3. Jean-Claude Van Damme, JCVD
The last thing anyone expected from the star of Timecop was subtlety and nuance, but that’s exactly what Jean-Claude Van Damme delivers in JCVD, a fascinating blend of truth and fiction that’s both a triumphant comeback and an excoriating admission of personal failure. Van Damme strips away all his “Muscles From Brussels” vanity to play a washed-up version of himself that’s uncomfortably close to the truth: relegated to potboiler knock-offs of his former successes, estranged from his family due to nonstop shooting schedules, and recognized solely by an older, diminishing fan base that still ranks him as an also-ran to Arnold Schwarzenegger and Sly Stallone, even in his own hometown. But ironically for a guy who made his name by delivering high-kicks to the face, this painfully vulnerable side makes for Van Damme's strongest performance yet. After all, it takes real balls to admit that most producers would pass him over for his old rival Steven Seagal, if only Seagal were willing to lose the ponytail.


4. Wayne Brady, Chappelle’s Show
In a bid to play against his public persona—the whitest, safest black man in show business—Wayne Brady appeared in an incredible seven-minute skit on Chappelle’s Show, whose Paul Mooney had accused him of making “Bryant Gumbel look like Malcolm X.” In the skit, Brady drives Chappelle around, stopping to do a drive-by, kill a cop, and in the most hilarious, oft-quoted moment, collect money from his stable of prostitutes. And with these nine words, Brady proved himself self-aware and gloriously in on the joke: “Is Wayne Brady gonna have to choke a bitch?”


5. Bob Barker, Happy Gilmore
When he’s paired up with super-goof Adam Sandler in a pro-am golf tournament, Bob Barker loses his cool, dissing Sandler’s playing and ending up in a drawn-out fistfight with him. The sweet, demure Barker—a spokesman for spaying and neutering your pets!—ends up kicking the shit out of Sandler up and down the golf course, ending the scene by calling him a bitch. That isn’t the guy from The Price Is Right!

6. Topher Grace, Oceans Eleven and Ocean’s Thirteen 
Topher Grace plays himself as a callow, mildly annoying Hollywood pretty boy hoping to pick up some scuzzy credibility from Brad Pitt’s master criminal/part-time poker tutor in Oceans Eleven, his second collaboration with Traffic director Steven Soderbergh. He returned in Ocean’s Thirteen, at which point seemingly half the plot seemed to consist of actors spoofing their public image—including Bruce Willis and Julia Roberts, who appears as both George Clooney’s girlfriend and as herself, in a self-indulgent dual role.


7-9. Carl Weathers, Judge Reinhold, and Andy Richter, Arrested Development
Arrested Development is a madcap, zany take on corporate corruption and sitcom dysfunctional families, so it follows that its trio of memorable self-deprecating cameos are just as nutty. In the third season, Conan O’Brien wingman Andy Richter made an appearance spoofing his short-lived Fox show Quintuplets by playing five identical brothers with starkly different personalities. (For instance, sensitive Donnie Richter thinks, “Andy’s an attention hog, can’t seem to find an audience, but I love the fat SOB anyway.”) The “real” Andy appears only briefly in that episode, acting like a big shot and only agreeing to appear at a charity event upon hearing there will be a free dinner. Judge Reinhold plays a similarly stuck-up spin on himself, indignant that playing a TV judge means wearing a robe obscuring all the weight he lost for the role. But the gold standard of self-deprecating Arrested Development cameos is unquestionably Carl Weathers. The Predator co-star plays an obsessively stingy version of himself; his only goal when acting is to not touch his per diem, and to “get a stew on” with food swiped from craft services. His cheapness knows no bounds, whether he’s boasting about the “loophole the wrong guy discovered” in milking cash from airlines by intentionally getting bumped from flights, or merely conning Burger King into giving him a free refill of any drink he wants, not just the one he ordered.

10. John Malkovich, Being John Malkovich
The screenwriting debut of Charlie Kaufman and directorial debut of Spike Jonze is agreeably loopy and twisted, as a nebbishy nobody and his scheming co-worker discover a portal into the mind of actor John Malkovich, and start charging people to make the trip and live out a little piece of Malkovich’s life. But the whole project just wouldn’t be nearly the same without Malkovich playing himself. The script calls for a fey, temperamental, self-absorbed Malkovich, and the real one complies, playing the role to the hilt; reportedly Jonze and Kaufman spent years persuading him to take the role on after he refused several times. It was well worth the effort.

