There aren’t many things Clint Eastwood can’t do, but seeing as his own representatives tried their hardest to convince him it was a potential career-killer, not even those closest to him with his best interests at heart were convinced he had what it took to do comedy.
Having spent the bulk of his filmography on screens both big and small up to that point, playing stoic heroes and gun-toting archetypes, Eastwood was well within his rights to try and freshen things up. His agent and publicist may have been predicting disaster, but the star’s first major comedy turned out to be his biggest hit yet.
When adjusted for inflation, partnering up with an orangutan in Every Which Way but Loose remains the biggest earner out of any of his on-camera efforts, but beyond the sequel Any Which Way You Can, he didn’t make tickling funny bones a recurring habit. Eastwood did dabble in light-hearted, frothy, and frivolous comedy on the odd occasion, but he ended up turning down something so outlandish it would have truly been a sight to see.
Regardless of how many pithy one-liners he could deliver or how many times he flirted with the broadest strokes of comedic performance, Eastwood never went out of his way to give that one showstopping, grandstanding, and wildly exaggerated turn that would have showcased a side of himself audiences never got to find out if he even had or not.
It’s a fascinating thing to think about, but he was the first name on John Landis’ list of potential leading men when he was developing Dick Tracy. The fantastical crime comedy based on the comic strip of the same name eventually became a vehicle for Warren Beatty to both star in and direct, which was also the American Werewolf in London director’s doing after he found himself pushed aside following Eastwood’s rejection.
“Well, Clint Eastwood turned me down,” he lamented to Filmmaker Magazine. “I’m the guy who hired Warren Beatty.” While he was happy to entertain Landis’ pitch, he wasn’t quite as won over by the concept. In fact, he didn’t seem to understand it at all.
“I was preparing Dick Tracy, and I did go to Eastwood, and he said, ‘I’m Dirty Harry, I can’t be Dick Tracy,’ because he was still making Dirty Harry movies at the time,” Landis continued. “I also don’t think he got it, why you would make a comic book movie. But I really had a hard time figuring out who could be Dick Tracy.”
Once Beatty got involved, he ended up acquiring the rights to the property, which then turned the project into a long-running stalemate between the actor and Disney. This meant by the time Dick Tracy was finally released in June 1990, one of the major criticisms of the film was that the star and director was far too old to be playing the title character.
Eastwood’s interest had been gauged well over a decade beforehand, but he decided it wasn’t for him. In the end, Dick Tracy earned in excess of $160million at the box office and won three Oscars for ‘Best Art Direction’, ‘Best Makeup’, and ‘Best Original Song’, roping in a stacked ensemble that numbered Al Pacino, Madonna, Dick Van Dyke, Dustin Hoffman, Kathy Bates, and James Caan.
In another world where Eastwood’s reluctance hadn’t gotten the better of him, it could have been the face of the revisionist western and cinema’s favourite badass cop hamming it up as the hard-boiled detective, which is more than enough to rue it as one that got away based on how unrelentingly bizarre Dick Tracy turned out to be.