In four films made from 1926 to 1932, Don Juan, Eternal Love, Arsene Lupin, and Grand Hotel, John Barrymore played a series of leading men embroiled in passionate affairs. He showed himself adept at playing the accomplished flirt, the psychologically damaged lothario, the drunken target of seduction, and the sophisticated partner in crime. As this essay shows, these roles display a breadth of characterization and reveal Barrymore’s skill as an actor in both silent and sound films.