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Community reviews
From TMDb members · 1 total- CinemaSerf6/10
The two "O'Leary" brothers grow up without their father in an house where their widowed mother runs quite a successful laundry business. One son, "Jack" (Don Ameche), shows promise as a lawyer; the other "Dion" (Tyrone Power) is a more inventive sort of fella. After a few, quite…
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In Old Chicago
“The Great American Motion Picture!”
67%
Movie
1h 51m
AI Analysis
In Old Chicago (1938) — AI movie analysis
WatchMind AI generated this AI analysis of In Old Chicago (1938) — a movie tagged as Drama and History with epic moods and steady pacing.
Story & themes: The O'Leary brothers -- honest Jack and roguish Dion -- become powerful figures, and eventually rivals, in Chicago on the eve of its Great Fire. Our models also surface themes such as identity, conflict, and relationships from synopsis and genre signals.
Watch context: Best suited for general audiences. Expect steady storytelling (~111 min).
Community signal: TMDb members rate In Old Chicago 67% (48 votes) — solid community ratings for this movie.
AI verdict
Use this AI analysis as a quick read on In Old Chicago before you watch — trailer, TMDb reviews, and licensed streaming links on this page help you decide.
Algorithmic AI analysis from genres, synopsis, pacing heuristics, and TMDb community scores — not a generative chatbot. How WatchMind works.
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TMDb audience score
67%
from 48 TMDb votes
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Synopsis
The O'Leary brothers -- honest Jack and roguish Dion -- become powerful figures, and eventually rivals, in Chicago on the eve of its Great Fire.
Quick facts
- Type
- Movie
- Status
- Released
- Release date
- 1938-04-15
- Runtime
- 1h 51m
- TMDB rating
- 6.7
- TMDB ID
- 78734
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Where can I watch In Old Chicago (1938)?
In Old Chicago is available for discovery on WatchMind. You can find official links to rent, buy, or stream from licensed digital stores like Apple TV and Amazon in our "Where to Watch" section.
Is there an official trailer for In Old Chicago?
Yes, you can watch the official trailer for In Old Chicago directly on this page. We pull the latest video metadata from TMDb and play it via YouTube integration.
What is In Old Chicago about?
The O'Leary brothers -- honest Jack and roguish Dion -- become powerful figures, and eventually rivals, in Chicago on the eve of its Great Fire.
Is there an AI analysis for In Old Chicago?
Yes. WatchMind publishes an AI analysis on this page — tone, pacing, audience fit, and community scores from TMDb metadata and recommendation models (not a chatbot). Scroll to the AI Analysis section or read the meta description summary.
How long is the movie In Old Chicago?
The official runtime for In Old Chicago is approximately 111 minutes.
Cast & crew
Names and photos from The Movie Database (TMDb). Follow links on themoviedb.org for full filmographies.
Cast

Tyrone Power
Dion O'Leary

Alice Faye
Belle Fawcett

Don Ameche
Jack O'Leary

Alice Brady
Molly O'Leary

Andy Devine
Pickle Bixby

Brian Donlevy
Gil Warren

Phyllis Brooks
Ann Colby

Tom Brown
Bob O'Leary

Sidney Blackmer
General Phil Sheridan

Berton Churchill
Senator Colby

June Storey
Gretchen

Paul Hurst
Mitch

Tyler Brooke
Specialty Singer

J. Anthony Hughes
Pat O'Leary

Gene Reynolds
Dion O'Leary (as a boy)

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

Madame Sul-Te-Wan
Hattie
Audience notes
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Community reviews
Written by TMDb members — same catalogue as our movie & TV metadata. API terms
The two "O'Leary" brothers grow up without their father in an house where their widowed mother runs quite a successful laundry business. One son, "Jack" (Don Ameche), shows promise as a lawyer; the other "Dion" (Tyrone Power) is a more inventive sort of fella. After a few, quite entertaining wooing antics, the latter hooks up with visiting chanteuse "Belle" (Alice Faye) and together they start a business that rapidly expands so as to soon dominate the rather rundown "Patch" area of Chicago. The city government is riddled with corruption and so a group of civil libertarians nominate brother "Jack" to be mayor - a plan supported, for other reasons, by his now very wealthy sibling. It's only a matter of time before the two clash - but who will prevail? Power is charming and engaging here, he has a twinkle in his eye and there is certainly some chemistry between him and Faye. The ending, though impressive to watch with all the pyrotechnics of the Great Fire of 1871 that devoured thousands of the predominantly wooden structures of the area, is all a bit hurried and weak. The more interesting political and personal struggles between the two men, and agitator "Warren" (Brian Donlevy) should have featured more, with less emphasis on the initial character development and I could have done without the musical numbers that though ably enough performed by Faye, just sucked too much of the pace of this Cain and Abel style of story. Still, it's enjoyable to watch and gives us a hint at just how corruption and power-brokering functioned back then.
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