George Clooney as a special guest star on South Park. He voiced Stan’s gay dog Sparky, his voice work was dog barks.
And of course he played the ER doctor in the South Park movie.
Another, and my favorite, Matt Damon story: I think it was when he was on the talk show circuit promoting Invictus. The host complimented him on staying so fit and he confessed that he’s a lazy, weight gaining schlub between projects. The story he told went something to the effect of:
“I noticed my suits were starting to not fit right and I told my wife I thought George had hired someone to break in and alter them. She said, “Maybe you’ve just put on some weight?” (Forehead slap) Apparently I’m so vain and stupid it was easier for me to create this elaborate conspiracy involving Clooney and a ninja tailor than to realize I might want to back off the Twinkies a little.”
James Woods also spoofed himself on The Simpsons, in which he was an actor so Type A, obsessive, and method, he worked at Apu’s Quickie Mart before playing a convenience store clerk.
Kanye West at least claimed to have found the New Yorker cartoons/Kanye Twitter mashups phenomenon funny. In any event, it hasn’t hampered his exuberant Tweeting his fans in his inimitable style.
The British rock band Muse is completely self-aware and vocal about the frivolous and more over-the-top aspects to their music and concerts. They also regularly Tweet unflattering and sometimes downright silly pics of themselves, knowing that the mocking returns include not just fan reactions on Twitter, but photo manipulations in the lolz thread on their website. On one memorable occasion (the “Snuggie” box incident), they posted self-made lolzes to the lolz thread.
Hugh Laurie and Hugh Grant are a couple of British examples. Something about the name Hugh, perhaps?
To be fair, that sounds like something George Clooney would do.
Matt Damon played himself in Team America. I don’t think it gets any better than protraying YOURSELF as a retard…
Michael Caine is honest about being a hack.
He admits to selecting all of his movie roles based on location at a particular season. That’s it. No script required.