Based on a play by Bus-Fekete and directed by Ernst Lubitsch, an indulgent ladies' man tells the devil the story of his life and is sent upstairs.
After dying, Henry Van Cleve (Don Ameche) goes to hell and is questioned by His Excellency (Laird Cregar). Henry tells the story of his life. His mother (Spring Byington) hires a maid to teach him French, and in 1887 she says it is okay to kiss. Grandpapa (Charles Coburn) dismisses her for taking Henry out drinking on his 15th birthday. When Henry is 26, his cousin Albert (Allyn Joslyn) is engaged. Henry tells his mother he met a girl. Albert introduces his fiancée Martha Strabel (Gene Tierney), who is the girl Henry met. Henry waits on her at a bookstore and asks her to fly off with him. Albert complains about Martha sneezing during a concert, and she goes in the library, where Henry kisses her. Martha tells Henry that she is marrying Albert to leave Kansas. Henry says she will marry him and carries her away. Her father (Eugene Pallette) disinherits her.
Ten years later Henry has a son, and he gets a telegram that Martha left him. Grandpapa asks why. Strabel and his wife (Marjorie Main) quarrel over the Sunday funnies by way of a servant. Albert comes in and says he saw Martha on the train. She is allowed in and refuses to apologize but stays. Henry and Grandpapa look in the window. Albert tells Martha he is still willing to protect her. Henry and Martha quarrel, and he gives her an expensive bracelet. Martha is jealous and asks for a divorce. Grandpapa wants to take her back to New York. Martha realizes that her son is like Henry, and she runs off with him and Grandpapa.
Ten more years pass. Henry goes to the follies, sees Peggy Nash (Helene Reynolds), and meets her. She considers him too old, and he learns she is going with his son Jack. Peggy asks for $25,000, and he agrees. Henry tells Martha, but she knows about Peggy. Henry says he is lucky to have Martha. Jack Van Cleve (Tod Andrews) comes in and asks for $100. Henry mentions Peggy, and Jack says he tired of her. Jack says he met a showgirl from Philadelphia. Martha tells Henry that he has a tummy, and she is safe now. On their 25th anniversary Henry jealously questions Martha and learns she has been seeing a doctor. She dies that year. When Henry is 60, he asks for more money, and Jack warns him not to go out so much. Henry wants a girl to read to him. At 70 his medicine cabinet is full, and he dies happily attended by a beautiful nurse. After he finishes his story, His Excellency sends Henry up to be with those he made happy.
This sentimental comedy recalls an earlier era.