Last month, the first picture emerged of Woody Harrelson in HBO’s The White House Plumbers, the upcoming limited series in which Harrelson plays Watergate conspirator E. Howard Hunt. The photo isn’t much to go on, really. Harrelson’s wearing a three-piece suit, which I guess you could argue captures some of the bureaucratic, buttoned-down anonymity that allowed Hunt to move through the shadows of American intelligence. But it certainly doesn’t leap out at you like Justin Theroux’s three-pound mustache for his role as G. Gordon Liddy. Woody just looks like Woody. 

You could say the same thing about Harrelson in the recent trailer for Venom: Let There Be Carnage. When he’s not morphing into a snarling, blood-and-sinew monster, Cletus Kasady/Carnage looks and sounds a lot like Woody too, his usual laid-back stoner’s lilt softened into a creepy singsong. 

It’s not that Harrelson doesn’t have range. In fact, he’s one of our most versatile actors, capable of playing manic psychopaths, existentially weary lawmen, and amiable eccentrics with equal conviction. If Harrelson never quite “disappears” into a role like, say, Christian Bale or Daniel Day-Lewis, he manages to perform the equally vital trick of making his myriad characters feel like natural extensions of the same man. With apologies to Walt Whitman, he is Woody, and he contains multitudes.

This wasn’t always so apparent. Harrelson arrived onscreen playing “the cute idiot” and seemed destined to stay there. With Harrelson’s breakout role as Cheers’s Woody Boyd, it was like he was barely acting: Woody Boyd hailed from Hanover, Indiana, where Harrelson went to college. Both Woodys were corn-fed church boys, radiating a sweet stupidity and a charming naivete about their own sex appeal. Harrelson even occasionally lapsed into the Midland twang of his childhood during Woody Boyd’s most egregious, “country rube” moments. The two seemed as synonymous as their names.

For years, Harrelson’s forays into movies were both aided and haunted by Woody Boyd. Being the nonthreatening patsy was the entire conceit of 1992’s White Men Can’t Jump. The guise allows Harrelson’s street-ball hustler to get the drop on Wesley Snipes and so many others. It also adds a layer of lovability to a character who is, really, kind of a selfish dirtbag. 

Thanks to Harrelson’s man-child innocence, he seemed far less believable—or sympathetic—as the tormented young architect who loses Demi Moore to Robert Redford in 1993’s Indecent Proposal. In the words of one particularly harsh critic, “Architect? You wouldn’t trust this boy to find an outhouse, much less design one.”

Subverting that expectation appealed to director Oliver Stone, who cast Harrelson as a serial murderer in 1994’s Natural Born Killers because, as Stone explains in Matt Zoller Seitz’s The Oliver Stone Experience, he had a “Kentucky or white trash” kind of vibe. Harrelson exorcised the specter of Woody Boyd by shaving off his floppy man-boy hair and lacing his amiable drawl with seduction and malice. It’s the kind of showy, scorched-earth role that practically screams for an actor to be taken seriously—and suddenly, many people did. 

Still, it wasn’t until 1996 that Woody fully escaped “Woody,” and became the kind of actor you could comfortably cast in just about anything. That year, over the span of six months, Harrelson delivered two wildly disparate performances that made him a full-blown movie star, laying the groundwork for everything that has followed.

In July 1996, Harrelson starred in Kingpin alongside his friend and fellow Texan Randy Quaid. Directed by Peter and Bobby Farrelly as the follow-up to their smash hit Dumb and Dumber, the comedy bears a lot of their hallmarks: road trips; gross-out gags about toilets and horny old ladies; physical trauma. But the film’s true wild card—not counting Bill Murray’s gloriously peacocking turn as “Big Ern” McCracken—is Harrelson’s beaten-down protagonist, Roy Munson. He’s a former bowling star who’s gone to seed, a self-pitying drunk with a prosthetic hand and a pathetic comb-over who latches onto Quaid’s Amish naïf, Ishmael, as his meal ticket. We’re meant to laugh at what a loser Munson is—his very name has become shorthand for blowing it—as a way of pardoning Munson for exploiting Ishmael for money and vicarious glory. 

However, Munson is more than just a sleazy, Jim Beam–swilling caricature. Harrelson plays him with real sympathy, grounding the character in a quiet sadness that balances out the more cartoonish moments (like a fistfight with Vanessa Angel’s breasts). The role was originally meant for Michael Keaton, and Keaton can certainly do crying-on-the-inside clowns, too. But it’s Harrelson’s aura of lost boyishness, eroded by so many years of cruel circumstance, that imbues Munson with pathos. It’s hard to imagine another actor taking on a scene like Munson’s return to his hometown without making it feel slightly stagey, rather than naturalistic and understated as Harrelson does. 

Kingpin was a box-office hit that year, though it was far from a critical one. Those kinds of accolades would finally arrive in the fall of 1996, when Harrelson starred in The People vs. Larry Flynt, Miloš Forman’s biopic about the founder of Hustler. You could argue that Harrelson was being typecast again. Flynt was more Kentucky trash, a moonshiner’s son turned scuzzy strip-club owner who only saved himself from being munsoned by publishing nude photos of Jackie Kennedy Onassis. But, as in Kingpin, Harrelson finds subtle dimensions to this self-proclaimed “scumbag.” He turns Flynt into someone you could root for, even if you find him repulsive.

The People vs. Larry Flynt racked up various awards and earned Harrelson his first-ever Academy Award nomination, though Harrelson was slightly overshadowed by Courtney Love’s surprise bravura performance as Flynt’s doomed, drug-addicted wife. Harrelson deftly landed all the Oscar-bait beats: the gunshot that leaves Flynt in a wheelchair; Flynt’s late-stage conversion to Christianity; all those scenes that see Harrelson’s gravelly voice raised to a Jimmy Stewart–esque tremble as he defends his God-given right to be a pervert. The film proved Woody Harrelson was not some country-fried himbo, but an actor who could take on the full, tragic span of a man’s life.

Do Kingpin or The People vs. Larry Flynt rate as Harrelson’s best movies? Not even close. But they were arguably the most important for his career. Starring in a hit summer comedy and an Oscar-nominated biopic within the same year raised Harrelson’s profile, marking his official arrival as a genuine, cross-genre movie star. Never again would anybody blink at Harrelson taking on any kind of role—just look at the ones he has coming up.

Besides The White House Plumbers and Venom: Let There Be Carnage, the next couple of years will see Harrelson play an assassin in the Kevin Hart buddy comedy The Man from Toronto, a Marxist yacht captain in Triangle of Sadness, and a doctor tending to Nazi leader Heinrich Himmler in The Man with the Miraculous Hands. In all of these movies, Woody will look and (with the exception of the Nazi one) probably even sound an awful lot like Woody. But as Harrelson first showed us back in 1996, there are a lot of him in there.