Hugh Jackmanhas been one of Hollywood’s biggest stars for decades, and he, thankfully, is showing no signs of slowing down. He returned to his Marvel roots this summer alongsideRyan ReynoldsinDeadpool & Wolverine, which was amassive box office successthat officially welcomed his iconic character into the MCU. Additionally, he starred inMusic Manon Broadway, which was also a giant success, showing off his impressive range as a performer. It’s no surprise, then, that the MCU star has a number of musical movies under his belt, includingLes MisérablesandThe Greatest Showman. However, it might be a big surprise to learn that Jackman actually passed onthe crime comedy musical,Chicago.

What Is ‘Chicago’ About?

ChicagostarsRichard Gere,Catherine Zeta-Jones, andRenée Zellweger. Released in 2002, the film follows Roxy Hart (Zellweger), a housewife in 1920s Chicago who dreams of becoming famous, and is obsessed with a local star, Velma Kelly (Zeta-Jones). Velma then gets arrested one night after murdering her husband and sister, and Roxy simultaneously gets arrested for murder. Killing the man she was having an affair with, she realized he was lying about the connections he had that could make her a star. Roxy and Velma find themselves in Cook County Jail awaiting trial at a time when the death penalty was still in play, and both hire the corrupt lawyer, Billy Flynn (Gere).Flynn can seduce any jury with his finesse, and vows to get both women off without charges— all while making them stars in the process.

Chicagohas long been considered one of the greatest musicals of all time.It was originally a groundbreaking play in 1926 during the age of the flapper, which saw a rise in feminism across America, andembraced stories of murderous women. It was then adapted into the 1975 stage musical of the same name, by Broadway director and choreographer extraordinaire,Bob Fosse.Fosse’s stylized jazz numbers featuring raging women performing impressive stunts mesmerized audiences, and the musical won numerous Tony Awards, in addition to leaving an important legacy behind of female-led productions.

Catherine Zeta-Jones as Velma Kelly with a bob cut and black dress in ‘Chicago’

Why Did Hugh Jackman Pass on ‘Chicago’?

Hugh Jackman revealed in an interview with the Australian radio broadcast show, KIIS, thathis biggest regret in rejecting a rolecame when he rejected the offer of playing Billy Flynn inChicago, which hasbecome a defining role for Gere. A performance that requires not only a great actor, but a singer and dancer too,it makes sense why Jackman was the perfect fit for the sleazy, high-energy lawyer.Jackman lamented about his regretfor passing up the chance to play him when he was offered the part, and that it had to do with his age at the time:

“I was offered the Richard Gere role…and I thought I was too young for it, ‘cuz he has a line where he says, ‘I’ve seen it all kid.’ One of the last lines. And I was like, man, I’m 31, I can’t do that. Richard Gere won the Golden Globe, it won the best picture at the Oscars. Maybe I should have put a little bit of make-up on. Idiot.”

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Richard Gere himself, similar to Jackman, has a career rooted in musical theater that began on stage. He evenplayed the role of Danny Zukoin a West End production ofGreasein the ’70s. InChicago,it was Gere’s opportunity to show off the extent of his talents as a song and dance man.Performing classic numbers like the show-stopping, “We Both Reached For the Gun,” he masterfully tap-dances at a jaw-dropping pace. Had Jackman played Billy Flynn, he could have shown off his dance training, which he showcased while doing high kicks and tap dancing as he portrayed Peter Allen in the Broadway musical,The Boy From Oz. It won him a Tony Award in 2004, proving he would have been more than capable of the demanding requirements for the part.

Chicagowon five Academy Awards, including for Best Picture, Best Supporting Actress for Zeta-Jones, Best Art Direction, Best Costume Design, and Best Film Editing. Directed byRob Marshall, the film has stood the test of time, and is included onAFI’s 25 Greatest Movie Musicals of All Time.While Jackman carries regret for not taking on the role of Billy Flynn to this day, his career is thriving.Deadpool & Wolverinehas now set the record for being thehighest grossing R-rated movie of all time.

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Chicagois available to watch on Hulu in the U.S.

Watch on Hulu

Two death-row murderesses develop a fierce rivalry while competing for publicity, celebrity, and a sleazy lawyer’s attention.

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Hugh Jackman