One of the things I loved about the old Mad Magazine, especially in the 1960s, was the way they’d do a “parody” of a movie that didn’t actually exist. But it played off familar cliches, or off a real movie. But they gave it an original cast of famous people, usually drawn by Mort Drucker, their master caricaturist.
Some examples:
Son of Mighty Joe Kong – sort-of parody of the RKO “Ape Trilogy” of King Kong, Son of Kong, and Mighty Joe Young, starring Dick van Dyke, James Garner, and Doris Day. It ends up with Doris Day atop the Empire State Building. Appeared in 1965, which featured a cover painting of gorillas in biplanes trying to shoot a giant Alfred E. Neuman off the Empire State Building, appropriately enough. New York station WWOR was famous for showing the Ape Trilogy on Thanksgiving morning against the fasmous parades on the other networks, but this parody predated that.
The Flying Ace starring the Beatles as WWII pilots, Ed Sullivan as their commanding officer, and Natalie Wood as Ringo’s character’s wife. Also appeared in 1965
My Fair Ad-Man a musical parody, using the songs and outline from Lerner and Loew’s My Fair Lady to tell the story of two advertising executives – Cary Grant and Charles Laughton – who make a bet that Grant’s character can turn a beatnik (Frank Sinatra, with a beret and goatee) into an advertising executive. Features Dean Martin as a singing policeman. From 1960
The Guru of Ours – sort-of parody of The Wizard of Oz, but really parodies modern trends. With Liza Minelli in the Dorothy role (she was Judy Garland’s daughter, of course, and would go on to play Dorothy in the 19754 animated Journey Back to Oz) and Tiny Tim as Aunt Em, Ed Sullivan (again) as the Guru, with what look like George Hamilton and Michael J. Pollard in other roles
Antenna on the Roof – instead of directly parodying the movie, they did this indirect parody of modern trends, with Zero Mostel (who originated the role of Tevye on Broadway) oin the Tevye part. I recognize Woody Allen as one of the suitors, but can’t recall any other obvious caricatures. From 1972
Most other parodies don’t quite fit this mold. I don’t recall celebrity caricatures in 1965’s Crazy Fists (boxing movie parody. 007: The James Bomb Musical deserves to be better known (especially with its “title song” 007, sung to the tune of “Oklahoma!”, or with its parody of S.P.E.C.T.R.E. – “I.C.E.C.U.B.E.”, The International Conspiracy to Eliminate, Contaminate, and Undermine the British Empire), but it only had caricatures of Sean Connery and Bernard Lee (and Mike Hammer), so It’s not really the same thing. There were movie parodies in several of the Mad paperbacks, rather than the magazines, including one with Marlon Brando playing Tarzan. And, of course, there were the political musical parodies, but in those the caricatures were of the people actually portrayed.