
Ride with the Devil
1999 · Movie · R · 138 min · ★ 6.3 · 67% critics
During the American Civil War on the Missouri–Kansas border, a small band of guerrilla fighters and civilians are thrown together in a lawless landscape where neighbors become enemies. As violence escalates and loyalties are tested, an unlikely friendship forms, forcing them to confront survival, freedom, and what honor means in a brutal conflict.
Also known as Ride with.the.Devil
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Details
- Years
- 1999
- Release date
- 1999-11-24
- Language
- English
- Rated
- R
- Runtime
- 138 min
- Critic score
- 67/100
- TMDB rating
- 6.3/10 (209 votes)
About
You’ll likely enjoy this if you want a gritty, morally complicated Civil War border story that mixes brutal raids with quieter character moments, similar in feel to The Long Riders; Not for you if you need nonstop action or clear-cut heroes.
Pros: authentic period atmosphere; complex friendships; intense battle moments | Cons: slow middle stretch; hard-to-follow dialect; uneven pacing and focus
Themes
- civil war
- based on novel or book
- missouri
- friends
- bush whacker
- raid
- american civil war
- 1860s
Cast & crew

Skeet Ulrich
as Jack Bull Chiles

Tobey Maguire
as Jake Roedel

Jewel
as Sue Lee Shelley

Jeffrey Wright
as Daniel Holt

Simon Baker
as George Clyde

Jonathan Rhys Meyers
as Pitt Mackeson

Tom Wilkinson
as Orton Brown

Jim Caviezel
as Black John

Tom Guiry
as Riley Crawford

Jonathan Brandis
as Cave Wyatt
Directed by Ang Lee