The actor who completely baffled Clint Eastwood: “It would look like you’re doing it for a paycheque”
Clint Eastwood has always been willing to take risks. He has often said he doesn’t like to repeat himself, so he will do whatever he can to try new things with each film. However, he’s also never been opposed to playing a character again if he feels there’s gas left in the tank. After all, in his 70-year career, Eastwood has made sequels to three of his films, two of which are arguably his most beloved characters. This is why it may have puzzled some fans when he took a shot at a fellow franchise mainstay at a point when that actor was reportedly contemplating returning to his most iconic role. In fact, Eastwood accused him of simply doing it for the paycheque.
When Eastwood sat down with The New Yorker in 2003, he had just started production on Mystic River, a Boston crime drama that would become one of his most acclaimed directorial efforts. It was nominated for six Academy Awards, including ‘Best Picture’ and ‘Best Director’ for Eastwood, with stars Sean Penn and Tim Robbins taking home the trophies for ‘Best Actor’ and ‘Best Supporting Actor’. It was vindication for Eastwood, who had spent the years before directing middling efforts like True Crime, Space Cowboys, and Blood Work.
As he discussed the film with Ross, though, Eastwood began talking about the realities of Hollywood in the early 2000s. Perhaps inspired by the recent releases of effects-heavy blockbusters like Spider-Man and the Lord of the Rings, Eastwood mused, “We have a lot more technology, a lot of toys to play with, but they don’t necessarily do anything to make movies better.”
Amazingly, he then hit on a complaint that plagues modern Hollywood: “Unfortunately, today, when a movie is successful, they try to make twenty more like it.”
With this in mind, an unhappy Eastwood revealed that certain people in Hollywood at that time were pushing him to go back to well one more time on his most enduring character. He snarled, “Some people, for example, have wanted me to do Dirty Harry again.” At that point, Eastwood was 15 years removed from the last time he played renegade cop Harry Callahan in 1988’s The Dead Pool – but he had no intention of bringing him back to appease the industry’s nostalgia merchants.
“Harry or Josey Wales were just characters,” explained Eastwood, “And they came with a dramatic situation. They weren’t like me, and the less they were like me, the more fun it was to do them.” The Unforgiven star admitted that he felt he needed to leave characters like Callahan in his rearview mirror because, if he kept returning, it would stunt his growth as an artist. He confessed, “At some point in your life, that kind of thing becomes less challenging. You have to start to grow within yourself, or else you’ll start going backwards.”
Eastwood’s train of thought then led him to another tough guy icon who was supposedly considering returning to the ring. He admitted, “I don’t understand Sylvester Stallone. I hear he’s going to do Rocky again. For me, it would look like you’re doing it for a paycheque.”
This was quite the accusation for a star of Eastwood’s calibre to make, especially considering Stallone’s journey with everyone’s favourite underdog boxer, Rocky Balboa, played out very similarly to Eastwood’s with Callahan. Both franchises began in the ’70s, with The Dead Pool being Eastwood’s fifth Dirty Harry movie. Two years after it was released, Stallone starred in Rocky V and, as of 2003, hadn’t picked up Balboa’s gloves again.
Some may accuse Eastwood of being hypocritical with this comment, but it’s fascinating to poke beneath its surface. Perhaps Eastwood saw a kindred spirit in Stallone – someone who had built a thriving career around one defining character but then struggled to be viewed as anything else. Maybe he wanted the “Italian Stallion” to push himself more, either in acting or directing, instead of returning to Rocky’s safe territory.
In the end, Stallone did play Balboa again. He made a triumphant return with Rocky Balboa in 2006, then played a supporting role in the first two entries in Michael B Jordan’s spinoff Creed series. As of 2024, though, Eastwood has stuck to his word – ‘Dirty’ Harry Callahan has been left in the past, where his star thinks he belongs.
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