The 1987 role Woody Harrelson called his biggest regret: “One of the worst decisions of my life”

He’s worked with some of the biggest directors of their respective generations at various points throughout his career, but there’s only one behind-the-camera legend that Woody Harrelson stabbed in the back.

Unsurprisingly, torpedoing what would ultimately be a once-in-a-lifetime opportunity to collaborate with one of the most influential directors in modern Hollywood, in what was an unsuccessful attempt to further his own acting aspirations, backfired, and he’s regretted it ever since.

While he’s always come across as a laid-back, jovial, and generally carefree individual, that doesn’t mean Harrelson is a wallflower or a pushover. He hated Quentin Tarantino as a matter of principle for years, and his reputation hasn’t always been that of the easiest or most straightforward guy to work with.

Back in the 1980s, though, he was only at the beginning of his journey. He wasn’t an unknown, with Cheers premiering in September 1985 and nudging him toward household name status in his first major role, but his only feature to date was 1986’s Wildcats, and he fancied making a mark on the silver screen.

Unfortunately, the chance to do that coincided with a 1987 run of the play, A Woman of Mystery, at Los Angeles’ Court Theatre. Initially, it was a chance he seized with both hands, as you’d expect with a ‘New Hollywood’ pioneer and trailblazer running the show, but not enough to stop him from committing an unforgiveable betrayal.

“One of my biggest regrets was, I was doing a play in LA with John Cassavetes,” Harrelson recalled. “I had a full realisation of how amazing this guy was, although I didn’t understand in terms of his larger body of work and his influence on independent movies and so forth, but I didn’t understand that at the time.”

Still, working with Cassavetes was a big deal for a 20-something actor who wasn’t all that experienced in the grand scheme of things, but when a potential movie role came along, with the auditions being held in Rome, he betrayed the legendary filmmaker. “I left the play and flew over there,” he sighed. “I didn’t get the part. I could have come back, and he would have let me back in the play. I didn’t. I regret leaving it.”

Understandably, the three-time Academy Award nominee called it “one of the worst decisions of my life” and “one of my biggest regrets,” but not strictly on a professional level, either. Harrelson conceded that he “should have stuck by that guy,” and to abandon Cassavetes was “a real lack of integrity on my part.”

A Woman of Mystery was also the last completed stage or screen work of the auteur’s career before his death in 1989, and while he did get to be a part of it for a hot minute, Harrelson will always regret that he didn’t come back to the play after leaving Cassavetes high and try for the sake of a failed audition.

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