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Bill Murray has had the chance to work with some great directors, but there’s one filmmaker he turned down that he now regrets saying no to. Murray was offered a part in Clint Eastwood’s war film “Heartbreak Ridge,” and he said no because he thought he would be typecast in service films like “Stripes.”

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The “Rushmore” star was on “The Howard Stern Show” when he said the kinds of movies Eastwood was making in the eighties appealed to him. In particular, he wanted to play one of Eastwood’s sidekicks: “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 like a great part, a great death scene.'”

Murray got in touch with Eastwood but didn’t like what he heard. “I was like, I got to call this guy,” Murray said. “So I called him out of the blue, and he said, ‘Would you ever want to do another service comedy?’ Because I just made ‘Stripes’ and he had this great idea for an enormous Navy thing. And when he said, ‘Would you ever want to do another service comedy,’ like jeez, ‘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.'”

The movie in question was 1986’s Oscar-nominated “Heartbreak Ridge,” and Murray said saying no to that is one of the only regrets he has left.

“It’s one of the few regrets I have is that I didn’t do it,” Murray said. “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.”

While for a long time Bill Murray was known mostly for his comedies, since the late nineties he’s gravitated toward more dramatic work, particularly in his collaborations with director Wes Anderson. In 2004 he was nominated for Best Actor for his work in “Lost in Translation,” losing to Sean Penn for “Mystic River.”

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