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From “Cheers” To “Han Solo”: Inside The Singular Career of Woody Harrelson, Underrated Superstar

A 30-year career and he’s hotter than ever. Fast Company talked to Woody Harrelson about Wilson, Han Solo, the past and the future.

From “Cheers” To “Han Solo”: Inside The Singular Career of Woody Harrelson, Underrated Superstar
Woody Harrelson in Wilson [Photo: Kimberly Simms, courtesy of Fox Searchlight Pictures] [Photo: Kimberly Simms, courtesy of Fox Searchlight Pictures]

Lucky breaks are common. Nobody is as lucky as Woody Harrelson thinks he is, though. He thinks he lucked out with White Men Can’t Jump. He thinks fortune favored Zombieland, the ultra-rare zom-com smash. And he attributes the zeitgeist-snatching mojo of True Detective to kismet. But when you’ve hit the jackpot as many times as Woody Harrelson has, clearly it’s not because of hot dice—it’s the person holding them.

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Wilson, 2017 [Photo: Kimberly Simms, courtesy of Fox Searchlight Pictures]

Woody Harrelson’s career is singular. Go ahead and try to find a point of comparison–it’s a waste of time. He has survived three decades and counting of the Hollywood meat grinder, only to continue ascending ever-skyward, like an MC Escher staircase, to the present, where he is more in demand and more reliable than ever. Stick Woody Harrelson in any kind of movie and he will only improve it. Now You See Me 2? He will play a magician with an evil twin (also a magician) and fully steal the show like David Copperfield stealing the Statue of Liberty. Edge of Seventeen? He will play the world-weary suburban school teacher and he will turn every cliche associated with that role on its head. And those are just two of the four films he appeared in last year. He will be in at least five more in 2017, which means there’s a chance he’ll star in more great movies this year than his fellow former cast members of Cheers will see. And the strangest part of all? He may just be getting started.

On the occasion of one of those films’s release, the unapologetically unusual Wilson, Fast Company walked through 30+ years with the underrated superstar, to give each phase of his unicorn career its due.

Cheers [Photo: Courtesy of NBCU Photobank]

Rising (1985-1992)

Auditions can make or break actors on any given day. When Harrelson aced one for what became his first signature role, Woody Boyd on Cheers, it was because he didn’t care much whether he got it or not.

“I had in my mind that I wouldn’t do TV,” Harrelson says, “because it ain’t like now, obviously. Like, now television is just phenomenal. But back then, I always looked at it as a little bit lowbrow. But then of course when I watched Cheers, I was like, well, this is high quality.”

He’d just been through a skull-rattling Broadway audition with much higher stakes. The struggling New York theater actor had made a deal with himself that if he didn’t book the part he was up for in Neil Simon’s Biloxi Blues, he’d fly home to Midland, Texas, having given acting his best shot. He’d booked a ticket and everything. Luckily, it never came to that.

“I was interested in Cheers, but I also knew that I was doing something on Broadway, so I was absolutely carefree in that audition,” Harrelson says. “‘You don’t want me? Fine. I’m gonna go do my dream on Broadway.'”

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For eight years, Harrelson slung suds behind the bar at Cheers as the dimwitted, big-hearted Woody Boyd, whom the show’s creators named after him. He managed to stand out in a stacked cast, winning an Emmy for the role in 1989, but he was only giving America a limited view of his capabilities. One of Harrelson’s talents is that he’s an intellectual chameleon. He can play the smartest guy in the room, or the dumbest, or the smartest pretending to be the dumbest—and he can tip viewers off to which he is with one wily-eyed look. Woody Boyd offered him the opportunity to fingerpaint in only a few shades, and for a long time those seemed like the only shades Hollywood wanted him to use.

“I liked playing Woody Boyd, but I didn’t want that to be my only foray into the entertainment world,” he says. “That was the case for like six years until I got White Men Can’t Jump.”

Although he’d made other films before, including Wildcats with Goldie Hawn and future costar Wesley Snipes, White Men Can’t Jump was the first one he’d had a lead in, and the first hit. It was the kind of movie destined to air on TBS every Sunday afternoon in perpetuity, and it was good enough to make you want to watch the whole thing every time you flipped by and saw it on. White Men Can’t Jump was a catchphrse-coining, barbed buddy comedy laced with drama and romance, and it immediately created more than a half-court of buffer space between Woody Harrelson and Woody Boyd.

White Men Can’t Jump, 1992[Photo: courtesy of 20th Century Fox]

Diversification (1993-1998)

The next stage of Harrelson’s career was marked by a further diffusing of his on-screen persona. Over five years, he would star in an erotic drama, a social satire about serial killers, a prestige biopic, and a not-insignificant number of goofy comedies—and he would end up with his first Oscar nomination.

