1. Brad Pitt, Jackass
Back in Feb. 2002, Brad Pitt appeared in two amazing episodes of the MTV series Jackass. In the first, he ran through the streets of L.A. causing mayhem with the other cast members in monkey suits, and in the other, he staged his own abduction.
Best Line: "Hi. I'm Brad Pitt and I'm gonna get abducted."
2. Neil Patrick Harris, Harold and Kumar Go To White Castle
In Harold and Kumar Go To White Castle—and the subsequent films in the franchise—Neil Patrick Harris plays a bats--t insane version of himself who downs mushrooms, sleeps with hookers, and is pretending to be gay as a clever ruse to get more “poon,” as he calls it.
Best Line: “Yeah, I’ve been craving burgers, too. FURBURGERS. Come on, dudes, let’s pick up some trim at a strip club. The Doogie line always works on strippers. Laaaapdaaaance!”
3. Bill Murray, Zombieland
While he’s also great in Spacejam, Bill Murray’s cameo (as himself) in Zombieland is one of the greatest examples of self-parody ever. In the film, a group of refugees during a zombie apocalypse stumble upon the home of Bill Murray, and run into what appears to be a zombie Murray. But looks can be deceiving…
Best Line: [On whether he has any regrets] “Garfield, maybe.”
4. John Malkovich, Being John Malkovich
In Spike Jonze’s brilliant 1999 surrealist film, lowly puppeteer Craig Schwartz (John Cusack) discovers a portal that leads directly into the head of actor John Malkovich. Things get dicey when Schwartz and his co-conspirators take turns controlling Malkovich’s mind.
Best Line: [During Sex] “Did you call me Lotte?”
5. Kareem Abdul-Jabbar, Airplane
In this 1980 comedy classic by Jim Abrahams, David Zucker and Jerry Zucker, a plane full of people has been poisoned by bad fish, including the co-pilots, one of whom is Roger Murdock (Kareem Abdul-Jabbar), who is in extreme denial of being the basketball legend Kareem Abdul-Jabbar, despite the fact that he gets testy when people mention his subpar defense, and wears basketball shorts while flying.
Best Line: “The hell I don’t! LISTEN, KID! I’ve been hearing that crap ever since I was at UCLA. I’m out there busting my buns every night. Tell your old man to drag Walton and Lanier up and down the court for 48 minutes.”
6. Carl Weathers, Arrested Development
In the TV series Arrested Development, Carl Weathers—of Rocky and Predator fame—portrays the acting coach of former therapist-cum-struggling actor, Tobias (David Cross). However, he seems to be more fascinated by free food and drink than, well, just about anything else.
Best Line: “Whoa, whoa, whoa. There’s still plenty of meat on that bone. Now you take this home, throw it in a pot, add some broth, a potato… Baby, you’ve got a stew going.”
7. Ben Affleck, Matt Damon & Gus Van Sant, Jay and Silent Bob Strike Back
In filmmaker Kevin Smith’s 2001 comedy Jay and Silent Bob Strike Back, Jay (Jason Mewes) and Silent Bob (Smith) travel to Hollywood to stop a movie from being made about the comic book characters based on them, Bluntman & Chronic. While wandering through the studio backlots, they find themselves on the set of the sequel, Good Will Hunting 2: Hunting Season, starring Ben Affleck and Matt Damon as crazy asshole versions of themselves. Meanwhile, director Gus Van Sant is too busy counting money in the director’s chair to give them any sort of guidance.
Best Line: “No, bulls--t, because I wasn’t WITH a hooker today, ha-HA!”
8. Wayne Brady, Chappelle’s Show
On Comedy Central’s short-lived sketch comedy series Chappelle’s Show, Dave Chappelle gets in a contract dispute with the network and Wayne Brady must step in to host the remaining episodes. When Dave comes back, he confronts Brady and then recalls a terrible night they shared when Brady, contrary to his squeaky-clean public image, terrorized him—and everyone around him—during a Training Day-esque spree.
Best Line: “Is Wayne Brady gonna have to choke a bitch?”
9. Michael J. Fox, Curb Your Enthusiasm
During the eighth season finale of HBO’s Curb Your Enthusiasm, which aired on Sept. 11, 2011, Larry David is back in New York City and when Michael J. Fox sees Larry drawing a Hitler mustache on a man in a magazine, who turns out to be his stepfather, a series of “coincidences” seem to occur—Fox gives Larry a shaken-up soda, he begins stomping around his apartment at night in boots (he lives above Larry), etc. And Larry, as is his wont, begins to think Fox is using his Parkinson’s as an excuse to harass him.
Best Line: “Let me get that. I’ll be back in two shakes.”
10. Daniel Radcliffe, Extras
Ricky Gervais and Stephen Merchant’s TV series Extras featured a number of celebrities playing outlandish versions of themselves, but the best of the bunch was Harry Potter’s Daniel Radcliffe as a ridiculously horny version of himself who goes around the set of a film, clad in a boy scout uniform, sexually harassing every woman on set—and often brandishing his condom. In one terribly funny scene, he accidentally flings his condom on the head of Dame Diana Rigg.
Best Line: “I’ve done it with a girl… intercourse wise.”
