In Old Chicago [78734] Released: 1938-04-15 Revenue: $0 Budget: $10,000,000 Profit: $-10,000,000 Runtime: 111 mins Popularity: 0.6208 Vote Average: 6.476 Vote Count: 41 Overview: The O'Leary brothers -- honest Jack and roguish Dion -- become powerful figures, and eventually rivals, in Chicago on the eve of its Great Fire. Cast [41] Tyrone PowerDion O'Leary Alice FayeBelle Fawcett Don AmecheJack O'Leary Alice BradyMolly O'Leary Andy DevinePickle Bixby Brian DonlevyGil Warren Phyllis BrooksAnn Colby Tom BrownBob O'Leary Sidney BlackmerGeneral Phil Sherida Berton ChurchillSenator Colby June StoreyGretchen Paul HurstMitch Tyler BrookeSpecialty Singer J. Anthony HughesPat O'Leary Gene ReynoldsDion O'Leary Bobs WatsonBob O'Leary Billy WatsonJack O'Leary Madame Sul-Te-WanHattie Spencer ChartersCommissioner W.J. Be Rondo HattonRondo - Body Guard Thelma ManningCarrie Donahue Ruth GilletteMiss Lou Eddie CollinsDrunk Scotty MattrawBeef King Joe TwerpStuttering Clerk Clarence WilsonLawyer Frank DaeJudge Harry StubbsFire Commissioner Joe KingShip's Captain Francis FordDriver Bob MurphyPolice Officer Wade BotelerPolice Officer Gustav von SeyffertitzDutch - Politician i Russell HicksPolitician in Jack's Brooks BenedictCourtroom Spectator George ChandlerOnlooker Bess FlowersWoman with Colby Vera LewisWedding Witness Bert MoorhouseOpening Night Guest William H. O'BrienSenate Waiter Martin TurnerRefugee Trailers