The 50 Funniest Cameos in Movie History

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This week, Olive Films is releasing, for the first time on Blu-ray, The Road to Hong Kong , the last of the seven “Road” buddy comedies starring Bob Hope and Bing Crosby. Hitting theaters a full decade after the penultimate entry, Hong Kong is an occasionally funny and occasionally wheezy bit of business, with one honest-to-God great sequence: an unbilled cameo by Peter Sellers, who strolls into the picture and steals the damn thing outright. Hope and Crosby were early adopters of the kind of inside-joke comedy that yielded such cameos, which became increasingly common in the years that followed; we’ve gathered up some of the funniest in movie history.

Peter Sellers in The Road to Hong Kong

Sellers’ turn as an Indian doctor, like his feature-length performance in Blake Edwards’ The Party six years later, manages to mostly dodge the pitfalls of “brownface” thanks to the good nature of the performer in question; you never feel that Sellers is laughing at his creation, but enjoying him. The scene was, reportedly, mostly improvised, with Hope and Crosby cracking up off-camera through the shooting day — and you can see why. As Sellers biographer Roger Lewis succinctly put it, “He totally upstages them.”

Dean Martin and Jerry Lewis in The Road to Bali / Bob Hope and Bing Crosby in Scared Stiff

Hong Kong was far from the first time Hope and Crosby called upon their celebrity friends to pop in on the freewheeling, fourth-wall-breaking Road pictures. The most memorable cameo, aside from Sellers, comes in their second-to-last effort from 1952. Then up-and-coming comedy team Martin and Lewis make a quick, unexpected, and funny appearance in a dream sequence (while Hope and Crosby are each dreaming of lovely leading lady Dorothy Lamour, she’s dreaming of Martin — and Lewis). The following year, Hope and Crosby repaid the favor by popping up in Martin and Lewis’ Scared Stiff (itself a loose remake of Hope’s 1940 comedy The Ghost Breakers), in what was dubbed a “comedy trade.” And somewhere, the whole Will Ferrell-Vince Vaughn-Ben Stiller gang took notes…

Bing Crosby in The Princess and the Pirate / My Favorite Brunette

Even when Hope worked solo, audiences kept expecting his old buddy Bing to show up — and he obliged, in My Favorite Blonde, Cancel My Reservation, and Alias Jesse James, among others. But the best of Bing’s pop-ins come in Princess and Brunette (featuring co-star Lamour), and they made audiences wait for ‘em. Bing shows up in the very last moments of the former, much to Hope’s consternation (“How d’ya like that, I knock my brains out for nine reels and the bit player from Paramount comes over and gets the girl!”), and to Crosby’s in the latter (he plays an executioner who is bitterly disappointed when Death Row inmate Hope is saved at the last minute).

Bill Murray in Zombieland

As we’ve all learned by now, Bill Murray can show up just about anywhere: an engagement photo shoot, a bachelor party, a karaoke bar. But even that reputation doesn’t quite prepare you for his surprise appearance in the 2009 horror comedy Zombieland, playing his most delicious character: Bill Murray. Having disguised himself as a zombie after the undead apocalypse so he can continue living his charmed live, he’s as laid-back, funny, and Zen as we’ve come to expect.

Michael Shannon in They Came Together

When you think Michael Shannon, you think — thanks to his roles in Revolutionary Road, Take Shelter, Man of Steel, and on Boardwalk Empire — total intensity. And he beautifully turned that image on its head when he popped up in David Wain’s uproarious spoof of romantic comedies, as a character who’s a touch more unbalanced than the frothy rom-com norm.

John Hurt in Spaceballs

Sometimes, all you need to create a great comic cameo is just to get someone to show up. The one scene anyone who saw Alien — and many who didn’t — never forgot is the title character’s first appearance, via poor John Hurt’s stomach. Hurt knew it was his claim to fame, so he probably figured “Why the hell not?” when Mel Brooks offered him the chance to do this “Not again!” recreation in Spaceballs — with a twist.

Gene Hackman in Young Frankenstein

Hackman had just won the Academy Award for The French Connection when he donned a wig and full beard to make an unbilled appearance as a kindly blind priest who (briefly) befriends Peter Boyle’s monster in Mel Brooks’ uproarious Frankenstein spoof. In that brief but unforgettable scene, he reminds us that sometimes those with reputations as dramatic actors make for the funniest screen comedians; he plays the character’s earnestness totally straight, without a wink, and renders the slapstick of the sequence all the more effective.

Count Basie in Blazing Saddles

Brooks again, and the joke is simple but elegant. Black Bart (Cleavon Little), the hero of Mel Brooks’ uproarious and subversive Western parody, gets a hero shot (complete with Gucci saddlebag) as he rides off across the plains, revealing the source of his lively jazz accompaniment: the Count Basie Orchestra, going to town on a bandstand right there in the middle of nowhere.

Everyone in Silent Movie

By the time Brooks made Silent Movie in 1976, the one-two punch of Frankenstein and Saddles had made him the toast of Hollywood, able to get just about anyone he wanted for his pictures. So he took advantage of that when creating his next comedy, a recreation of a silent movie, about a filmmaker trying to recreate a silent movie. He got a host of Hollywood stars to show up and turn down his on-screen avatar — including Burt Reynolds, James Caan, Liza Minelli, Paul Newman, and his wife Anne Bancroft. But the best bit belongs to famed mime artist Marcel Marceau, who responds to the offer with the film’s only spoken word.

