The Rat Pack—Frank Sinatra, Dean Martin, and Sammy Davis Jr.—in a raucous, uneven musical about a Chicago gangster (Sinatra) who becomes the hero of the city when he (inadvertently) shares his boodle with the poor (1964). Bing Crosby, strangely smarmy, lurks around as a confidence man disguised as a priest; Davis does a terrifying tap-dance number with a machine gun. And yes, you get to hear Frank sing “My Kind of Town.” Gordon Douglas directed; with Peter Falk, Barbara Rush, Victor Buono, and a guest appearance by Edward G. Robinson.