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In 1927 Hollywood, a silent film production company and cast make a difficult transition to sound.

'Sugar' Ray is the owner of an illegal casino and must contend with the pressure of vicious gangsters and corrupt police who want to see him go out of business. In the world of organised crime and police corruption in the 1920s, any dastardly trick is fair.

The film explores the world of firefighters in 1920s New York City and tells the story of a 16-year-old girl who will have to become a hero in order to save her city.

New York, 1929, a war rages between two rival gangsters, Fat Sam and Dandy Dan. Dan is in possession of a new and deadly weapon, the dreaded "splurge gun". As the custard pies fly, Bugsy Malone, an all-round nice guy, falls for Blousey Brown, a singer at Fat Sam's speakeasy. His designs on her are disrupted by the seductive songstress Tallulah who wants Bugsy for herself.

Mame Dennis, a progressive and independent woman of the 1920s, is left to care for her nephew Patrick after his wealthy father dies. Conflict ensues when the executor of the father's estate objects to the aunt's lifestyle and tries to force her to send Patrick to prep school.

Set in Prohibition era Chicago, bootlegger Robbo and his cronies refuse to pay the greedy Guy Gisborne a cut of their profits after Guy shoots mob boss Big Jim and takes over. When Big Jim's daughter, Marian, gives Robbo a large sum, believing he has avenged her father's death, the gangster donates to an orphanage, cementing his reputation as a softhearted hood.

Fictional documentary about the life of human chameleon Leonard Zelig, a man who becomes a celebrity in the 1920s due to his ability to look and act like whoever is around him. Clever editing places Zelig in real newsreel footage of Woodrow Wilson, Babe Ruth, and others.

After young playwright, David Shayne obtains funding for his play from gangster Nick Valenti, Nick's girlfriend Olive miraculously lands the role of a psychiatrist—but not only is she a bimbo who could never pass for a psychiatrist—she's a dreadful actress. David puts up with the leading man who is a compulsive eater, the grand dame who wants her part jazzed up, and Olive's interfering hitman/bodyguard—but, eventually he must decide whether art or life is more important.

Molly and Terry Donahue, plus their three children, are The Five Donahues. Youngest son Tim meets hat-check girl Vicky and the family act begins to fall apart.

Murderesses Velma Kelly and Roxie Hart find themselves on death row together and fight for the fame that will keep them from the gallows in 1920s Chicago.

A tale of outsized ambition and outrageous excess, tracing the rise and fall of multiple characters in an era of unbridled decadence and depravity during Hollywood's transition from silent films to sound films in the late 1920s.