11. Paul Giamatti, Cold Souls
It takes real chutzpah to make a metaphysical comedy with a conceit so obviously indebted to Being John Malkovich, and Sophie Barthes’ Cold Souls falls well short of its ambition. But Paul Giamatti’s take on “Paul Giamatti” is a marvel of clammy self-loathing and neuroses—in that sense, it has more in common with the “Charlie Kaufman” of Charlie Kaufman’s Adaptation (played by Nicolas Cage) than with Malkovich’s ruthless parody of himself—and Giamatti’s performance plumbs depths the movie itself can’t muster. Playing a tortured New York stage actor driven to the brink by his role in Uncle Vanya, “Giamatti” seeks help from an organization that extracts human souls and keeps them in storage. (His has the color and dimension of a chickpea.) When he goes back to rehearsal, freed from the albatross of having a soul, Giamatti breezes through his lines with confidence and zeal, which isn’t right for Chekhov, either. Thus, Giamatti’s achievement in Cold Souls is to play two different kinds of bad actors well: One who’s so wrapped up in Method torture that he can barely perform, and another who’s fundamentally incapable of giving the work the gravitas it needs.


[pagebreak]12. William Shatner, Free Enterprise
Of all the actors on this list, it’s most tempting to think of William Shatner in Free Enterprise as playing himself, and not just a parody, spoof, or comic character. And yet of all the actors on this list, he may well be the most insistent in proclaiming that “Bill” in the film is not in any way related to the real Bill Shatner, even though the character is a paunchy, somewhat defeated, perennially hammy ex-Star Trek star who hails from Canada. When a couple of would-be filmmakers (and science-fiction fan-dorks) meet him in a book store, they fall over themselves to praise him; he gently tries to escape, with the air of a man used to dealing with crazy Trek fans, but they lure him in with the promise of a film project in the making. He’s just hungry and desperate enough to follow them around, hoping for their cinematic crumbs, though his real goal in life is to produce a rap musical version of Julius Caesar in which he plays all the parts. Given Shatner’s famous love of earache-inducing musical performances, that does actually sound like something he’d get involved in.

13. Bruce Campbell, My Name Is Bruce
Bruce Campbell’s latest directorial project, My Name Is Bruce, pushes the limits of self-satire almost to their breaking point. He stars as himself in a film about Bruce Campbell, a failing B-movie star who lives in a trailer, nurses himself to sleep every night with whiskey, and starts fights with obsessive fans. One of those fans, who accidentally looses an ancient spirit on a small town, kidnaps Campbell in the hopes that he’ll rally to the rescue. It’d seem like a Bruce Campbell fantasy—saving the day in real life, like he does in the Evil Dead films—if not for his depiction of himself as a womanizing lout. But Campbell, always adept at winning onscreen personas, manages to redeem even this insistently self-deprecating character with a smile. And, of course, a chainsaw.

14. Mystery guest, Zombieland
A redneck zombie-hunting badass played by Woody Harrelson makes a special point of looking up his favorite movie star during a jaunt to zombie-plagued southern California in the winning action-comedy Zombieland. The mere possibility of an appearance by the aforementioned mystery guest star invites giddy anticipation; his actual guest turn is liable to cause mass pandemonium/exhilaration, at least for filmgoers who haven’t yet discovered his identity from spoiler-happy reviews and websites. Self-deprecating hilarity ensues, as Guest Star X looks wryly back on his life and career through the prism of a most inconvenient zombie holocaust.


15. Jon Favreau on The Sopranos
Writer-director-actor Jon Favreau doesn’t have the kind of outsized public persona that would make him a natural candidate for self-parody. So for his memorable guest appearance in the Sopranos second-season episode “D-Girl,” he submits himself as an archetypical movie-star schmuck trying to buddy up to real-life bad guys in the name of research—including Christopher Moltisanti (played by Michael Imperioli), who discusses his mafia screenplay with Favreau, and inadvertently ends up contributing an anecdote about a made guy getting a blowjob from a man, which Favreau incorporates into his own mob-related script. The kicker is that at the same time, the real-life Favreau was writing and directing a poorly received crime film, Made. That film even includes three Sopranos cast members—Drea de Matteo, Vincent Pastore, and Federico Castelluccio.

