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Best Picture Series — Chicago (2002) Review

12/19/2025

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Evan D.

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​As a project this year we are taking a trip through time to revisit all of the Best Picture winners in history, Wings to Anora. Chicago is the seventy-fifth film in that series, to see all the other Best Picture reviews, click here.

For many years it was the movie musical that reigned supreme over Hollywood. Readers of this series will recall how films like An American in Paris and My Fair Lady tap danced their way to Best Picture. Then, Hollywood mostly abandoned the genre for decades. With Chicago, Rob Marshall showed that a big show stopping musical can still stop the show when done right. 

Roxie Hart (Renee Zellweger) is an aspiring vaudevillian willing to do whatever it takes to see her name in the marquee lights. Specifically she is willing to embark on an affair with a man she met at the bar claiming to be able to get her on the stage. When it turns out he lied to get her to bed, Roxie shoots him down and suddenly the only stage she’ll be seeing is in a courtroom. In prison, Roxie lands on murderess row with all the other women in Chicago awaiting trial for killing someone. Run by the corrupt Mama Morton (Queen Latifah,) the women of murderess row know their chances of survival rest on the sympathy they can gin up in the press. 

Among the other prisoners is Velma Kelly (an incomparable Catherine Zeta-Jones,) an idol to Roxie for her success on the stage. Those two, as well as the other prisoners, fight for the attention and legal counsel of Billy Flynn (Richard Gere,) a sleazy but successful defense lawyer. Throughout their incarceration and trials, Roxie, Velma and all the other prisoners imagine elaborate vaudeville inspired musical numbers that heighten what they are going through. 

When done well, very few films are able to reach the awe inducing heights that a musical can. Chicago is one of those films. Marshall’s film does it with a pretty wide variety of catch and well choreographed numbers. The opening song, ‘All That Jazz,’ is classic vaudeville and shines almost exclusively on the back of an incandescent performance of the number by Zeta-Jones. ‘We Both Reached for the Gun’ is more campy with Gere and Zellweger performing it as a puppet master and marionette, respectively. Even John C. Riley (playing Roxie’s husband Amos) gets a fun broadway type number that highlights the unique way he’s always been able to use his comedic leanings to accentuate his dramatic touch. 

Given the diminishing returns of Marshall’s later work it is almost surprising to see just how sharp Chicago is in contrast. The broadway musical it is based on has been cut down here in a way that really helps the story move along and the cadence of drama and song is exceptionally paced. His work choreographing the film cannot be discounted either as it elevates the music in a way many modern musicals don’t. Choreography was at the heart of the old Gene Kelly pictures and lackluster dance numbers in newer musicals sap something from them. Chicago does not suffer the same problem.

While Zeta-Jones lights up the screen in her Oscar winning supporting role, she does feel underutilized. Zellweger is good but doesn’t bring quite the same go-for-broke energy as her co-star, ultimately ending up a bit overshadowed. Gere feels almost entirely miscast here. He’s not the same caliber of song and dance performer as the women in the movie, more fit for the dramatic scenes than the musical ones. 

All the same, it’s a delight to see a movie made this century that revels in musical tropes and is targeted at adults. For as dark as the actual story is, Chicago is an absolute blast for the ways it leans into that darkness. How unfortunate that Marshall has settled into a role making these forgettable Disney musicals, the edge he shows here is missed. Long live the big, bold Hollywood musical. 8/10
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