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Woody Harrelson’s Daring Rise to Stardom in the 1990s

Graduating from ‘Cheers’ to the big screen, he constantly tested the limits of what a leading man could look like

Welcome to Misleading Men, a regular feature where we look back at the actors who ruled Hollywood for one brief shining moment.

There are lots of reasons to be grateful to Keanu Reeves, but here’s another: In a very roundabout way, he’s responsible for Woody Harrelson having a film career. It probably would have happened anyway, but because of Reeves — specifically, something he couldn’t do — it happened sooner.  

In the early 1990s, Harrelson was on Cheers, the massively popular sitcom that was his first real break. He’d been so grateful to get the part as a young, struggling actor, but as is often the case with long-running TV shows, playing preternaturally dopey and idealistic Woody Boyd ended up being a bit of a double-edged sword. “You know, I was on Cheers for eight years, and I couldn’t get another job,” Harrelson once said in an interview with his good buddy Owen Wilson, “and I thought, ‘I’m going to be Woody Boyd forever.’ Which is not bad, but I really thought I was capable of more.”

The shift happened when he was up for Billy Hoyle, the trash-talking basketball hustler in writer-director Ron Shelton’s White Men Can’t Jump. After making Bull Durham, Shelton learned an important lesson — you had to really believe the actors could play the sport — so his auditions for White Men Can’t Jump involved pickup games. “I just threw a ball out there,” Shelton told Entertainment Weekly. “That sort of weeded it out. Agents would call asking about their clients and I’d say, ‘He can’t play. He can’t beat me, never mind these guys.’”

Reeves had been someone Shelton was interested in having play Billy, but he decided the Point Break heartthrob wasn’t a convincing baller. “I guess I probably would’ve just been Woody Boyd but for the fact that Keanu Reeves didn’t play great basketball,” Harrelson told Wilson. “That was the only thing that saved me.” (The other thing that may have saved him: His longtime pal Wesley Snipes, who he was friends with before they made White Men Can’t Jump together, bragged that he intentionally sabotaged Reeves during his audition by not giving him much to work off of as a scene partner: “[Reeves] would improvise and say something where there would be a natural response from me,” Snipes said back then, “and I just left him out there like dirty laundry.”) 

However it worked out, Harrelson and Snipes’ clear chemistry made White Men Can’t Jump work, helping Harrelson escape from being “just” a sitcom guy. As importantly, the film paved the way for a decade of really impressive, very different starring roles. Woody Harrelson has done a lot of great work since the end of the 1990s, becoming a vivid character actor and a welcome addition to blockbuster franchises. (He’s the villain in the upcoming Venom: Let There Be Carnage.) But Harrelson in the 1990s was really something because the era provided him with a chance to be a flat-out movie star. Now 60, he’s more exciting when he’s not smack-dab in the middle of a picture, when he’s doing something a little strange on the margins instead. But, of course, that was what was so cool about him in the 1990s: He was doing the exact same thing, but as the film’s main character. 

You can understand why Harrelson started to bristle a bit at being Woody Boyd. It’s a terrific character on a terrific show — he even won an Emmy — but if the most notable role on your acting résumé is that of a sweet dimwit, you might be worried that it’ll be the way the world always sees you. White Men Can’t Jump changed that impression: Billy Hoyle was a brash, foul-mouthed guy with a sexy girlfriend (Rosie Perez) in a grownup, R-rated film. The only thing that Boyd and Billy had in common was that they weren’t the brightest, and the film allowed him to show a sauver, cockier side. This new guise suited Harrelson. He sure looked like a leading man. 

In another universe, Harrelson would have gone from White Men Can’t Jump to Benny & Joon, where he and Laura Dern were set to play the film’s titular brother and sister. (Apparently at one point earlier in the casting, he was going to play opposite Susan Sarandon.) Johnny Depp, who portrayed Joon’s love interest, later said of his departed costars, “Laura Dern is great. And Woody Harrelson… well, I’ve never seen anything he’s done, but I’m sure he’s very good.” 

