Bill Murray Says There’s One Director He Wishes He Had Worked With: ‘It’s One of the Few Regrets I Have’

Bill Murray Few Regrets

Bill Murray, the legendary comedian who once shone on “Saturday Night Live,” has frequently underscored that if he were to relive certain episodes of his career, only the very few of them would make him seriously ponder whether he had made the right decisions. On giving thought to his past, one of the instances that Murray deeply regrets is the one where he retreated from his decision to join Eastwood in a project. He mentioned to Howard Stern that a potential collaboration with Clint Eastwood was thrown his way but by the reason of his career’s worrying he had no option but to reject it.

Bill Murray, while chatting with Stern, recollected the moment he turned down a project which would have had him acting with Clint Eastwood. As a matter of truth, however, he insinuated that he perhaps let the idea stay away from the pursuit because he was afraid of the risk of being typecast in one role. He went on to describe that Clint Eastwood’s movies of that period involved a partner or a sidekick. He was captivated by how those characters got outstanding scenes in Eastwood’s films, particularly when they went out in dramatic or poignant ways.

In those days, Murray was watching Eastwood’s popular titles, mentioning “Thunderbolt and Lightfoot” among others. Observing how the sidekick would inevitably meet a tragic end, he imagined that position might be a creative goldmine for an actor who wanted to deliver an unforgettable performance. The idea of playing a person who dies in such a vivid way on screen was intriguing, especially given the captivating way Eastwood would eventually avenge that character. Yet Murray found himself wrestling with the implications of committing to a role like that, wondering whether it might affect what offers came his way afterward.

The Timely Phone Call

Meanwhile, Murray had just wrapped up filming “Stripes” in 1981. That comedy had turned out to be a significant success, catapulting his reputation in Hollywood to new heights. Motivated by this recent triumph, he felt a strong urge to reach out directly to Clint Eastwood. He picked up the phone and shared how much he wanted to be part of one of Eastwood’s next endeavors, thinking it could lead to an exciting collaboration. The conversation, though promising at first, soon presented a twist that made Murray hesitate and question if he should actually commit to what Eastwood proposed.

Once Murray and Eastwood were on the line, Murray recalled that Eastwood pitched an enormous Navy-themed comedy, fully aware that Murray had just finished a military-focused movie. Eastwood asked if he would be interested in tackling another story set in the military, hoping to harness that similar energetic style. This, however, triggered Murray’s anxiety about being pigeonholed. He worried that if he accepted another service-related role so soon after “Stripes,” he might end up forever recognized as the actor who only did military comedies. At that moment, he envisioned a future of endless uniformed roles, maybe transforming him into an Abbott-and-Costello-like figure stuck in repeating formulas.

A Later War Film

Under the weight of that concern, Murray turned down Clint Eastwood’s generous offer. Though his career went on to feature countless iconic characters and award-winning performances, he still finds himself reflecting on the path he did not take. In interviews, he has hinted that this was a decision guided by fear—fear of typecasting and fear of an uncertain comedic rut. Even so, there remains a trace of wistfulness every time he mentions how close he came to sharing the screen with one of Hollywood’s most legendary stars.

Several years after Bill Murray passed on a potential collaboration with Clint Eastwood, the celebrated actor and director went on to create the war movie “Heartbreak Ridge.” In that film, Eastwood portrayed the no-nonsense Marine Gunnery Sergeant Tom Highway, who led a group of undisciplined recruits through rigorous training. Although this production came along some time after the initial idea Murray had discussed with Eastwood, it served as a glaring reminder of the large-scale military story Murray did not get around to doing. Moreover, it showcased Eastwood’s knack for creating tough but human characters, especially in a setting where camaraderie and discipline intersect.

Yet, Murray has repeatedly declared that “Heartbreak Ridge” itself was not the exact film he turned down; he merely feels that this later movie shows what an Eastwood-led war project might look like. He emphasized in an interview how his original conversation with Eastwood would have involved a comedic take on military life—something that, ironically, aligned with much of Murray’s comedic persona at the time. The scale of the possible collaboration was what truly got him excited, because Eastwood had extensive access to World War II naval vessels and could stage a dramatic show of force on the water.

