Jack goes on trial for murder, defended by superstar lawyer Perry Mason (Raymond Burr). The women in the courtroom swoon over Perry, but his defense of Jack is feeble. When Jack asks how Perry always wins on his own show, Perry Mason sneers "because my writers are better than yours !"
Jack has four tickets to a new play. He and his new girlfriend were originally going to go with Don Wilson and his wife, but Don called to cancel. Jack's girlfriend gets him to call and invite Jimmy and Gloria Stewart. Jimmy accepts the invitation thinking he's talking to Jack Lemon. He and Gloria panic when they realize that it's Jack Benny instead.
Jack tries to wow guest songstress Jane Morgan by taking her to - a cafeteria? That's bad enough, but for Jack it's a war zone, with hostile attendants & personalized land mines at each counter awaiting their pickiest, least favorite diner. Will the hash slingers go easier on finicky Jack because he's with beautiful, blonde Jane?
Near the end of a new year's eve interview with a female reporter, Jack tells her the tale of that same night in 1953, when his plans for the evening did not go as expected. Leaving him with no one to be with at midnight and personal regrets.
Jack and Gisele are returning from a show in Phoenix and get lost. They stumble into a café in what appears to be a Western ghost town and ask directions. While they sup on peanut butter sandwiches, the owner spins a story from the town's history, where a black-hearted villain called Tombstone Harry tries to force a beautiful saloon girl to marry him, or he'll foreclose on her mortgage. A black-garbed hero, the Cactus Kid, attempts to stop the villain.
In this episode, Jack becomes aware of the high cost of low cost traveling. Indeed Jack's stinginess made him opt for a cut-rate airline and ... for trouble! The pilot is crazy, the plane lands on a meadow instead of an airport, and the farmer owning the pasture end the baggage handler are pains in the neck! Of course, Jack arrives late for the show and Dennis has already taken it over!
Jack's all excited because he's going to make his first film in many years, directed by Billy Wilder. It's supposed to be a secret yet he calls Hedda Hopper and Louella Parsons right away, and soon even the mailman and a house painter know. Dennis comes over in a raincoat that Jack talks him out of. When Wilder arrives he's not too keen on the whole movie project.
Jack tries to trick Mickey Rooney into appearing for free as a guest star on his show. Jack and Mickey are in a sketch depicting a prison in the future year 1985, wherein all the prisoners are pampered.