
In Old Chicago (1938) | Streaming Guide & Showtimes
In Old Chicago (1938) — The O'Leary brothers -- honest Jack and roguish Dion -- become powerful figures, and eventually Streaming on Amaz...
In Old Chicago (1938) Storyline
The O'Leary brothers -- honest Jack and roguish Dion -- become powerful figures, and eventually rivals, in Chicago on the eve of its Great Fire.
Full Cast & Crew
- Tyrone Power as Dion O'Leary
- Alice Faye as Belle Fawcett
- Don Ameche as Jack O'Leary
- Alice Brady as Molly O'Leary
- Andy Devine as Pickle Bixby
- Brian Donlevy as Gil Warren
- Phyllis Brooks as Ann Colby
- Tom Brown as Bob O'Leary
- Sidney Blackmer as General Phil Sheridan
- Berton Churchill as Senator Colby
- June Storey as Gretchen
- Paul Hurst as Mitch
- Tyler Brooke as Specialty Singer
- J. Anthony Hughes as Pat O'Leary
- Gene Reynolds as Dion O'Leary (as a boy)
Why Watch In Old Chicago?
The Vibe: In Old Chicago is a emotionally complex and thought-provoking drama movie that firmly establishes itself as a must-watch from 1938. The pacing and atmosphere are perfectly calibrated to keep you engaged from start to finish.
Fan Reception: While holding a polarized score of 6.6/10, it retains a dedicated audience who appreciate its specific stylistic choices and unique premise.
Who Should Watch It: Highly recommended for viewers who appreciate deep character studies and powerful performances. If you enjoy character-driven arcs layered with drama-specific tropes, this deserves a spot on your watchlist.
Movie Details & Production
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