This was the first of three films that teamed Tyrone Power and Alice Faye, the others being Alexander's Ragtime Band and Rose of Washington Square. In Old Chicago and Alexander's Ragtime Band also had Don Ameche in it. And it set a pattern, no way was Ameche going to get Faye when Power was on the scene.
Ty Power's roles in his Fox days fell in two Categories. He was either the total romantic hero or he was a hero/heel. In In Old Chicago he's the latter although Power usually has the heroic side win out in these parts, he's not above a little scheming. Power's Dion O"Leary both double crosses Brian Donlevy and marries Alice Faye not just because he loves her, but so she can't testify against him. But Ty's always a charming likable cuss and Ameche is always the straight arrow, but slightly dull rival and in this case, brother.
However the film is known for two things. It gave Alice Faye her first real notice as actress. Up to this point, she'd been a Jean Harlow wannabe right down to the platinum blonde hair. Here Faye gets those period costumes that she wore so well. It was the first of many successes in that genre.
The second thing is the grand special effects showing the burning of Chicago. Even almost 70 years later it's a spectacular sight.
