In some ways, I think it takes more courage to play yourself on The Simpsons than just to do a cameo as someone else. After all, most of the people listed below are pretty mercilessly skewered on the show, but it’s all in good fun. These are my favorite cameos by people playing themselves.
10. Neil Patrick Harris
Neil Patrick Harris has only one scene in the episode that he appears in. He plays Bart in a TV movie based on his exploits with the mob called “Blood on the Blackboard”. Years before Harold and Kumar came out; The Simpsons showed that Harris was more than willing to poke fun at himself, playing himself as a cheesy TV actor. Great work.
9. Leonard Nimoy
I
n the classic episode “Marge vs. the Monorail”, Nimoy shows up as the “celebrity” for the maiden voyage of the new train system. Nimoy doesn’t do much in the episode, he just kind of sits back and observes the action, that is until his brilliant final scene where he says “My work is done here”, before some kid tells him he didn’t do anything. “Didn’t it?” Nimoy quips before fading out in Star Trek homage. Great.
8. Mickey Rooney
In the episode “Radioactive Man”, Milhous gets cast as sidekick, Fallout Boy, but cannot handle the pressure of being a star. The studio brings in Mickey Rooney to try and coach Milhous. Rooney is hilarious, first as he goes over his resume as a child star and the biggest box office drawn from 1939-1940 (“Spanning two decades!”), and then when he dons the Fallout Boy costume himself, and finally as he is whisked away on a helicopter to help a little girl in a jello pudding commercial. Rooney, like all of the great Simpsons guest stars, pokes fun at himself wonderfully, and is hilarious to boot.
7. Dennis Franz
Dennis Franz willingly pokes fun at himself in the classic episode “Homer Badman” where Homer is accused of sexual harassment. Franz plays Homer in a TV movie (much like Neil Patrick Harris played Bart), as a psychopath who runs over cats on purpose, and lavishly leers at the pretty young babysitter. It took guts to admit that you are probably the perfect choice to play someone like Homer, but Franz pulled it off brilliantly.
6. Betty White
Betty White is hilarious in the episode Missionary Impossible, as the host of a PBS pledge show who keeps interrupting Homer’s favorite show to beg for money. My favorite line “If you watch even one minute of PBS and don’t donate, you’re nothing but a thief. A dirty rotten thief”, before chasing down Homer (along with the Teletubbies) to get him to make good on his donation. Betty White always seemed like such a sweet old lady, but here she brilliantly skewers her own image.
5. Jim Jarmusch
Full marks go to the producers for even thinking of Jim Jarmusch for the Sundance episode, a late run highlight for the show. When Lisa makes a documentary that becomes a big hit at Sundance, but hurts her family, Jarmusch walks her through life on the independent film circuit. He is full of great lines and moments, my favorite being as he talks during Nelson’s movie much to the annoyance of everyone around him, or when he literally fades out at the end of his performance. Perhaps Jarmusch should cast himself in one of his movies.
4. Mel Gibson
If Gibson did a role on The Simpsons now, it would have to be very different as at this point not everybody loves him anymore. But when he did the role, everyone did, and Gibson played brilliantly off of his nice guy image. His Mr. Smith Goes to Washington remake is classic, especially once Homer gets his hands on it – “All in favor, say die!” Gibson is funny and charming, and certainly willing to poke fun at himself, which is what was needed from him in this episode.
3. James Woods
James Woods shows up in Springfield to research a new role as “tightly wound convenience store clerk” and takes over for Apu. Years before he would overstay his welcome on Family Guy, Woods’ brilliantly played off his insane image, swearing at cheese while scraping it out, and arguing with Jimbo “Don’t mess me around, fella”, before being involved in a robbery. Woods set the standard for all the movie stars to cameo on the Simpsons in later years.
2. Mark Hamill
Mark Hamill initially did not want to be on the show, as he felt that making fun of Star Wars they way they did would be disrespectful. But, lucky for us, he changed his mind. His brilliant performance in Guys and Dolls, where he sings “Luke Be a Jedi Tonight”, and gets made when someone tries to upstage him (“It’s my face on the poster next to the steak, and you don’t you forget it”) or complaining that George Lucas makes him pay for the light sabers, Hamill brilliantly plays himself, and probably looks the most ridiculous of anyone on this list – except for the next guy.
1. Ron Howard
I don’t know why Ron Howard being so funny surprises me – after all he is the star of two of the most sitcoms in history, and his brilliant voiceover work on Arrested Development helped make that show great. But it’s his work as himself on The Simpsons where Howard truly outdoes himself in terms of hilarity. Playing a drunken version of himself, always in a bathrobe and saying that Homer’s new drink, The Lawnmower (which is wheat grass and vodka) sounds great, Howard is hilarious. In his first appearance, he outshines Alec Baldwin and Kim Basinger (which is why they aren’t on the list), and I can never help but laugh when he tries to make the jump from the SUV to home’s RV, and fails miserably. Howard is hilarious, and the best cameo a celebrity ever made playing himself on the show.