No matter: Harrelson had jumped to Indecent Proposal, where he once again showed audiences he wasn’t Woody Boyd. As David Murphy, an aspiring architect married to his childhood love Diana (Demi Moore), he got to be in a steamy drama — Fatal Attraction director Adrian Lyne always pays close attention to his film’s sex scenes — about a wealthy older man (Robert Redford) who promises to erase the couple’s debt if David will let him have one night with his wife. 

At the time, Indecent Proposal was a divisive, teasingly preposterous, button-pushing movie built around a watercooler what-if — Would you let some rich dude sleep with your girl for a million bucks? — that was criticized for its sexist premise. And yet, Harrelson did some interesting things as David, presenting straight male viewers with a nightmare scenario: Did my wife agree to this indecent proposal because we need the money, or because there’s something about this other guy that’s more appealing and manly than me? 

Ultimately, Indecent Proposal isn’t smart enough to really dissect its story’s gender power dynamics or class issues, but it took guts to play a seemingly decent husband who can’t face his wife after she returns to him — sure, he encouraged her to sleep with this guy, but now he’s mad at her because she did. It’s a very intriguing performance that communicates the deep-seated sexual and hunter-gatherer insecurities that a lot of men harbor. The whole film is about the fact that Woody Harrelson isn’t Robert Redford. 

Harrelson was up for all kinds of risks that decade. Next up was Natural Born Killers, which chronicled his Mickey Knox on a road trip of carnage with equally depraved wife Mallory (Juliette Lewis). I still find Oliver Stone’s satire of our ultraviolent society rather lame, but I don’t blame Harrelson. If anything, he and Lewis are so committed to their characters’ twisted love story that they bring a sincerity to the proceedings that Stone’s self-important style smothers. 

Controversial in a different way than Indecent Proposal, Natural Born Killers gets part of its power from Mickey and Mallory’s guileless evil — they exist in a lawless world where their devotion to one another is all that matters. In a strange way, it might be Harrelson’s most innocent character since Woody Boyd — albeit with a way higher body count. “I saw it as a misunderstood romantic comedy,” Harrelson later said of Natural Born Killers. “But if you’ve got to explain that something’s a satire, then I guess it don’t really work.”

Harrelson always swore it wasn’t his intention to be provocative. “I didn’t know [Natural Born Killers] would be that controversial,” the actor insisted. “It was very controversial. People are like, ‘Do you like doing controversial movies?’ I’m like, ‘Hell, no. I like doing movies people would go see, not movies people are boycotting.’” Still, he had to know what he was stepping into when he signed on to play Hustler mastermind Larry Flynt in The People vs. Larry Flynt — although, as with Mickey, there’s a disarming straightforwardness about the way he portrayed Flynt. The movie saw him less as a crude pornographer and, instead, as an enterprising American with a dream. 

“If I hadn’t liked him, I wouldn’t have played the part because when I was growing up in Texas and Ohio, he was very much what you would call vilified in the media,” Harrelson once said. “I don’t like the whole pornography thing, but I went and met him up at his offices over on Wilshire Boulevard, and I really liked him. A more candid fellow you will not meet.”

Harrelson’s attitude about porn may surprise people — especially considering what a politically outspoken liberal (and longtime pot defender) he’s been — but, in hindsight, the fact that he had to come around on Flynt probably helped give the performance its oomph. In the film, Flynt has a boyish brattiness to him, but Harrelson’s natural charm — the same charm he exuded as the sweet, lovable Woody Boyd — forced you to see him as a guy who deserved the same Constitutional protections afforded any other citizen. Even if The People vs. Larry Flynt scrubbed the man’s less-savory aspects, it reaffirmed Harrelson’s willingness to take chances with his stardom. For his trouble, he received his first Oscar nomination.

But if you thought that performance was nervy, imagine delivering it just a few months after you play a degenerate has-been bowler with a hook for a right hand because of a get-rich-quick scam that went awry.

For my money, Kingpin is still the Farrelly brothers’ funniest film, casting Harrelson as Roy Munson, and Randy Quaid as the Amish nitwit Ishmael who may be a bowling phenom. After a string of dramatic roles, Kingpin was a happy change of pace — plus, Harrelson got to play a real son of a bitch who, deep down, is a good person if he ever allowed himself to be. 

