Round 1: Singin' in the Rain vs The Roaring Twenties

The Roaring Twenties is the end of an era for the gangster drama. And what perfect way to draw the curtain on a decade-long ascent than to go on the ride with the great James Cagney, who helped popularize the genre with The Public Enemy. The Roaring Twenties is an epic film in scope, spanning from 1919-1933, from World War I, through prohibition, the economic flourishes of the decade to everything in between. Walsh directs this film in an efficient and economic manner, covering over a decade’s worth of major events in less than two hours. Cagney’s transformative performance helps brings a humanity to his morally conflicted character. Eddie Bartlett is a tragic figure, rejected by the country he served and the woman he loves. The film brilliantly juxtaposes the victory of World War I with Bartlett’s descent as a character, and subsequent rise in the criminal underworld. And the underrated Gladys George delivering one of the great movie endings of all-time..."He used to be a big shot."

What else can be said about Singin' in the Rain? Arguably the definitive musical, it's similar to Casablanca in that, it wasn't necessarily expected to be the biggest hit, but all the pieces coalesced to create a masterwork. The songs are recycled from previous films, yet Gene Kelly, Arthur Freed, Betty Comden and Adolph Green found a way to integrate the songs with the plot that it seemingly feels as though they were created specifically for the film. One memorable scene after another, and as director Brad Bird describes the singin' in the rain number as perhaps, "the greatest representation of pure joy that has ever been on screen."