“It wasn’t that I was so determined to branch out from comedy,” he says. “Hell, I still feel like I don’t want to branch out from comedy. But, I don’t know, these things come along and you gotta do them.”

Indecent Proposal was up first, a sexy morality play that had couples around the world arguing about whether they’d let an interloper into their marriage for one night if it meant a million-dollar payout. It was the second big-impact cultural hit in a row. He was on a roll. The following year, however, he made a film with less enviable reverberations. Harrelson dove deep into his personal demons—and those of his father, an actual convicted murderer—to play one of the titular roles in Oliver Stone’s Natural Born Killers. He was shockingly convincing. The controversial film (scripted by Quentin Tarantino) reportedly inspired several real-life murders.

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It was around this time, though, that Harrelson started cultivating a skill that would become a hallmark of his career: creative collaboration. He and Wesley Snipes had improvised lots of dialogue in White Men Can’t Jump, and he had even more ideas for the character Mickey in Natural Born Killers, including the recurring motif of the shadow.

“I believe as an actor, you want to not just be hitting your mark and saying your line,” Harrelson says. “If possible, you want to add something to it, add something to the whole story.”

He had a lot to add when it came to one of his next films, 1996’s The People vs Larry Flynt, in which Harrelson played the much-loathed real-life founder of Hustler Magazine. It was the opposite of White Men Can’t Jump, a drama with comedic elements, and it would require him to do things he’d never done onscreen before. (Again.) Part of preparing for the part meant preparing the part for him.

“[Director] Milos [Foreman] was real open to stuff. I did a whole reworking of that script before we shot it,” Harrelson says. “Because I’d just been working back to back to back and I was trying to get it pushed to where we didn’t have to start it right away in January. So, I flew to where Larry [Flynt] was vacationing at this island and we worked on it, went through the whole freaking script, and then called Milos. Spur of the moment, he came out, God bless him. And then we worked on it and Ed [Norton] came out too.”

The resulting film earned Harrelson an Oscar nomination. It was only three years after Cheers had gone off the air, and already he’d laid the groundwork so that it didn’t seem odd for the guy who played Woody Boyd to be an award season contender. What should have been a victory lap, though, turned into practically a walk of shame. The well-reviewed film was a box office bomb, at least partially due to Larry Flynt being the kind of notorious that attracts serious resistance. It was one of those instances that disproves the maxim ‘all publicity is good publicity.’

“That whole Larry Flynt thing took a bad turn,” Harrelson says. “It was actually a low time in my career. Even though I was nominated, there was a campaign against it, so that hurt it and I think hurt my career too.”

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The next couple years included a chance to act for then-elusive director Terrence Malick in The Thin Red Line, but not many other major opportunities. Harrelson had branched out and he’d broken through, but he didn’t like what he found on the other side.

The People vs. Larry Flynt, 1996 [Photo: courtesy of Columbia Pictures]

Exile (1999-2006)

For roughly the length of the Bush administration, give or take a year, Woody Harrelson was in the wilderness. He appeared in a few decent indie films and a handful of flagrant flops (Play It To The Bone, EdTV, She Hate Me, A Prairie Home Companion). There were four years where he didn’t make any movies at all.

“I wanted to take some time off and I found I really liked taking time off so I took a lot,” Harrelson says. “I wasn’t enjoying what I was doing and I was overdoing it. I was working too many hours, too many back-to-backs to the point where I wasn’t enjoying my life. And I wanted to just take time off.” He waits a beat, as if weighing whether this version of events is accurate and then adds a note. “This also coincided with a time where I was probably a little less in demand, so that worked out well.”

Although Harrelson didn’t exactly become unfamous during this time in the cinematic hinterlands, his track record was undeniably diminished. Or at least it seemed that way at the time.

The Messenger, 2009 [Photo: courtesy of Oscilloscope Laboratories]

Experimentation (2007-2011)

The film that brought Harrelson back to civilization, so to speak, was No Country for Old Men in 2007. Years of cameos in the likes of Anger Management and guest turns on Will and Grace had made audiences forget what a subtle, layered Woody Harrelson performance looked like, and how he could sink his teeth into a substantive role. Something about appearing in a beloved and Academy-honored movie again revived a hunger in Harrelson, because afterward he was officially back from sabbatical. The next few years were marked by an uptick in productivity and a wider array of roles and films.

Although he’d already proven he had range, Harrelson suddenly became more eclectic than ever in his choices. He tried out experimental indies, broad Will Ferrell sports comedies, big-budget disaster flicks, the aforementioned Zombieland, and a metaphysical misfire with Will Smith.

