Grapes of Wrath Okies in the Dustbowl struggle to live amongst dying crops and farm foreclosures.
Ironweed (Sort of graphic, maybe NSFW) A pair of ne'er do wells (Meryl Streep and Jack Nicholson) rage and romance in Depression-era Albany.
Bonnie & Clyde Clyde Darrow and Bonnie Parker, played by Warren Beatty and Faye Dunaway, take to the bank robbing life during the 1930's. They meet a bullety end.
Annie A bunch of orphans struggle through the Depression, hoping for rescue. Songs include "The Hardknock Life" and "We Would Like to Thank You, Herbert Hoover."
Paper Moon A grifter and his precocious young daughter con their way through 1930's America.
Road to Perdition A stoic hitman for the Chicagoland mob, Tom Hanks, takes to the road after his associates turn on him. Really a stunningly beautiful film, the last shot by the great cinematographer Conrad Hall. A modern classic.
Of Mice and Men From the Steinbeck novel about a pair of migrant farmers roaming 1930's California.
O Brother, Where Art Thou? The Coen brothers' Depression-set adaptation of 'Ulysses,' about prison escapees and the music they make.
They Shoot Horses, Don't They? A grueling dance marathon contest is held during the Depression, in which desperate people compete for hours and days while a cruel emcee manipulates them.
The Purple Rose of Cairo A bored and sort of sad 1930's gal (Mia Farrow) enjoys a romance with a movie character come to life (Jeff Daniels) in this Woody Allen comedy.
Cradle Will Rock A truly beautiful film about art and censorship, "Cradle Will Rock" tells the story of a controversial play and the artists who struggled to keep it running. Please watch.
Modern Times The Charlie Chaplin silent classic about his famous Tramp character navigating a troubled modern world.
Dogville A disturbing but compelling film, Danish director Lars von Trier strips away all the scenery to tell the story of a Depression-era daughter of the mob (Nicole Kidman) who is first welcomed, then exploited by the denizens of a small Colorado town. Not for the faint of heart.
Hallelujah I'm a Bum An Al Jolson musical about hobos.
Hard Times A Charles Bronson rock 'em sock 'em about a street fightin' drifter during the Depression.
The Color Purple The story of a kept woman, Celie, and her struggles to find her inner strength in the Depression-era Deep South.
Angela's Ashes It went to Europe, too! The movie adaptation of Frank McCourt's memoir about his youth in Ireland.
Rambling Rose Laura Dern's daddy, Robert Duvall, sells her into prostitution. Basically.
Gold Diggers of 1933 A silly musical about actresses. Features the Depression classic "We're In The Money."