It just so happened that Harrelson had been friends with the filmmakers for years before Dumb & Dumber put them on the map. “We knew him before he even got the role on Cheers,” Bobby Farrelly said in 2016. “He was just one of the guys that we’d hang out with and play basketball. He was a funny guy and we were fast friends, and we’ve stayed friends ever since.” Unlike White Men Can’t Jump, though, Harrelson wasn’t a natural at the sport that was this film’s centerpiece. (“Woody was horrible,” Peter said in that same interview. “He was shockingly bad. Like, he never got better. … I don’t think Woody ever broke 100 the whole time we were bowling.”) 

Believability didn’t really matter with a broad comedy like Kingpin, though: Harrelson’s willingness to play a guy so pathetic — and yet also willing to turn his life around — was more important. As great as Bill Murray is in the movie as the hotheaded bowling champion Big Ern, Harrelson’s trickier role grounds Kingpin in something real and emotional, which only makes the crass humor and ridiculous slapstick all the more hilarious. If The People vs. Larry Flynt is the sort of prestige movie that serious stars pursue to prove their acting bona fides, Kingpin was a reminder that Harrelson couldn’t be pigeonholed. Lots of actors could have played Larry Flynt — I’m not sure many could have done justice to Roy Munson.

But even though he had a string of starring roles in the 1990s, his movies (with the exception of Indecent Proposal) were never big at the box office. And he wasn’t immune to flops. (His reunion with his buddy Snipes was in the dire Money Train, and nobody remembers The Cowboy Way.) Being a conventional movie star was probably never in the cards — if anything, it was amazing that he sustained it as long as he did. And after the pushback by feminists against The People vs. Larry Flynt, an outcome which Harrelson said “broke my heart,” the actor seemed to ease out of the limelight. He’s a noirish hoot in the sleazy, silly Palmetto alongside Elisabeth Shue, and he’s terrific in a very small part in Terrence Malick’s The Thin Red Line — he’s the soldier who blows himself up by mistake with a grenade — but it nonetheless felt like the end of a stellar run for Harrelson. No longer just a TV star, he was a respected actor. But superstardom wasn’t his destiny. Something else was waiting for him.

Harrelson has never really stopped working, but this century he hasn’t always had the kind of standout parts that could demonstrate his range. More often, he’s fluctuated between notable bit parts in acclaimed dramas like No Country for Old Men and hitching his wagon to hits such as Now You See Me, Zombieland and the Hunger Games films. It’s no disrespect to say that people probably didn’t flock to, say, 2012 because he was in it — but finding out that he’s in a blockbuster like that almost certainly increased your interest in seeing it. He’s the definition of the value-add — he doesn’t carry the movie, but you’re sure glad he’s there. In fact, it’s actually perfect that Harrelson and Owen Wilson are such buddies: They’re both guys who brighten a film by dint of some special, secret bond they have with the audience. We see them and we relax: Oh, okay, this’ll be good.

Sometimes, Harrelson can still really shine. He earned well-deserved Oscar nominations for The Messenger and Three Billboards Outside Ebbing, Missouri playing complicated men whom he imbued with a rumpled humanity. (And on the small screen, people loved him in True Detective.) Those performances are so assured, so effortless, that it can’t help but remind you that he used to star in movies where he’d play similarly difficult characters — that there was a Hollywood where such films could actually exist. 

Frankly, the fact that he’s still in big movies — but part of an ensemble, usually supporting the bigger star — is an odd commentary on the state of the film industry. There’s no point moaning about “They don’t make ‘em like they used to” — first of all, it’s a tired complaint, and second, it’s not true — but every time Harrelson is in a Solo or a Venom, it does feel like he’s playing a prank on all of us. Studios used to make movies other than ones like those — movies that needed a Woody Harrelson to be their star — but he’s not gonna stew about it. 

Still, anyone who remembers that 1990s run is always in on the joke with him. His string of ‘90s starring vehicles was a thing of beauty we all shared — more beautiful, in fact, because it wasn’t going to last.