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50 free Chicago (2002 Film) trivia questions with answers — entertainment quiz, new questions added Aug 2026.
Chicago was the first musical in 34 years to win Best Picture, and it did it with a first-time director, a star who turned down the lead, and two real murderesses from 1924 behind its heroines. These Chicago movie trivia questions cover the cast, the numbers from All That Jazz to Razzle Dazzle, the Toronto shoot, the Broadway original and revival, and the awards. Every answer is sourced, with a short explanation so you learn something even when you miss.
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Q 01How many Academy Awards did Chicago win in 2003?
Six
Best Picture headed the list, along with Best Supporting Actress for Catherine Zeta-Jones.
Q 02Chicago was the first musical to win Best Picture since which 1968 film?
Oliver!
The 34-year gap ended a drought that even Cabaret, Bob Fosse's 1972 Oscar winner, could not break.
Q 03Who plays Roxie?
Renée Zellweger
Theron, Applegate, Marisa Tomei, Mira Sorvino and Jennifer Aniston were among those considered for the part.
Q 04Who plays Velma?
Catherine Zeta-Jones
She opens the film with 'All That Jazz' moments before her arrest.
Q 05Who plays Billy, the smooth-talking lawyer?
Richard Gere
He won the Golden Globe for Best Actor in a Musical or Comedy for the role.
Q 06Which star was offered the lawyer role and turned it down?
John Travolta
Travolta had famously passed on Chicago once before, when Bob Fosse's version was in development.
Q 07Which pop star was considered for the lawyer role before Harvey Weinstein objected?
Michael Jackson
Weinstein worried the singer would draw more attention than the rest of the cast.
Q 08Who plays Matron 'Mama' Morton?
Queen Latifah
Her number 'When You're Good to Mama' lays out the jail's system of bribes.
Q 09Who plays Roxie's devoted husband Amos?
John C. Reilly
He earned an Oscar nomination for Best Supporting Actor.
Q 10Which song is Amos's solo about being ignored by everyone?
"Mister Cellophane"
It follows the press shrugging him off after Roxie's pregnancy announcement.
Q 11Who plays heiress Kitty Baxter?
Lucy Liu
Her arrest instantly pulls the press and the lawyer away from Roxie.
Q 12Kitty Baxter steals the headlines after killing her husband and whom?
His two mistresses
Roxie wins the spotlight back by announcing she is pregnant.
Q 13What role does Taye Diggs play?
The bandleader
His shadowy master of ceremonies introduces each musical number.
Q 14Christine Baranski plays which sensationalist reporter?
Q 21The film's credits include a dedication to Fosse, his wife Gwen Verdon and which Broadway producer?
Robert Fryer
Fryer, Verdon and Fosse had bought the rights from the playwright's estate after her death in 1969.
Q 22In which city was the film actually shot?
Toronto
Principal photography ran from December 2001 to April 2002 at sites including Casa Loma and the Elgin Theatre.
Q 23The courtroom scenes were filmed in which landmark building?
Osgoode Hall
The building is the home of the Law Society of Ontario, making it a fitting stand-in for a Cook County courtroom.
Mary Sunshine
In the film she is a radio personality as well as a newspaperwoman.
Q 15Dominic West plays which character, Roxie's lover and victim?
Fred Casely
He admits he lied about knowing the nightclub manager just to sleep with her, and she shoots him.
Q 16What is the occupation of Roxie's lover?
Furniture salesman
He had promised to introduce her to the manager of the Onyx club.
Q 17Who directed Chicago, in his feature directorial debut?
Rob Marshall
He also choreographed the film and later directed Nine, Into the Woods and Mary Poppins Returns.
Q 18Who wrote the screenplay?
Bill Condon
Condon's script presents the musical numbers as fantasies inside Roxie's head.
Q 19Who composed the music, to Fred Ebb's lyrics?
John Kander
Kander and Ebb modelled each number on a traditional vaudeville act or performer.
Q 20Who directed and choreographed the original 1975 Broadway production?
Bob Fosse
He planned to film it himself after Cabaret but died first; his jazz style is all over the 2002 movie.
Q 24Which journalist wrote the 1926 play on which the musical is based?
Maurine Dallas Watkins
She covered the real trials for the Chicago Tribune and later refused for years to sell the musical rights.
Q 25Roxie was modelled on which real accused murderer of 1924?
Beulah Annan
Her husband bankrupted himself paying for her defence, and she dumped him the day after her acquittal.
Q 26Velma was based on which real cabaret singer and society divorcée?
Belva Gaertner
She even made a cameo in the 1927 silent film version of the story.
Q 27What was the title of the 1942 Ginger Rogers film adapted from the same play?
Roxie Hart
Under the Hollywood Production Code, its Roxie had to be innocent of the killing.
Q 28Which studio produced Chicago?
Miramax
The Producers Circle and Germany's Kallis Productions were co-producers.
Q 29At which nightclub does Velma perform 'All That Jazz' in the opening scene?
The Onyx
The spotlight lingers on the empty spot where her sister should be in the double act.
Q 30In which year is the film set?
1924
The real trials that inspired the story were held in Chicago that same year.