Jack's guest is British comedian/singer Max Bygraves. After Jack claims to have discovered Max and introduced him to U.S. audiences, there's a flashback to Jack first seeing Max perform in London. Jack loves Max's performance, but is aghast with Max's dead-on impersonation of Jack.
Jack is thrilled to introduce his guest, actor Peter Lorre, who seems very modest and timid - until Jack congratulates him on his ability to personify evil, spurring Lorre to pull a knife from his jacket pocket. Jack has a nightmare involving Lorre, in which Jack visits a new doctor, because the doctor takes coupons and validates parking. Also waiting for the doctor is Lorre, hiding behind a newspaper blaring the headline "Fiendish Murderer Escapes."
Having Martha Tilton as a guest causes him to reminisce about when they worked together with the USO during World War Two, on the island of New Guinea. During the show, Jack performs his stand-up, then starts playing his violin, when the sirens sound and enemy planes start bombing, everyone runs off but jack keeps playing. Eventually two Japanese soldiers, all that's left after a hari-kiri wave, surrender if he'll stop playing.
For a change of pace, Jack does a plot-less revue instead of a scripted play, by supposedly responding to questions culled from fan mail. The acts include an over the top radio sound effects man, Don and Dennis impersonate Laurel and Hardy repairing a Model T tire, and Jack playing his violin with an eccentric pianist accompanying.
Jack sups at a chichi nightclub where heartthrob crooner Robert Goulet is dining. Will Goulet pilfer Jack's drop-dead gorgeous date or will the sex symbol comic pull women away from Goulet? Two versions are presented. Which one is true?
Jack's guest is 6'6" Western star Clint Walker, who sings a song and banters with Jack. Jack is insulted when the gigantic Walker snubs Jack's suggestion that he play Clint's brother in a movie. But Jack auditions for the part anyway.
After Don does a man on the street interview that ends badly, Jack brings out Johnny Carson then into his first year as "Tonight" host. Carson displays samples of his various talents, including singing, drum playing and card tricks. He then does an interview with Jack where private thoughts can be heard "Strange Interlude"-style.
Ed Sullivan is nervous about doing "His first Dramatic part" on the show, but he gets into the spirit playing an attorney defending a French girl accused of murder. The case seems to be stacked against district attorney Jack when the entire jury are beret-and-smock wearing,baguette-wielding Frenchmen.
Hawaiians are thrilled to sing Aloha to stingy Jack Benny, who gets only 1 lei, while a fellow passenger is covered with them. The romantic atmosphere of the Pacific cruise back to L.A. overwhelms Jack, who envisions a zoftig blonde passenger as Jayne Mansfield. Jayne breathes "You're Just Too Marvelous," to love-struck Jack.