White Heat (1949, Raoul Walsh)

Cagney and his dimwitted men rob a train and kill a lotta guys then hide out, but boring cop John Archer (Destination Moon) and his men are closing in, so Cagney confesses to a different, non-fatal job as an alibi for the train heist and goes to jail for a little while. “A very good friend of mine… me!” sounds like an Odenkirk line.

The cops want more on Cagney so they send Large-faced Eddie “Rock Around the Rockpile” O’Brien to jail as a mole to gain his trust. Rivalries in jail then prison break, while outside Big Ed steals his girl Virgino Mayo (Walsh’s Colorado Territory the same year) and they kill Cagney’s beloved Ma (Margaret Wycherly, fake mystic of The Thirteenth Chair). This is the movie where Cagney is a mother-obsessed seizure-prone psychopath, but I don’t find him any more psychotic than most movie gangsters. The cops track him to the next job with newfangled radio equipment – trapped in a burning building he’s made it, ma, top of the world.