He would make his film debut with a small role in 1939's I Stole a Million, which stars George Raft and Claire Trevor. He would have his first memorable bit in his next film, Destry Rides Again, starring Marlene Dietrich and James Stewart, where in the opening scene he is playing cards, and is cheated when Dietrich distracts him by spilling coffee in his lap. His film career would span almost forty years, and encompass over 90 films, mostly in small or supporting roles, although with an occasional starring role, as in 1940's Zanzibar. The 1940s would see him appear in other classic and notable films such as: the Bob Hope comedy, My Favorite Blonde (1942); Pardon My Sarong (1942), starring the comedy team of Abbott and Costello; The Naughty Nineties (1945), again starring Abbott and Costello; the film noir, The Big Sleep (1946), starring Humphrey Bogart and Lauren Bacall; and 1946's It's a Wonderful Life, where he had a particularly memorable scene as the Tollhouse Keeper on the bridge, who reacts to Clarence's (the angel) explanation of who he is to George Bailey (James Stewart).