In Old Chicago - 1938

Alice Brady won a Best Supporting Actress Oscar for her role in this film. Brady wasn't present at the award ceremony, but a man walked up and accepted the award on her behalf. After the show, he and the Oscar were never seen again. She was the first person to win the Supporting Oscar after being nominated in the prior year.

MGM had originally planned to "loan out" Jean Harlow to Twentieth-Century Fox for the role of Belle Fawcett (ultimately played by Alice Faye), in exchange for acquiring Shirley Temple to play the role of Dorothy in Wizard of Oz, The (1939). The deal fell through when Harlow died in June 1937.

The portrayal of the O'Leary family is completely fictitious down to the names of the characters. Mrs. O'Leary's name was Catherine, not Molly.

The O'Learys had two children, one son and one daughter. (In the movie there are 3 sons) Her only son was named James. The daughter was named Anna.

Patrick O'Leary did not die in 1854 as a result of an accident involving his horses. He died in 1894.

Mrs O'Leary did not run her own "French Laundry" out of their house.

The Mayor of Chicago in 1871 was Roswell B. Mason, not an O'Leary son.

Cast of In Old Chicago

Tyrone Power as Dion O'Leary
Alice Faye as Belle Fawcett
Don Ameche as Jack O'Leary
Alice Brady as Mrs. Molly O'Leary
Phyllis Brooks as Ann Colby
Andy Devine as Pickle Bixby
Brian Donlevy as Gil Warren
Tom Brown as Bob O'Leary
Berton Churchill as Senator Colby
Sidney Blackmer as General Phil Sheridan
J. Anthony Hughes as Patrick O'Leary
Paul Hurst as 'Mitch' Mitchell
June Storey as Gretchen O'Leary