Up the River (1938)

Card sharps Chipper Morgan and Darby Randall pick the wrong victim, Detective Willis, on a transatlantic crossing, and are arrested upon docking in New York and returned up the river to Rockwell Prison, their old alma mater. They had played brilliant football for "dear old Pen" during their prior semesters, and prison coach Slim Nelson is happy to see them back for graduate work, especially with the annual grudge game with Larson State Pen coming up. Willis, who has been named the new warden for Rockwell, gives them soft jobs and then places a large bet on the Larson eleven. Both Chipper and Darby feel badly about the raw deal handed fellow "student" Tommy Grant and his sweetheart, Helen, who were innocently caught up in a phony pension racket ran by swindlers Jeffrey Mitchell and Ray Douglas, and were both jailed. When Phyllis is released from Stillwell Prison for Women, she tells Tommy about the two men and their racket, and he decides to escape, even though he has only a month more to serve, and put an end to their scheme. He plans his break for the night of the prison's "varsity show" and tells Chipper and Darby, who promise to help him. But the pair tie up Tommy and make the break themselves, dressed as women. They go to Springfield, save the victim's money, get a confession from Mitchell and Douglas clearing Tommy and Helen, turn them over to the sheriff... and race back to Rockwell to find their team behind 14-9 late in the game. Can they lead old Rockwell to a comeback victory?