The first time I read Tom Clancy’s novel Rainbow Six, I wondered if it was an intentional self-parody. I decided after reading the next two that it was unintentional.
In Weird Science, Vernon Wells plays a “mutant biker” who is clearly derived from, if not actually his “Wez” character from The Road Warrior.
The various Asgardian plays within the Thor movies
The Unbearable Weight of Massive Talent is basically a Nicolas Cage movie parodying Nicolas Cage. Cage also appears with Andy Samberg in his “Get in the Cage with Nick Cage” SNL segment (with Andy playing Cage and Cage playing “his identical in every way clone”).
In Jay and Silent Bob Strike Back, Matt Damon, Ben Affleck, Gus Van Sant, Wes Craven, Shannon Doherty, Jason Biggs, James Van Der Beek, Mark Hamill and others parody their films via references, quotes, or shooting entire scenes to fictitious sequels.
In one of Billy Joel’s live CDs, he’s performing his song I Go to Extremes. As he’s playing towards the end, he subs the line “I don’t know why I go to extremes” with “I don’t know why I go for ice cream.”
Sheen in Being John Malkovich parodies his own public image (at the time).
Cher spoofed herself in the 2003 film Stuck With You, co-starring Matt Damon and Greg Kinnear as a pair of conjoined twins.
In Mozart’s Don Giovanni, the titular character is being entertained by a group of musicians in his villa shortly before his demise. They play various popular opera numbers of the time, including a snippet from Mozart’s own aria Non più andrai. This is made even more amusing by Leporello’s subsequent quip : Questa poi la conosco pur troppo (“Now that tune I know too well”).
In The Beautiful and Damned, F. Scott Fitzgerald takes a dig at his first book:
“You know these new novels make me tired. My God! Everywhere I go some silly girl asks me if I’ve read ‘This Side of Paradise.’ Are our girls really like that? If it’s true to life, which I don’t believe, the next generation is going to the dogs. I’m sick of all this shoddy realism. I think there’s a place for the romanticist in literature.”
Now THAT’S a clever and unexpected self-own,
In one of the Warner Brothers Golddiggers films, Ruby Keeler auditions for a part and is turned down. The director who tells her “We can’t use you” is played by Busby Berkeley; Keeler was his big star.
Jack Sheldon sang “I’m Just a Bill” for Schoolhouse Rock (and was the voice of the bill).
Later he sang “The Amendment Song” in a classic Simpsons episode, parodying his earlier work.
A case could be made that most of Procol Harum’s output was a parody of their early work.
Jim Cummings reading the script for Star Wars in voices, with Winnie the Pooh as Darth Vader.
In John Updike’s Rabbit at Rest, the title character muses to himself after seeing the word “redux” in a newspaper headline:
He hates that word, you see it everywhere, and he doesn’t know how to pronounce it.
…the joke being that Updike himself had brought “that word” back into the mainstream when he used it in the title of Rabbit Redux.
Not to mention his appearance in Jay & Silent Bob Strike Back, which also features parodies from Jason Biggs, James Van Der Beek, Gus Van Zant, Shannen Doughtery, Ben Affleck and Matt Damon (though I think they were all mentioned previously).
Debbie Gibson and Tiffany were about the same age, became famous at about the same time, and their fans were in the same demographic. So naturally, the media assumed that they must be arch-enemies.
In 2011, they co-starred in a spectacularly bad TV movie called Mega Python vs. Gatoroid. The movie’s main selling point was a catfight between the two.