Chekhov's Gunman

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Top Ten Actors Playing Themselves- A Mexican Standoff

There seems to be something freeing about an actor portraying themselves. Sometimes it allows them to create a neat little sub-character out of themselves. The best example of this is Carl Weathers’ incredibly frugal turn as Carl Weathers on Arrested Development. Also of note is Bill Murray in Zombieland, which is a twist that was spoiled for me so now I’m spoiling it here for anyone who hasn’t seen it. Oh, vengeance is sweet.

There’s also the very fun incarnation of this where a celebrity gets a rare chance to subvert their public persona for laughs. Ricky Gervais has basically made a career out of this, on shows like Extras, giving us scenes that delight us with giddy glee, like Daniel Radcliffe unfurling a massive roll of condoms clad in a boyscout uniform, which is, admittedly, exactly what anyone would carry around if they were Harry Potter.

Unfortunately, that Extras shoutout means it won’t be showing up on this list, but I hope I’ve assembled enough good stuff here to still make it worthwhile.

Tobey Maguire Tropic Thunder

10.)    Tobey Maguire, Tropic Thunder

Tobey’s is the shortest cameo on this list, but since it absolutely never ceases to make me laugh, I’m going to go ahead and give it a slot here. Pleasantville himself shows up in one of the film’s many fake trailers, this one called “Satan’s Alley.” Seabiscuit plays himself as a monk, engaging in a sordid homosexual affair with Robert Downey, Jr.’s method actor Kirk Lazarus, straight out of some weird parallel universe where Spider-Man and Iron Man rub each other’s prayer beads.

Luis Guzman Community

9.)    Luis Guzman, Community

Luiz Guzman is the most notable graduate of Greendale Community College, located somewhere in the state of Colorado. There is a statue erected in his honor on campus. And his return to campus has as much pomp and circumstance as you might expect. When Dean Pelton (Jim Rash) discovers that Guzman is available to film a commercial for the school, he turns the project into an Apocalypse Now!-level debacle, going far over budget and traumatizing many of his crew. By the time Guzman arrives, the school is in chaos. Luckily, the Carlito’s Way veteran is there to give a Jeff Winger-level pep talk to the struggling Dean.

David Bowie Zoolander Walk Off

8.)    David Bowie, Zoolander

Bowie benefits from showing up during the best scene in the movie. Surprisingly-competent character actor Bowie shows up where he is needed most, which is apparently when someone is needed to judge a male modeling “walk off” competition. David’s reactions provide many of the scene’s big laughs, and add to the sequence’s already strange tension. Also, if you haven’t seen Bowie as Tesla in The Prestige, do so, because it’s pretty much the best movie Christopher Nolan has ever made.

The Simpsons The Rolling Stones

7.)    Oooohhhh God, uh…. er… how do I pick just one Simpsons cameo….? Oh, okay, The Rolling Stones, The Simpsons

It’s really hard to pick just one. This spot could just as easily have gone to so many other people, including a Beatle or two, but since the Stones were the first to come to my mind when picking this slot, I suppose the honors should be bestowed upon them. The Stones host a very funny Rock and Roll Fantasy Camp that Homer attends, to be rewarded by Homer trying to take over one of their live shows and having to fight him in a giant, pyro-capable Devil head.

FUN FACT: If I hadn’t given this to the Stones, the runners up would actually have been N*Sync…

Emma Watson This is the End

6.)    Michael Cera and Emma Watson, This is the End

Now I haven’t seen This is the End just yet, but the trailer alone is cause enough to throw these two up on here. In a film absolutely stuffed with celebrities portraying themselves, I’m going to give the early awards to these two. Cera gets to have fun and run around blowing cocaine in people’s faces, as Michael Cera is wont to do. And Watson, dear, sweet Watson, gets to rob the absolutely shit out of Seth Rogen and company, providing what I’m sure will be a wealth of typecasting where she waves axes at Danny McBride.

Futurama Star Trek

5.)    The Cast of Star Trek: The Original Series, Futurama

I love how ready these guys are to poke fun at themselves. In the ultimate take-off on crazy fans, the jarred heads of most of the cast of TOS are held captive by a crazed and hyper-intelligent being. At least until Fry challenges him to a trivia contest. You can find this strange episode in all of its glory on Netflix.

EDITOR’S NOTE: This would have gone to the Harlem Globetrotters, who appear in my favorite Futurama episode of all time, but unfortunately none of those guys were actually Globetrotters, so I must go weap at the fruitlessness of my life.

Michael Jordan Space Jam

4.)    Michael Jordan, Space Jam

“Actor” is a bit of a stretch here, but I don’t think anyone embraced the ‘playing himself’ idea quite so fervently as Michael Jordan, right ahead of special and surprise guest star Bill Murray who shows up to play basketball for little-to-no given reason in the film’s climax. His dramatic half-court arm stretching routine is one of the images from my childhood forever burned into my psyche, and has really informed the way I approach close, personal relationships.

Liam Neeson Life's Too Short

3.)    Liam Neeson, Life’s Too Short

Nothing I write here can do this justice. Watch it. It may be the funniest thing you see this month.

Andy Richter Arrested Development Brothers

2.)    Andy Richter, Arrested Development

Richter is blessed with the added benefit of not only portraying himself, but also the four other, little-known Richter brothers, each with their own unique personality and way of dealing with the Bluth family’s crap. Appearing in such diverse places throughout the show as Maeby’s teacher many times over and in Tobias’ most-likely ill-fated Fantastic 4 musical, Richter created an entire mythos around the brothers and how they all pretty much hate Andy.

Neil Patrick Harris Harold and Kumar

1.)    Neil Patrick Harris, the Harold and Kumar franchise

The cameo that saved a career. Harris had been out of the spotlight for a long time when writers Jon Hurwitz and Hayden Schlossberg decided to write Harris into their script for a surprisingly race-conscious stoner movie. Not only did this give us a great running joke through the surprisingly longevity-having franchise, but Harris’ portrayal of himself is also what netted him the role of Barney Stinson on How I Met Your Mother, propelling him to everyone’s go-to host of any awards show and absolutely all over our media, from projects as wide-ranging as Smurfs sequels and Dr. Horrible’s Sing-Along Blog.

Chekhov’s Gunman is a film and television blog moderated by Kevin Lanigan, a future writer of movies and TV and current writer of fan letters to Ringo Starr. Be sure to check back for coverage of Community and Game of Thrones, and whatever TV and movies have to offer. We also have weekly installments of these Mexican Standoffs and some Good Stuff.

Be sure to follow Kevin on Twitter, as he’s alright at it when he wants to be.

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