Lingering Thoughts

Looking back, Murray admits that not working on Eastwood’s big war-themed concept remains one of the scarce regrets he holds. He wonders if he might have enjoyed an especially memorable on-screen exit scene, although he also acknowledges that Eastwood’s notion seemed more comedic in tone, so maybe a grand death moment would not have been on the table. Nonetheless, he sees that big opportunity as something that slipped away due to a mixture of timing and hesitation. Over the years, he has stressed that this decision continues to cross his mind whenever he reflects on the diverse roles he could have explored during his earlier career.

Significantly, Bill Murray believes Eastwood would have been a generous collaborator, given the resources and connections he brought to the project. The chance to handle large-scale naval sequences and assemble a genuine flotilla remains, in Murray’s eyes, an exciting and unique proposition. Even though Murray has acquired plenty of accolades and worked with a broad range of directors, he still laments skipping that creative avenue. He claims that each time he runs into Eastwood, he offers an earnest apology for letting the idea pass him by. Interestingly, Murray notes that Eastwood appears unfazed, describing him as “a very resilient fella” who presumably moved on the moment Murray said no.

A Friendly Apology

During interviews, Murray has openly shared this regret, stating that he cannot help but bring it up when he meets Eastwood in person. He confesses to telling him, “I’m sorry, I wish I’d done that, Clint, I’m really sorry,” suggesting that the opportunity to join forces with the legend remains a nagging thought. Even so, Eastwood’s adaptable nature and focus on forward momentum make it clear that he harbors no disappointment. For Eastwood, it appears to be just one fleeting possibility among his many cinematic accomplishments.

Murray’s openness about this slight remorse reveals that even the most successful entertainers occasionally look back and realize they might have made different decisions. Yet he seems grateful that he can at least speak candidly with Eastwood, offering a direct acknowledgment of what could have been. This friendly candor serves as a testament to the mutual respect they share.

Meanwhile, radio host Howard Stern pointed out another surprising fact: “Stripes,” which became a breakout hit for Murray, did not begin its life with him in mind. Instead, it was initially written for the irreverent comedic duo Cheech and Chong. However, the duo’s agent decided it was not the right project for them. Murray has suggested that both Cheech and Chong might have fit seamlessly into the film’s stoner-themed sequences, which featured carefree, freewheeling humor. Yet circumstances shifted, allowing director Ivan Reitman to cast Murray and John Candy instead. That switch altered the film’s comedic style and helped cement its place in pop culture.

Unexpected Comedy Roots

Murray believes that if Cheech and Chong had accepted the original offer, they would have discovered plenty of opportunities to indulge their trademark comedic style, elevating the movie’s stoner appeal. Even so, Murray’s involvement brought an entirely new tone to the film, blending the comedic approach he had honed on “Saturday Night Live” with a storyline that included military boot camp hijinks. The final product struck a chord with viewers, proving that unexpected casting choices sometimes lead to a delightful surprise.

Thanks to the persuasive guidance of Ivan Reitman, “Stripes” evolved into a resounding box office triumph. Viewers flocked to see the combination of Murray’s sardonic humor and Candy’s lovable antics. In fact, the film wound up as the fifth-highest grossing release of its year, validating the decision to move forward without Cheech and Chong. The movie’s commercial performance also underscored the powerful draw of Murray’s comedic talent, which expanded well beyond his earlier television roots and reinforced his rising star status in Hollywood.

Ultimately, the runaway success of “Stripes” set Bill Murray on a path that would include a wide range of comedy, drama, and even some action-oriented films. Yet in spite of that extraordinary career trajectory, he still mentions the missed Eastwood venture whenever he contemplates the roles he did not take. He stands by his overall choices but admits that, given the chance to rewind time, he might have jumped at that unique blend of large-scale military spectacle and comedic flair. Even so, through his enduring success and his rare moments of regret, Murray shows that every path in Hollywood is marked by a mix of opportunity, caution, and the unpredictable nature of show business.