Jack's guest is laid-back singer Andy Williams, which prompts a visit from Jack's Pasadena Fan Club President (Madge Blake, Aunt Harriett on "Batman"), who can't believe Really Old Blue Eyes would book another blue-eyed guest. Jack lectures Andy to work harder to promote his career, so Andy changes from a sweater to a tux to join Jack at a premiere - which turns out to be a meat market opening. When a customer (Lee Meriwether, Catwoman in the Batman (1966) movie) gushes over Andy's crooning, he's too embarrassed to admit who he is.
Jack proposes recording a lucrative comedy album with Bob Hope, upon finding out how worthless his investments are: as chief stockholder of a harpoon company, Jack gets dubbed Schnook of the South. Fretting that he won't be able to counter Hope's hilarious ad libs, Jack orders his writers to give him all the laughs, but Old Ski Nose is too slick to fall for that.
Jack affronts guest Connie Francis by claiming comedy is hard, but singing easy, then sics his apprentice announcer Harlow Wilson, a devoted fan of pop singer Connie, on her. The cast lampoons "The Beverly Hillbillies" in a musical sketch with Connie as Jack's wife, and Harlow in the Jethro role.
The Smother Brothers confound every attempt by Jack to force them into his straitjacket comedy formula while performing his theme song, but even scarier to Jack is when he's pinned under an unexploded bomb in a World War II London air raid. The UXB squad turns out to be the Smothers. Tom can't remember which wire to pull, while Dick uses the opportunity of Jack being immobilized to lock in an appearance on Jack's final program.