11. Liam Neeson, Life’s Too Short
The mockumentary TV series Life’s Too Short, created by Ricky Gervais, Stephen Merchant, and Warwick Davis, captures what it’s like to be Warwick Davis, an outrageous “showbiz dwarf.” In the series’ greatest scene, the gang meets with Liam Neeson—as himself—who tells them he wants to get into improv comedy. To say that he lacks the necessary chops would be a massive understatement.
Best Line: “I’ve contracted AIDS… from an African prostitute.”
12. Mick Jagger & Keith Richards, The Simpsons
On the second episode of The Simpsons’ fourteenth season, titled “How I Spent My Summer Vacation,” Marge feels guilty for not letting Homer pursue his dream of rock stardom, so she enrolls him in a Rock ‘n Roll Fantasy Camp run by the Rolling Stones’ Mick Jagger and Keith Richards (voiced by the real fellas).
Best Line: “Welcome to Rock ‘n Roll Fantasy Camp, where you’ll experience the complete rock ‘n’ roll lifestyle—without the lawsuits and STDs.”
13. Alice Cooper, Wayne’s World
Wayne (Mike Myers) and Garth (Dana Carvey) host a TV show for local cable, and Wayne is head over heels for Cassandra (Tia Carrere), a bass player/singer in an up-and-coming rock band. But the scheming Benjamin (Rob Lowe) also has the hots for Cassandra, and gives the duo backstage passes to see Alice Cooper in concert in Milwaukee. When they meet Alice, he isn’t exactly what they were expecting.
Best Line: “Actually, it’s pronounced mill-e-wah-que, which is Algonquin for ‘the good land.’”
14. Bob Barker, Happy Gilmore
In this 1996 comedy, former hockey hopeful-cum-golfer Happy Gilmore (Adam Sandler) is paired with Bob Barker in a celebrity tournament. When Happy his taunted, his game suffers, and Barker is none too pleased, leading to a brawl for the ages.
Best Line: “I don’t want a ‘piece’ of you, I want THE WHOLE THING!”
15. Mike Tyson, The Hangover
In 2009’s The Hangover, The Wolf Pack—Stu (Ed Helms), Alan (Zach Galifianakis), and Phil (Bradley Cooper)—wake up one morning after a crazy night in Vegas with no memory of the previous evening, and a tiger in the bathroom of their hotel suite. Little do they know that the owner is none other than Mike Tyson, and he will have his vengeance.
Best Line: “Like you said, we all do dumb s--t when we’re f--ked up.”
16. Seth Green, Entourage
On the HBO series Entourage, Seth Green plays a highly exaggerated, douchebag version of himself who relentlessly taunts Eric (Kevin Connolly), the diminutive manager of rising acting star Vincent Chase (Adrian Grenier), over his relationship with the gorgeous Sloan (Emmanuelle Chriqui).
Best Line: “Hey, did you tell Sloan I said what up?”
17. Patrick Stewart, Extras
Andy Millman (Ricky Gervais) is a lowly “extra”—background player—on films and TV shows in this acclaimed series, which aired on the BBC and HBO. When Millman tries to pitch a script of his show to Patrick Stewart, the actor instead returns the favor, opening up about his own project where he can undress women with his mind (a cheeky nod to his Professor X character in the X-Men films).
Best Line: “For instance, I’m walking along, and I see this beautiful girl, and I think I’d like to see her naked, and so all her clothes fall off…”
18. Billy Zane, Zoolander
In this 2001 parody of the male modeling world, when the world’s greatest male model, Derek Zoolander (Ben Stiller), crosses paths with his runway nemesis, Hansel (Owen Wilson), they decide to settle it in a “walk off.” Billy Zane, playing himself, is the man in Derek’s corner who tries to keep his ego in check.
Best Line: “It’s a walk off! It’s a walk off…”
19. Steve Coogan, The Trip
Michael Winterbottom’s 2011 film, edited down from a BBC sitcom, stars comedian-pals Steve Coogan and Rob Brydon as fictionalized versions of themselves as they go on a restaurant tour in the British countryside. The duo often engages in silly games of comedy one-upmanship, resulting in some truly hilarious impersonations.
Best Line: [in Michael Caine voice] “She was only 16 years old. She was only… You were only supposed to blow the bloody doors off!”
20. Dan Marino, Ace Ventura: Pet Detective
Miami Dolphins QB Dan Marino is kidnapped by Lt. Lois Einhorn (Sean Young), who is actually Ray Finkle—a field goal kicker who holds a years-long grudge against the QB—and it’s up to Ace Ventura (Jim Carrey) to free him. Marino has a great comedy rapport with Carrey, does a hilarious mock commercial for Isotoner gloves, and is even forced to make out with his tranny kidnapper.
Best Line: “Hey Ace… You got any more of that gum?”
21. Arnold Schwarzenegger, Last Action Hero
The premise of 1993’s Last Action Hero is that it’s a film-within-a-film, in which a young action movie buff enters the fictional movie world and pals around with Jack Slater (Schwarzenegger). It’s basically one giant parody of Schwarzenegger’s action movie persona, as well as action movies themselves.
Best Line: [As Hamlet] “To be, or not to be… Not to be.”