10. Neil Patrick Harris
Neil Patrick Harris has only one scene in the episode that he appears in. He plays Bart in a TV movie based on his exploits with the mob called “Blood on the Blackboard”. Years before Harold and Kumar came out; The Simpsons showed that Harris was more than willing to poke fun at himself, playing himself as a cheesy TV actor. Great work.9. Leonard Nimoy
I
n the classic episode “Marge vs. the Monorail”, Nimoy shows up as the “celebrity” for the maiden voyage of the new train system. Nimoy doesn’t do much in the episode, he just kind of sits back and observes the action, that is until his brilliant final scene where he says “My work is done here”, before some kid tells him he didn’t do anything. “Didn’t it?” Nimoy quips before fading out in Star Trek homage. Great.8. Mickey Rooney
In the episode “Radioactive Man”, Milhous gets cast as sidekick, Fallout Boy, but cannot handle the pressure of being a star. The studio brings in Mickey Rooney to try and coach Milhous. Rooney is hilarious, first as he goes over his resume as a child star and the biggest box office drawn from 1939-1940 (“Spanning two decades!”), and then when he dons the Fallout Boy costume himself, and finally as he is whisked away on a helicopter to help a little girl in a jello pudding commercial. Rooney, like all of the great Simpsons guest stars, pokes fun at himself wonderfully, and is hilarious to boot.7. Dennis Franz
Dennis Franz willingly pokes fun at himself in the classic episode “Homer Badman” where Homer is accused of sexual harassment. Franz plays Homer in a TV movie (much like Neil Patrick Harris played Bart), as a psychopath who runs over cats on purpose, and lavishly leers at the pretty young babysitter. It took guts to admit that you are probably the perfect choice to play someone like Homer, but Franz pulled it off brilliantly.6. Betty White
Betty White is hilarious in the episode Missionary Impossible, as the host of a PBS pledge show who keeps interrupting Homer’s favorite show to beg for money. My favorite line “If you watch even one minute of PBS and don’t donate, you’re nothing but a thief. A dirty rotten thief”, before chasing down Homer (along with the Teletubbies) to get him to make good on his donation. Betty White always seemed like such a sweet old lady, but here she brilliantly skewers her own image.5. Jim Jarmusch
Full marks go to the producers for even thinking of Jim Jarmusch for the Sundance episode, a late run highlight for the show. When Lisa makes a documentary that becomes a big hit at Sundance, but hurts her family, Jarmusch walks her through life on the independent film circuit. He is full of great lines and moments, my favorite being as he talks during Nelson’s movie much to the annoyance of everyone around him, or when he literally fades out at the end of his performance. Perhaps Jarmusch should cast himself in one of his movies.4. Mel Gibson
If Gibson did a role on The Simpsons now, it would have to be very different as at this point not everybody loves him anymore. But when he did the role, everyone did, and Gibson played brilliantly off of his nice guy image. His Mr. Smith Goes to Washington remake is classic, especially once Homer gets his hands on it – “All in favor, say die!” Gibson is funny and charming, and certainly willing to poke fun at himself, which is what was needed from him in this episode.3. James Woods
James Woods shows up in Springfield to research a new role as “tightly wound convenience store clerk” and takes over for Apu. Years before he would overstay his welcome on Family Guy, Woods’ brilliantly played off his insane image, swearing at cheese while scraping it out, and arguing with Jimbo “Don’t mess me around, fella”, before being involved in a robbery. Woods set the standard for all the movie stars to cameo on the Simpsons in later years.2. Mark Hamill
Mark Hamill initially did not want to be on the show, as he felt that making fun of Star Wars they way they did would be disrespectful. But, lucky for us, he changed his mind. His brilliant performance in Guys and Dolls, where he sings “Luke Be a Jedi Tonight”, and gets made when someone tries to upstage him (“It’s my face on the poster next to the steak, and you don’t you forget it”) or complaining that George Lucas makes him pay for the light sabers, Hamill brilliantly plays himself, and probably looks the most ridiculous of anyone on this list – except for the next guy.1. Ron Howard
I don’t know why Ron Howard being so funny surprises me – after all he is the star of two of the most sitcoms in history, and his brilliant voiceover work on Arrested Development helped make that show great. But it’s his work as himself on The Simpsons where Howard truly outdoes himself in terms of hilarity. Playing a drunken version of himself, always in a bathrobe and saying that Homer’s new drink, The Lawnmower (which is wheat grass and vodka) sounds great, Howard is hilarious. In his first appearance, he outshines Alec Baldwin and Kim Basinger (which is why they aren’t on the list), and I can never help but laugh when he tries to make the jump from the SUV to home’s RV, and fails miserably. Howard is hilarious, and the best cameo a celebrity ever made playing himself on the show. 
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