Bimbo prepares to rob a train that he has forced to stop. He then sings "The Holdup Rag." A ferocious bearded cowboy emerges, eats the barrel of Bimbo's gun, and, pulling off his beard and costume, reveals himself to in fact be his wife Dangerous Nan McGrew, whom he had abandoned. She then throws Bimbo into the locomotive, disconnects it from the rest of the train, and they drive off.

A Bouncing-Ball rendition of the title song features animated cats.

In a vaudeville act, Betty Boop (with dog's ears) sings "You're Drivin' Me Crazy;" Bimbo sneaks into the show and runs afoul of a stage hypnotist.

The surreal, nightmarish atmosphere of Bimbo's Initiation has made it one of the most renowned Fleischer Studios shorts. Bimbo is walking down the street when he suddenly disappears down an open manhole. He lands in an underground clubhouse of a secret society. The song Wanna Be A Member? is parody lyrics written to the 1919 song The Vamp (or Vamp A Little Lady).

A young dog calls on Betty but fraternity hazers kidnap him. With a Bouncing Ball, Rudy Vallee sings the title tune.

Betty Boop (with dog's ears) is moving; Bimbo comes with his moving van and is smitten with her. Songs: "Moving Day," "Hello Beautiful."

Bimbo's minding his baby brother, but neighbor Betty Boop (with dog's ears) wants him to come over and play.

Sun bonneted Betty Boop takes a train to "Rudy Valley" where she gains weight and Rudy Vallee performs the title song with Bouncing Ball.

Betty Boop is queen of the Masquerade Ball. She get annoyed by the king of the ball. Bimbo does Italian scatting to confuse the king. Bimbo and the king pull on Betty's arms. Her skirt goes up, showing her underwear and her two garters. But a little creature pins the dress. Then, Betty flips a coin to see if the king or Bimbo wins her affections, but doesn't really work. So the king and bimbo fight with wooden swords. Bimbo loses and is taken away by a knight, but Bimbo soon realizes it is Betty and asks him to marry her.

Bimbo climbs a beanstalk to find Betty Boop enslaved by the giant.

Betty Boop goes to Grandma's through the woods despite wolf warnings; but Bimbo follows and gives the old story a new twist.