Auditioning actors for a 1 hour show recounting his thrilling life provokes many emotions in Jack: lust for a young actress, vanity when an elderly woman from his hometown shows up, and especially greed. A young actor is perfect for Jack as a child, which the actor's 10 year old agent takes every advantage of.
On the anniversary of Don Wilson's 27 years of service with Jack, he and Jack recall the first day they met, when Don showed up for an audition and Jack put him through dance and elocution classes to "whip him into shape".
Mamie Van Doren and Dennis Day sing a duet of "You Make Me Feel so Young." Later, they play the roles of a condemned prisoner's wife and son. Of course, Jack plays the condemned man, who is about to be executed.
Jack answers a reporter's questions in his dressing room, with Rochester to heckle him. In a flashback, we see some of Jack's childhood. In a well furnished Victorian home, Jack was a money hungry brat, and his father loved getting the family together to play their instruments together, despite his ineptness with a violin.
Jack refuses to leave a homeless shelter until they give him back an ancient jacket Rochester donated, which had $200 sewed in the lining. Jack's just returned from a desert hike with the Beverly Hills Beavers, so due to his dirty clothes & 3 day beard, everyone at the shelter believes he's an extraordinarily picky homeless person, not the most generous man in show business.
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 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.