Gleason stars as retired gangster "Tough Tony" Banks (no relation), whose old boss, a mob leader named "God" (Marx), wants him to kill imprisoned stoolpigeon George "Blue Chips" Packard (Rooney). Meanwhile, Tony's daughter Darlene (Alexandra Hay) has joined a group of hippies who are being hassled by the police, so Tony's flighty wife Flo (Carol Channing) invites them all to live at the Banks house. Tony infiltrates Packard's prison, but decides not to go through with the hit after an accidental LSD trip enlightens him. God is not happy to hear this, so he takes Darlene hostage on his luxury yacht to force Tony's hand. Flo and Darlene's hippie friends go on a rescue mission, while Tony escapes from prison by dosing the inmates, the warden (Burgess Meredith) and a visiting senator (Peter Lawford) with LSD and flying off in a balloon made of garbage. What can we say? It was The '60s.
This film contains examples of:
- Celebrity Paradox: In the opening scene, Tony is wanting to watch In Harm's Way on television. Not only was it an Otto Preminger film, but it also featured Burgess Meredith as a cast member.
- Creative Closing Credits / Credits Gag: All the closing credits are sung by Harry Nilsson, even the copyright information! ("Copyright M-C-M-L-X-V-I-I-I by Sigma Productions Incorporated — your seat's on fire.")
- Culture Clash: The point of the film is to satirize The Generation Gap of the late 60s through the interaction of the hippies and the gangsters.
- Dirty Old Man: God tries to make out with Darlene, but she's having none of it.
- The Don: God.
- Feng Schwing: The bachelor pad that Angie (Frankie Avalon's character) lives in.
- Get into Jail Free: In order to get at Blue Chips, Tony has to get himself thrown in jail.
- I Have Your Wife: Darlene goes to see God to talk him into leaving her father alone. Instead, he kidnaps her to force Tony to go through with the job.
- Marijuana Is LSD: Uniquely reversed. The film's climax involves spiking the food supply of a prison with LSD as part of an escape plan. However, Groucho Marx was the only member of the cast or crew who had actually had any experience with the drug, and he wasn't anywhere near that sequence. So, lacking any sort of direction, everyone settled for either acting drunk, or trying to compensate with volume. How they got Timothy Leary to endorse that is a mystery.
- One Last Job: God wants Tony Banks to do a hit on "Blue Chips" Packard.
- Pop-Star Composer: Harry Nilsson did the score and contributed some songs, most famously "The Cast & Crew", which is all of the film's credits set to music.
- Terrified of Germs: God, so much so that Darlene escapes his clutches by threatening to kiss him on the lips.