In Old Chicago
1938-04-15The O'Leary brothers -- honest Jack and roguish Dion -- become powerful figures, and eventually rivals, in Chicago on the eve of its Great Fire.

The O'Leary brothers -- honest Jack and roguish Dion -- become powerful figures, and eventually rivals, in Chicago on the eve of its Great Fire.

Dion O'Leary
Tyrone Power

Belle Fawcett
Alice Faye

Jack O'Leary
Don Ameche

Molly O'Leary
Alice Brady

Pickle Bixby
Andy Devine

Gil Warren
Brian Donlevy

Ann Colby
Phyllis Brooks

Bob O'Leary
Tom Brown

General Phil Sheridan
Sidney Blackmer

Senator Colby
Berton Churchill

Gretchen
June Storey

Mitch
Paul Hurst

Specialty Singer
Tyler Brooke

Pat O'Leary
J. Anthony Hughes

Dion O'Leary (as a boy)
Gene Reynolds

Bob O'Leary (as a boy)
Bobs Watson
Jack O'Leary (as a boy)
Billy Watson

Hattie
Madame Sul-Te-Wan

Commissioner W.J. Beavers
Spencer Charters

Rondo - Body Guard
Rondo Hatton
Carrie Donahue
Thelma Manning

Miss Lou
Ruth Gillette

Drunk
Eddie Collins
Beef King
Scotty Mattraw
Stuttering Clerk
Joe Twerp

Lawyer
Clarence Wilson

Judge
Frank Dae

Fire Commissioner
Harry Stubbs

Ship's Captain
Joe King

Driver
Francis Ford
Police Officer
Bob Murphy

Police Officer
Wade Boteler

Dutch - Politician in Jack's Office
Gustav von Seyffertitz

Politician in Jack's Office
Russell Hicks

Courtroom Spectator (uncredited)
Brooks Benedict

Onlooker (uncredited)
George Chandler

Woman with Colby (uncredited)
Bess Flowers

Wedding Witness (uncredited)
Vera Lewis
Opening Night Guest (uncredited)
Bert Moorhouse

Senate Waiter (uncredited)
William H. O'Brien
Refugee
Martin Turner