16. Bruce Willis, What Just Happened
In Art Linson’s clever, appealingly modest show-biz memoir What Just Happened? Alec Baldwin belligerently refuses to shave off his beard for The Edge, one of many films Linson produced. In the poorly received film adaptation of Linson’s book, Bruce Willis happily steps into the Baldwin role to play a toxic, obnoxious version of himself, a macho action star who throws a violent temper tantrum when the film’s Linson surrogate (Robert De Niro) asks him to shave off his unflattering facial hair for a role. Willis has big fun spoofing his image as an out-of-control monster of id and ego.


17-20. Bob Saget, Jeffrey Tambor, Matt Damon, and Gary Busey, Entourage
At its best, Entourage highlights Hollywood’s dickish weirdness simply by turning the camera on its stars. But the movie’s peek behind the curtain gets better when real-life celebrities show up and interact with Vince and the boys. Bob Saget has had a recurring role, in what’s clearly yet another shot at sullying his squeaky-clean Full House image. (We get it, Bob, you like dick jokes.) On Entourage, he takes it to the next level as a neighbor who’s interested in hookers and blow, and not afraid to talk about it. Other notable against-type cameos in recent Entourage history include Matt Damon, who shook Vince down for charity money, and Jeffrey Tambor, who apparently cheats at golf and has very little nice to say about anybody, particularly Ari. And then there’s the season-four arc in which Gary Busey does an amazing impersonation of himself as a total loon. Makes you wonder how much prep work he had to do.

21-plus. Steve Coogan, Alfred Molina, and many others, Coffee And Cigarettes
Shot in segments over the course of more than 15 years, Jim Jarmusch’s sketch collection Coffee And Cigarettes centers on celebrities playing “themselves” in awkward inter-celeb encounters: Iggy Pop eagerly sucks up to a dismissive, deliberately cruel Tom Waits, Jack White raves about Nikola Tesla, over Meg White’s indifference; a reserved Bill Murray plays waiter to RZA and GZA (“You’re Bill Murray! Bill Groundhog Day ghostbustin’-ass Murray!”) and so forth. There’s a lot of exceedingly dry humor, and a lot of discomfort caused by one partner in any given conversation pushing the other too hard, but the squirmiest of the many squirmy moments comes in a coffee date between Steve Coogan and Alfred Molina, as the latter explains that he’s an amateur genealogist who’s just figured out that the two men are cousins. Molina initially comes across as bumbling but sweet, until he edges into creepiness: “All I want, if I want anything, is for you to just acknowledge this extraordinary thing, and just love me.” Coogan, meanwhile, seems like a normal guy in an awkward situation, until he finds out that his clingy new cousin is buddies with a certain prominent director, at which point he’s suddenly far more interested in their family connection, and far less interested in his dignity. Actually, dignity and remove play a large part in Coffee And Cigarettes: Its celebrities are having fun pretending that in real life they’re obnoxious gits, but only in the most delicate, genteel, intellectual ways.

…And a whole lot more, Extras
Every episode of Ricky Gervais’ short-but-sweet single-camera comedy finds his fictional character Andy Millman or Andy’s friend Maggie Jacobs (played by Ashley Jensen) on the set of a movie, playing some tiny role. Unfortunately, this sometimes means interacting with the stars, inevitably played by celebrities willing to poke fun at themselves and the star-worship culture around them. The series had nary a weak link, but highlights included Chris Martin as a self-promoting sellout, Clive Owen as a insensitive jackass, Orlando Bloom as an insecure egomaniac, David Bowie casually turning Gervais’ emotional agonies into a catchy song, a foul-mouthed Kate Winslet counseling Maggie about sex using uncomfortable euphemisms, and more. But the award for most outrageous is shared among Star Trek: The Next Generation star Patrick Stewart and Daniel Radcliffe, a.k.a. filmdom’s Harry Potter. Andy sneaks into Stewart’s on-set trailer to promote his screenplay, and winds up awkwardly listening to Stewart brag about his own plot ideas, which are invariably cheap excuses to get girls naked. Radcliffe’s characterization covers stars’ big egos: He plays himself as a spastic virgin, desperately trying to play it cool and get laid. After he hits on Maggie on a movie set and she rejects him, he tattles to his mother, claiming “She was trying to have it off with me!” Then, while showing off the fact that he owns a condom, he accidentally winds up draping it over Diana Rigg’s head. Extras mined discomfort for laughs, and these particular stars helped the show strike gold.