I’ll bet most people on the Board won’t recognize Courageous Cat and Minute Mouse, which was a made-for-TV cartoon series from 1960. They live in the Cat Cave, travel in the Catmobile and the Catplane, and can be called by the Cat Signal searchlight. Instead of a Utility Belt with lots of gadgets, he has an apparently inexhaustable supply of themed “guns”. It’s very obviously a parody of Batman and Robin. What’s surprising is that it’s by Batman creator Bob Kane (plus Gerald Rappoport)
In 1967-8 Marvel comics had Not Brand Ecch, which ran parodies of their own superheroes (and DC ones, as well), written and drawn by the usual Marvel staff, often the very ones who wrote and drew the original characters. It ran 13 issues
After writing The Hobbit, Tolkien wrote Farmer Giles of Ham (although it wasn’t published for another dozen years). It’s been argued that this was a sort-of parody of The Hobbit and adventure tales in general, with Giles a reluctant hero who sort-of defeats a dragon with the aid of a named sword. There are a lot of scholarly in-jokes.
I have seen a lot of one-panel or one-page joke and parody strips by comic book artists (there’s a great drawing by one of the Superman artists showing Superman, carrying Clark Kent’s clothes, angrily banging on the door of a phone booth so he can get inside and change, but Alfred E. Neuman refuses to get off the phone), but I’m looking for a long story or sustained series.
I remember it quite well - the theme music is very much like that of “Peter Gunn” (and of course, since I saw Courageous Cat first, I thought Peter Gunn and Spyhunter (Spy Hunter - Wikipedia) were ripping off CC)
I liked the Inferior Five. They weren’t a direct parody of existing characters (as the Not Brand Ecch parodies were), but of the idea of superheroes and superhero teams. Joe Orlando, who drew them, had drawn plenty of heroes for DC.
I really like what Phil Foglio did with Inferior Five in his Angel and the Ape miniseries from 1991, but Foglio (who both wrote and drew the series) wasn’t parodying his own work.
E. Nelson Bridwell wrote a lot of superhero comics, and White Feather is a clear parody of Green Arrow. (And I also loved what Foglio did in Angel and the Ape.)
William Shatner clearly parodied his own image in Free Enterprise.
Ricky Gervais’s Extras was chock full of actors doing parodies of themselves (Ian McKellan is particularly notable), but only one of them per show.
I think Charlie Sheen’s character in Hot Shots: Part Deux is, to a considerable degree, a parody of his own character in Platoon. And his father’s (who has a cameo appearance) in Apocalypse Now.
Wong Kar-Wai directed a very arty wu xia film called Ashes of Time, based on the novel Legend of the Condor Heroes. The movie went over budget and the shoot went on beyond schedule. With Wong as executive producer, the studio banged out a mo lei tau parody of the same novel, starring the cast of Ashes (plus Joey Wong), that actually got released before Ashes of Time did.
The golden age Hong Kong film era produced a ton of parodies and knockoffs, with actors riffing on their own iconic roles, sequels turning into parodies of the original, and so on.
Part parody, part tribute, I suppose: An episode of Batman: The Animated Series featured a fictitious TV series about a superhero called “The Gray Ghost,” which Bruce Wayne supposedly watched when he was a kid. Today, the actor who played the Gray Ghost, having been hopelessly typecast and unable to get any other serious acting work, is now unemployed, mostly forgotten, and living in poverty.
That actor is voiced by Adam West, who of course had been hopelessly typecast and unable to get any other serious acting work after playing Batman.
Not sure if this counts (even though the OP was mine). There are several commercials starring people from James Bond that obviously parody the movies.
Daniel Craig vs James Bond ad for Heineken
Daniel Craig “The Chase” ad for Heineken. Craig spent a lot of time portraying a darker, craggier Bond, but in this he says he played a Roger Moore-style lighter Bond
Harold Sakata (Tosh Togo), who played Odd Job in Goldfinger appeared in a number of Vicks cough syrup ads as an unnamed martial arts expert who was clearly supposed to be Oddjob
If things like that count, then perhaps the numerous examples of celebrities appearing on Saturday Night Live (or other venues) in parodies of their own work would count.
Donald Westlake, under the pseudonym of Richard Stark, wrote grim, gritty, dark thrillers about a criminal who went only by the name of Parker. They were big hits and led to multiple movies.
Under his real name he wrote light comic caper tales.
One day he was writing a Parker book and it kept coming out funny. So he wrote it as a parody with a gang of incompetent crooks lead by John Dortmunder. That was such a hit that he dropped the Parker series and wrote about a dozen bestselling Dortmunder novels and led to multiple movies.
Neil Young’s then-band Buffalo Springfield’s song “Broken Arrow” starts off with a snippet of their own song “Mr Soul”, with screaming fans and over-the-top pretentious rocker scat singing added, which seems to me to qualify as a parody of it, or of themselves as a rock 'n roll phenomenon.
In The Cannonball Run, Roger Moore plays a character ostensibly named Seymour Goldfarb. His wealthy mother objects to his shunning his life as an heir to be a spy. He spends the whole film driving around in an Aston Martin with all the 007 secret modifications. He identifies himself to everyone else as Roger Moore. It’s unclear to me whether he is supposed to be: (1) a rich guy named Seymour Goldfarb pretending to be the famed actor, Roger Moore, (2) a rich guy named Seymour Goldfarb who is known to the world as the actor in spy films named “Roger Moore,” or (3) a spy named Seymour Goldfarb with the alias “Roger Moore” who superficially resembles the fictional character in our universe known as James Bond. In any event, I think this is supposed to be a parody of James Bond.