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“When I didn’t listen to my agents, things didn’t go so good,” Harrelson admits. If he was intrigued by a director, though, he was willing to take a leap of faith. “The key thing is the director. I mean, script is obviously very crucial, because you could have a great director and a shitty script and it’s not going to turn out great, but I’m more focused on directors than anything. Oren Moverman was a first time director and I did two movies with him. I think he’s phenomenal. On the other hand, not a lot of people saw the movies we did together, but I really loved working with him.”

One of those movies with Oren Moverman, The Messenger, a harrowing stateside drama about the Iraq War, earned Harrelson his second Academy Award nomination. He did not win, but the renewed sheen of wide acclaim set the stage for what was to come in the next couple years.

The Hunger Games, 2012 [Photo: Murray Close, Courtesy of Lionsgate Films]

Ascension (2012 – ?)

Because Woody Harrelson and Matthew McConaughey are good friends who’ve worked together many times, they’re often discussed in tandem. But while much was made of the “McConnaissance” that led up to HBO’s critically adored first season of True Detective in 2014, nobody was really talking about the “Harrelscension.” Perhaps it’s because McConaughey was coming out of a foggy period of interchangeable romantic comedies when he began devouring meaty artistic roles, while Harrelson was merely becoming more commercially viable than he’d been in some time. In any case, Harrelson’s Emmy-nominated performance in the HBO political comedy, Game Change, hit around the same time he got swept into the massive blockbuster Hunger Games series, and Now You See Me quietly made well over a quarter-billion dollars disappear. Although he’d never really gone away, Harrelson was now indelibly back.

“It’s definitely a different thing,” he says of his post-Hunger Games level of fame. “I’ve gotten to know another generation and vice versa.”

The four-film series offered the kind of job security that allowed Harrelson to take an artistic risk with True Detective, a promising neo-noir overseen by an unproven talent, Nic Pizzolatto, and which required a grueling six-month shoot in Louisiana.

“Only two of the eight episodes were written when I first saw the script, and they were really good,” Harrelson says, “although I thought my part was not great. But you know, we worked on that to make it better.”

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In the first few months of 2014, True Detective became the kind of pop culture entity you felt left out if you hadn’t seen. Theories about the Yellow King’s identity percolated throughout the internet and ratings were high. Although none of the Emmys the show brought in went to Harrelson, True Detective was a bravura acting showcase for him, which was not lost on anyone. The limited series paved the way for a 2017 that consists of an elegant mix of genres, styles, and budgets.

First up is Wilson, an adaptation of a Daniel Clowes graphic novel featuring Harrelson as the world’s most curmudgeonly people person. Next is Three Billboards Outside Ebbing, Missouri, a Coen Brothers-style yarn directed by Martin McDonagh, whose profanity-heavy trailer was the talk of Twitter when it was released last week. Over the summer, he’ll play the lead human in War for the Planet of the Apes, and then in the fall he’ll co-star in high-profile literary adaptation The Glass Castle with Brie Larson. At some point, we’ll also be seeing one of the two political films he recently shot with Rob Reiner–possibly the one in which he plays former president Lyndon B. Johnson. Oh yeah, and in 2018, he has a big part in the next Star Wars spin-off anthology movie, where he may play the young Han Solo’s mentor or father, but which he definitely cannot tell Fast Company much about at all. It’s the kind of year one might’ve expected him to have after his initial winning streak in the ’90s. Better late than never.

What will the next stage of Harrelson’s career look like? Perhaps he’s about to enter his auteur phase. Earlier this year, he executed a historic feat when he directed the world’s first “live movie,” Lost in London, from a script he’d written. If the words “live movie” sound an awful lot like “play,” consider that this play had 14 separate locations, involved 30 actors and 24 sound people, and was live-streamed into movie theaters.

“I had that script lying around a long time and I finally felt like, well, if I don’t get on this thing now, then I’m just going to keep working on these other projects and I’m never gonna do it,” Harrelson says. “The whole idea was the convergence or the merging of theater and film. It was a massive undertaking and we rehearsed for about six or seven weeks. It nearly killed me, but I’m glad how it turned out.”

The original idea was to distribute the finished film on iTunes, but Harrelson is now rethinking it, and talking with Picture House to distribute it in a limited release. In the meantime, he’s also finishing up writing another film, a slapstick comedy called Fitz about a guy named Fitzgerald Fitzsimmons (“An Irish guy,” Woody clarifies, deadpan.) He’s currently about three-quarters satisfied with the draft he has, and is confident about moving forward with it. Beyond that film and Han Solo, his hopes for the future are pretty simple.

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“The other day I re-read an old play I’d written, and it’s terrible but it has the potential to be really interesting,” he says. “I wanna get some great theater director to direct it and I’d like to get back on the boards, do a comedy that’s gonna be like ninety minutes, make the audience feel good, make the actors feel good, and then get to the pub.”

Who knows, maybe he’ll get lucky.