Bill Murray was recently a guest on The Howard Stern Show on SiriusXM and revealed one major regret from his career. He had the opportunity to work with Clint Eastwood and didn’t take the part.
“Have you ever watched a film and said I want to act with this guy so bad?,” Stern asked (per The Hollywood Reporter).
Videos by PopCulture.com
Murray replied, “A long time ago, I was watching the Clint Eastwood movies of the day like Thunderbolt and Lightfoot or whatever the hell the movies he was making then, and I thought his sidekick gets killed and he avenges, but the sidekick gets a great part, a great death scene, I was like ‘I got to call this guy.’”
Murray wound up calling Eastwood who then asked the actor, “Would you ever want to do another service comedy?” Murray had just appeared in the military comedy, Stripes. In order to avoid typecasting he passed on the part.

Murray told Stern it is one of the few regrets he has in his career and that he apologizes to Eastwood every time he sees him. Murray mentions in the interview that it would have been a large-scale World War II movie, likely making it 1986’s Heartbreak Ridge, which Eastwood directed and starred in.