The “terrible” Kirk Douglas movie Clint Eastwood hated watching: “Oh god, what have they done?”

While Clint Eastwood was inevitably compared to John Wayne when he became a star in the 1960s, mostly because he’d been made famous by the western, he had a lot more in common with Kirk Douglas.

In fact, the erstwhile ‘Man with No Name’ pointed to the Spartacus star as an influence, calling him a “terrific” actor who had a “mysterioso quality” and a style that was more “aggressive” than his peers, and many of those labels also apply to Eastwood’s signature no-frills combination of charisma and presence.

Douglas was also a fairly prolific producer who enjoyed building projects from the ground up, and he even directed a couple of pictures himself. Of course, Eastwood evolved into arguably the greatest double threat of actor and filmmaker the industry has ever seen, so they were definitely kindred spirits in a way.

They never starred in a film together, but they knew each other, as you’d expect from two renowned stars who reigned as a pair of the industry’s most in-demand leading men at the same time. There was a deep mutual respect between them, although there was one entry in Douglas’ filmography that left Eastwood distraught.

Why? Jazz, obviously. The four-time Academy Award winner has been a lifelong fan of the genre, and he even brought his passion to the screen when he helmed Bird, the 1988 biopic that saw Forest Whitaker playing Charlie Parker. It was a love letter to an art form and a musician that he adored, so when he saw a shitty jazz film, he wasn’t best pleased.

On paper, 1950’s Young Man with a Horn should have been great. Loosely inspired by the life and times of the influential Bix Beiderbecke, it had all the makings of a prestige drama. Douglas was cast as Rick Martin, with two-time Oscar-winning Casablanca director Michael Curtiz calling the shots, and the two female leads were played by Lauren Bacall and Doris Day.

It was a star-powered production, albeit one that failed to live up to the sum of its parts. As a jazz aficionado, Eastwood was excited to see it on the big screen, years before he’d even made his screen debut in 1955’s Revenge of the Creature. By the time the credits rolled, he was crestfallen.

“The breathing was off, the dubbing was terrible,” he remarked. “And the plot line? I thought, ‘Oh god, what have they done?’ and went out of the theatre dejected.” There are few things worse than being left disappointed by a movie you’ve been looking forward to, and Young Man with a Horn was one of those moments for the young Eastwood.

At the time, his dream of making a jazz movie that didn’t suck seemed a million miles away, but he got there eventually, almost 40 years after Douglas’ attempt had left him so devastated.

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