit that Liman had developed on Swingers was not turning off the camera between takes, so when screening the dailies, everyone could hear his conversations with the actors. “Doug, sometimes his brain is working on a different frequency than the words that come out, so sometimes what he’s saying sounds a little idiotic, so it’s especially frightening if you’re a producer and you’re spending a lot of money and have all this responsibility,” says Mirrione. “There was one point where I went to Doug and I said, ‘Maybe you should stop talking so much, because they can hear everything you’re saying and I think you’re scaring them, because you sound crazy.’”

Drugs play a major role in Go, but it’s not a drug movie. Both Liman and August say they were never really into mind-altering substances. August says that of all the characters he created for the film, he’s most like Katie Holmes’s Claire, the wet blanket who manages to have more fun than anyone else, despite herself. Liman didn’t see himself in any of the characters, but says he had met a lot of people like Simon, the European eager to take in the full excitement and ridiculousness of the American experience. Desmond Askew, the English actor who plays him, remembers, “I was still growing up at that time. I wasn’t shooting bouncers or stealing Ferraris, but I think that’s what Doug and I talked about, and he really impressed upon me that that was what attracted him to my performance, this kind of wide-eyed sense of wonder. I remember him constantly saying, ‘Just think: puppy dog, puppy dog.’”

Go was also one of the first movies that touched on American dance music culture as it spread from its foundational homes in Detroit and Chicago. For the soundtrack, Liman brought on Julianne Jordan (neé Kelley), the now-celebrated music supervisor who got her first gig in that role on Swingers. Before shooting began, Liman, Jordan, and some of the producers would go to raves around L.A., where the director would surreptitiously steal shots that ended up in the ecstasy-evoking opening credits.

Jordan was able to license tracks by ascendent electronic music acts Fatboy Slim, Leftfield, and Air, but the biggest coup was getting the Orange County ska pop band No Doubt to record the song “New” for the soundtrack. “For No Doubt, who at that time was massive, to say they will write an original song for a 6 million–dollar movie!” says Jordan. “You don’t see Ariana Grande saying she’s going to do that.”

For the film’s score, Jordan recommended that Liman work with BT, a young music producer and DJ who began playing classical piano when he was 4 and enrolled at the Berklee College of Music when he was 15. Liman showed up at BT’s house in Rockville, Maryland, unannounced with his dog and a VHS copy of rough-cut scenes from Go. The artist hadn’t even seen Swingers at that point. “We watched it in my living room,” says BT. “I had a studio in the upstairs of my house at the time. We kept running back and forth to upstairs and I was literally coming up with ideas on the fly.”

Shortly thereafter, BT moved to Los Angeles and still works as a film composer. “It was a special project,” he says. “It was something that had no temp score. I was like, ‘Oh my god, all movies are this awesome. They play you a film without any music in it and you just write whatever you want.’ Cut to me last week. I’m like pulling my frickin’ hair out, the director is going, ‘Can you make it more like the temp?’ And I’m like, ‘Yeah, we’re going to get sued if it’s anything more like the temp.’”

When John August watched an initial edit of Go, he felt sick. “When you talk to screenwriters, the first time you see your first cut of your first movie, you do just want to kill yourself,” he says. “It’s just like, nothing works the way you wanted it to work.”

Unfortunately the studio felt similarly, and even recommended cutting the middle Las Vegas sequence. But the movie did surprisingly well at a test screening in the San Fernando Valley. The crowd even said that the Las Vegas segment was their favorite.

Still, the production would need reshoots to fix the problems, which included having all the segments essentially begin with the same starting point—Simon giving his supermarket shift to Ronna. They also altered the ending so that Simon brings a comedic climax to Claire and the drug dealer Todd Gaines’s arc, which was originally far more violent.

As they continued editing, and as test-screening responses got even better, the film began to cohere. “Some of the most interesting editing I was doing in that movie was because Doug had no idea how to transition from one thing to the next, or he just forgot to get coverage of something,” says Mirrione. “We just had to be like, ‘OK, this is the intention, this is what we want to do. How can I just repurpose five different things and make something?’ For me, the palette of how to do that became the culture. The rave culture, the remix DJ culture, where you’re taking all this stuff and ripping it apart and deconstructing it, putting it back together in a different way. That was partly born out of the necessity of us just not knowing how to plan well enough ahead.” (Mirrione says he began working with Steven Soderbergh after the director saw Go. They’ve since collaborated on nine films together, including the Ocean’s Eleven trilogy. Mirrione won an Oscar in 2001 for his editing on Traffic.)

Sony decided to premiere Go at Sundance in January 1999, which was vindication for Liman since the festival had rejected Swingers. With 15 relatives and 10 friends coming in for the showing, he learned he’d get only four tickets to the screening. Ever ingenious, he proposed that instead of the normal black hand stamps that audience members get when they turned in their ticket, they should have special flourescent Go stamps to align with the film’s rave theme. When the festival said the theater would need two of the special hand stampers, he ordered three and then stamped all his guests’ hands at dinner before they went to the movie.

The Sundance reception created anticipation for the film’s April release. When it hit theaters, critics were enthusiastic. In an A-rated review in Entertainment Weekly, Owen Gleiberman wrote, “Go is a rave-generation joyride, a kind of junior Pulp Fiction that courses along on waves of freedom and excitement. For all that, there’s a ticklish intimacy to its tone.” Still, it disappointed at the box office, bringing in just under $17 million.

“I think that the audience was in the middle of changing its moviegoing habits,” says Strauss. “It wasn’t a broad, mainstream, bawdy comedy like others that had been successful during that late-’90s time. It was distinctive, and sometimes distinctive movies take time to get discovered. But it’s always been successful to me.”

Though August has gone on to an accomplished career writing commercial films, Go was something different. He’d wanted to create something about young people who didn’t learn anything or weren’t severely affected by their mistakes. “Movies about this age are always like, ‘That’s the night that everything changed,’” he says. “I wanted to go against that trope.”

The movie ends with Mannie, who has just survived an overdose, asking his friends Ronna and Claire what their plans are for New Year’s. And for all of Liman’s talk about picking Go because it was his last chance to make an antiestablishment film, he’s spent the past two decades confounding, and often frustrating, Hollywood with his distinctly unbridled approach to moviemaking, with routinely bigger financial stakes.

“Like the characters in Go who didn’t really grow up by the end of it, I made Bourne Identity afterward and if you talk to the people who worked on that movie, they wouldn’t think that I learned some lesson about, ‘Now he has to play by the rules,’” Liman says. “I think the emotional experience of making Go wasn’t necessarily followed entirely by quote-unquote growing up. But it was the last time I didn’t have to be self-conscious about being rebellious.”

Eric Ducker is a writer and editor in Los Angeles.

Eric Ducker