A cartoonist and his father woo two women in the family the comics satirize.
Jim Crocker Jr. (Robert Montgomery) is awakened by his butler Bailiss (Eric Blore), and his father James Crocker (Frank Morgan) tells him he wants to marry Eugenia, whom he just met; but her sister disapproves of actors. Jim gets drunk with Macon (Robert Benchley), meets Ann Chester (Madge Evans) and dances with her; but she goes with Lord Frederick Priory (Ralph Forbes). Nesta Pett (Cora Witherspoon) learns from James Crocker that Jim is a cartoonist. Jim comes in and is delighted to meet Eugenia (Billie Burke). The London Gossip editor fires Piccadilly Jim. James Crocker complains that Eugenia went to the Riviera, and Jim can't find Ann. Jim creates the Richswitch family comic strip.
When Nesta, her husband Herbert Pett (Grant Mitchell), Eugenia, and Ann return, Priory shows them the cartoons. Nesta blames Eugenia, who faints. Jim learns that Ann is Nesta's niece, and Nesta tells Eugenia not to see James. Herbert says everyone laughs at him, but he got boat tickets to America. Jim runs after Ann and tells her he is Bailiss and will get Piccadilly Jim to stop the cartoons. Jim takes Ann to a tea garden and pays the driver to delay so that Ann will miss the boat. Ann calls Nesta, and Priory offers to bring her on the next ship. James, disguised as Count Olaf Osric, shows who he is to Eugenia and sails with them. The editor tells Jim the comic strip would continue without him. Jim calls Ann, who says she is sailing. So Jim tells Bailiss they are sailing as father and son.
On the ship Priory tells Ann he is worried he won't measure up; but Jim tells her they have electricity. Ann wants Jim to meet her family at the dock. Nesta identifies Bailiss as Jim's butler. James tells Jim he is a house-guest with the Pett family. Before Jim can tell Ann the truth, she learns he is the cartoonist; she despises him and leaves. Jim makes the caricatures more kind; but his gifts to Ann are returned. Bailiss shows Jim that Ann and Priory are to wed and says Priory is not a real lord. Jim calls on Nesta, who thanks him for her fame and goes off to be on the radio. Jim tells Ann that she is in love with him, not Priory. At dinner with the family Jim starts to unmask himself, stimulating James to remove his disguise. Nesta is upset but relents on his marrying Eugenia. Bailiss tells Jim that Priory is a lord. Jim tells them he is sailing and tells Ann he was wrong about Priory. He kisses the bride and goes. Bailiss tells Jim not to give up. Jim runs down the gangplank to Ann, and they kiss.
A charming and persistent American wins out over a complacent British lord despite the obstacles and his deceptions.