He received five Emmy nominations for Cheers and won once, in 1989, for Outstanding Supporting Actor in a Comedy Series. The show ran until 1993, by which point Harrelson was one of the most recognizable faces on American television and had begun the transition into film that would define the next phase of his career.
The film career that Cheers enabled was, from the beginning, distinguished by its resistance to the obvious. His first film, Wildcats (1986), was a Goldie Hawn sports comedy in which he appeared in a supporting role. By the early 1990s he had found the register that would mark his film work for the next three decades: a willingness to inhabit characters who existed at the margins or outside the lines of conventional moral legibility, played with a physical energy and a psychological specificity that made those characters compelling rather than simply transgressive.
## From Woody Boyd to Oliver Stone
The transition from Cheers to serious film work was not instantaneous, but it was deliberate. White Men Can’t Jump (1992) was his first film starring role, opposite Wesley Snipes in Ron Shelton’s basketball comedy-drama — a film that required Harrelson to play a hustler, someone who performs weakness to extract money from people whose assessment of his abilities is incorrect. The character, Billy Hoyle, is a white man who uses his opponents’ racial assumptions as the misdirection for his actual skill. It was a role that required both athletic competence and the specific kind of intelligent self-presentation that Harrelson had been developing since Cheers.