Michael Douglas names the biggest disappointment of his career: “That was a punch in the gut”

Much like his father, Michael Douglas was every bit as successful as a producer if he was an actor, even if his first taste of serious gold strained his relationship with his legendary old man.

Kirk Douglas had originally optioned the rights to turn One Flew Over the Cuckoo’s Nest into a movie, having previously played the part of Randall P McMurphy on Broadway in the original production, but by the time the feature-length adaptation finally rolled around, he’d aged out of the part.

His son remained on board as a producer, however, which caused plenty of friction when Jack Nicholson won an Academy Award for ‘Best Actor’ in a film that also won ‘Best Picture’. It was an important moment for Douglas, though, because having that kind of ruthless streak is necessary for anyone who wants to make it to the top.

He’s won a ‘Best Actor’ trophy of his own for headlining Oliver Stone’s Wall Street and taken home five Golden Globes for his on-camera efforts, but Douglas also developed a habit of being able to sniff out a decent project or two in a producorial capacity.

Some of his behind-the-camera credits where he didn’t appear as a member of the cast include Joel Schumacher’s hit psychological horror Flatliners, John Woo’s action-packed blockbuster Face/Off, Francis Ford Coppola’s John Grisham adaptation The Rainmaker, and John Carpenter’s cosmic romantic drama Starman.

That, coupled with his status as one of the most recognisable leading men in Hollywood, led many to believe – Douglas included – that he had a pretty good understanding of how the industry worked. At least, that’s what he thought until he was knocked for a loop when Wonder Boys bombed.

Curtis Hanson’s 2000 dramedy may have won an Oscar for ‘Best Original Song’ thanks to Bob Dylan penning ‘Things Have Changed’ for the soundtrack, and it received two further nods for ‘Best Film Editing’ and ‘Best Adapted Screenplay’, but that was about as good as things got.

Wonder Boys was a huge disappointment, personally,” Douglas told Film Scouts. “I loved the movie; it had a fantastic screenplay and a great cast. It was a movie that was a punch in the gut. It hurt my confidence in terms of understanding what was going on. We didn’t even get critically acknowledged, as far as awards go.”

Douglas starred alongside Tobey Maguire, Frances McDormand, Katie Holmes, and Robert Downey Jr as a professor suffering from writers’ block who tries to balance the complexities of his personal life with the problems of his students. Like he said, it had a great cast and a great script, and it got strong reviews, but it still flopped twice over.

After it underperformed during its initial release, the studio went back to the drawing board and came up with a revised marketing strategy, only for the re-release to yield similar results. Douglas thinks it’s a great movie, and he was left questioning his instincts when it failed.

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