Bill Murray recently revealed to Howard Stern that one of his few career regrets stems from turning down a film opportunity with Clint Eastwood. The former Saturday Night Live star expressed that a fear of being typecast led him to decline the project.

"I was watching Eastwood's films of that era, such as Thunderbolt and Lightfoot, and I noticed a pattern where the sidekick often had a memorable death scene," Murray recounted in the interview.

Fresh from the success of the 1981 comedy Stripes, Murray decided to contact Eastwood directly to express his interest in working together.

"I called him out of the blue, and he asked if I would be interested in another military comedy, given my recent role in Stripes. He had a grand concept for a Navy-themed film," Murray explained. He further added that the phrase 'another military comedy' made him hesitate. "I wondered, ‘Would I become like Abbott and Costello?’ I had to do, like, military movies? And I said, ‘Well, God, I guess maybe I shouldn’t.’”

Several years later, Eastwood released the war drama Heartbreak Ridge, in which he portrayed Marine Gunnery Sergeant Tom Highway. “It’s one of the few regrets I have that I didn’t do it. Because it was a big-scale thing, and I would have gotten a great – I don’t know if I’d have gotten a great death scene; it was more of a comedy, that one – but it was great,” Murray said. “He had access to World War II boats, and he could have, like, made a flotilla and stuff, and there was some cool stuff in it.”

He added, ‘When I see him, I’m like, “I’m sorry; I wish I’d done that, Clint. I’m really sorry.’ He’s certainly well over it. He’s a very resilient fella.”

Stern then mentioned that Stripes was initially written for Cheech and Chong, but their agent passed on the project. Murray acknowledged that they would have brought a unique energy to it, given the stoner humour. With Ivan Reitman directing and Murray starring alongside John Candy, Stripes became a significant box office success, ranking as the fifth-highest-grossing film of its year.