- Saved from Development Hell: Stone of Sisyphus was originally Chicago XXII in 1994. It was eventually released in 2008 as Chicago XXXII, after a label change (the original label was one of the main reasons why it wasn't released in '94) and with one track missing.
- Throw It In: On a lot of the early albums. Many fans got upset when the false start for "Happy Man" got removed from the Rhino remaster of Chicago VII. Also, listen near the end of "Aire" for a more... humorous example.
The original nonmusical play:
- Creator Backlash: The author of the original play, Maurine Dallas Watkins, was a devout Christian from a small town. She was so perturbed by the trials that led to the creation the play that she quit her job as a reporter covering murder trials to become a playwright, beginning with Chicago.
- She would later refuse to sell the play to Bob Fosse, whose wife had asked him to turn it into a musical. Some speculate that this is due to her reluctance to revisit it, likely because she feels guilty for getting the women acquitted due to her reporting. Fosse and his partners did not get the rights until she died, when her estate sold them to Fosse.
- Reality Subtext: The play is Very Loosely Based on a True Story, adapted from cases the author had reported on. The woman Velma was based on attended the original premiere of the play.
- The woman Roxie was based on did not attend the original play, instead dying two years after the release of the play from pneumonia. However, she did indeed fake a pregnancy during the trial and divorced her husband shortly after the trial ended.
- Mary Sunshine is based on the "sob sisters" originated by the Hearst Newspaper company to write sympathetic stories for the accused women. This angle on the murder trials helped sell papers, leading other papers to take up the strategy.
- There was indeed a woman convicted partially due to her inability to speak English. In reality, she was Italian, not Hungarian. She was later shown to be innocent.
The Broadway musical:
- Colbert Bump: Of sorts. The 1996 revival was helped by the real-life O.J. Simpson trial, which highlighted celebrity, murder, and getting away with it. One program even described the show as "Outrageous in the 20s, scandalous in the 70s, and now just reads like a documentary."
- Stunt Casting: The revival has become known for casting well known actors and singers in the three lead roles.
The musical film:
- AFI's 100 Years… 100 Songs:
- #98, "All That Jazz"
- AFI's Greatest Movie Musicals: #12
- Award Category Fraud: Catherine Zeta-Jones was nominated at the Oscar and BAFTA awards for Best Supporting Actress, even though the role of Velma Kelly in Chicago previously earned Babe Neuworth a Leading Tony.
- Awesome, Dear Boy: Catherine Zeta-Jones was originally approached to play Roxie. Zeta-Jones asked "Who gets to sing 'All That Jazz'?" and when they said "Velma Kelly," she immediately requested to be cast as Velma, even though it was a smaller part, just so she could sing that song.
- Creator Cameo: Chita Rivera has a couple lines in the scene before Mama Morton arrives.
- Cut Song: A few from the stage show, the most notable being Velma's "I Know a Girl", Roxie and Velma's "My Own Best Friend", and Velma and Mama Morton's "Class". The latter was actually recorded for the film and included on the soundtrack album, but cut from the original print for time.
- Dyeing for Your Art: An interesting example. Even though the script didn't call for it, Catherine Zeta Jones decided to cut her hair short for the role because she was afraid that her ordinarily long hair might obscure her face during the dancing scenes, making the audience think that she had a double doing her dancing for her. With the bob haircut that she wears in the movie, there's no doubt that it's really her.
- Fake Nationality: Katalin Helinski (the Hunyak) is a Hungarian character with a Polish surname played by a Russian actress. She also speaks a line of Russian briefly in the film after saying the rest in Hungarian.
- The Other Marty: Charlize Theron was cast as Roxie when Nicholas Hytner was set to direct. After he dropped out, she had to audition again for Rob Marshall - and lost the part to Renee Zellweger.
- Reality Subtext: Renee Zellweger had no singing or dancing training before the movie, mirroring how Roxie is an inexperienced character who has to learn along the way.
- What Could Have Been:
- Catherine Zeta-Jones was originally approached to play Roxie, but wanted to play Velma because of the song "All That Jazz".
- Britney Spears was supposed to play the heiress in this movie. Mandy Moore likewise auditioned but was turned down for being too young.
- Hugh Jackman was offered the role of Billy Flynn, but he turned it down, as he felt that he was too young for the part. Later, he admitted that he regretted making that decision. John Travolta was repeatedly offered the part but kept turning it down. He too later said he regretted it.
- Film rights were bought back in the 1970s, with Bob Fosse to direct. Goldie Hawn, Liza Minelli and Frank Sinatra were announced as stars. Fosse's sudden death caused the project to be shelved.