Everyone in The Muppet Movie

The inaugural Muppet motion picture is another film with so many great cameos, it’s hard to pick out one: James Coburn as a cowardly bar owner? Richard Pryor as a trickster balloon salesman? Elliot Gould hosting a county fair beauty pageant? Orson Welles as exactly the kind of studio bigwig he could never get past himself? But our favorite is probably Steve Martin’s “Insolent Waiter” (that’s how he’s billed!), serving Kermit and Piggy at his sneering best, and popping the cap on a bottle of “Sparkling Muscatel, one of the finest wines of Idaho.”

Everyone in Austin Powers in Goldmember

The sheen of the Austin Powers pictures had grown pretty dull by the time they arrived at this third go-round, but it sure starts off with a bang: a pitch-perfect, would-be blockbuster movie-within-a-movie wherein every reveal of the series’ movie star iterations gets another laugh: Tom Cruise as Powers, Gwyneth Paltrow as his leading lady, Kevin Spacey as Dr. Evil, and Danny DeVito as Mini-Me, with the whole thing directed by an Oscar-waving Steven Spielberg.

Everyone in Anchorman

It’s tough to say when the legendary news-team rumble goes from a cute idea to a great comic sequence, but I’m gonna say it’s when Tim Robbins shows up, sucking on his pipe, repping the local PBS affiliate.

Everyone in Anchorman 2

As with any sequel, the pressure was on for Anchorman 2 to not only match its predecessor, but improve upon it. Opinions vary as to whether they pulled it off (your film editor is firmly pro-A2), but most parties agree that the follow-up rumble is even better than the original — and it’s certainly busier, since there are now scores of pay-cable outlets to work into the mix. The pacing here is aces; they keep piling on more famous faces, and by the time Harrison Ford shows up and turns into a “were-hyena,” they’ve crossed over from sequel to surrealism.

Jack Benny in It’s a Mad, Mad, Mad, Mad World

It’s tempting to include Stanley Kramer’s 1963 comic extravaganza in the “everyone” category — but, as much fun as that movie is, too many of the cameos just sit on the screen and don’t go anywhere (hey, let’s just show the Three Stooges, but don’t have ‘em actually do anything). Benny’s appearance, however, is warm and wonderful and perfect, stopping the chaotically paced picture for one of his perfectly timed pauses before his “Well!” catchphrase.

Martin Sheen in Hot Shots! Part Deux

Here’s a movie getting so meta, you wonder if it’s going to implode. In the very funny Rambo spoof Hot Shots! Part Deux, Charlie Sheen goes on a journey upriver, and we realize the film is sending up a new target: Apocalypse Now, starring Charlie’s dad, Martin. And just as that realization sets in, here comes Sheen, seemingly still on the boat from that movie. And as their vessels pass, the father and son shout at each other, “I loved you in Wall Street!” — the Oliver Stone movie in which they co-starred as father and son. Boom.

Charlie Sheen in Being John Malkovich

When Malkovich blew everyone’s mind back in ’99, the idea of Charlie Sheen as John Malkovich’s level-headed confidante was already funny — and that was before the whole “winning”/“tiger blood” nonsense. So here we have a rare celebrity cameo that’s even funnier now than when it first appeared.

Tony Curtis in Paris When It Sizzles

Richard Quine’s 1964 comedy allows its cameos, as many others have, by taking on the most celebrity-heavy city in the world: Hollywood. Thus we have Curtis’ very funny turn, briefly romancing star Audrey Hepburn in the guise of “one of those mumbling, scratching actors, destined only for minor roles and character parts.” But Hepburn’s character at least gets to pick who he looks like.

Bruce Willis and Julia Roberts in The Player and Ocean’s 12

One of the best of all Hollywood satires is Robert Altman’s The Player, and while its parade of stars gleefully shit-talking their industry is a delight, Altman holds his best joke until the end. Throughout the movie, every proposed motion picture is pitched with Bruce Willis or Julia Roberts in the lead, as was the custom in the early ‘90s, except for one: the tough, downbeat Habeas Corpus, which is to star unknowns and buck conventions with its unhappy ending. But when we arrive at the end of the story, Habeas Corpus now features, wouldn’t ya know it, Bruce Willis saving Julia Roberts’ life and walking off with her into a happy ending. The duo reunited 12 years later in Ocean’s 12, with Willis crashing the picture’s risky but remarkable third-act meta-narrative of Tess (Roberts) pretending to be Julia Roberts, and bumping into Willis, who shares celebrity war stories with her (on Sixth Sense Monday-morning quarterbacks: “If everybody’s so freaking smart, how come the movie did $675 million worldwide?”).

Oprah Winfrey in Ocean’s 13

Maybe it’s not even Oprah showing up that’s so funny. Maybe it’s that perfectly timed, perfectly composed cutaway of Clooney, Pitt, and Damon watching her show.

Chuck Norris, Dodgeball

Dodgeball isn’t exactly an innovative comedy (though it is a funny one), but this 2004 movie was ahead of the curve in one key aspect: it predated, by at least a year, the Internet meme of “Chuck Norris facts.” Dodgeball knew what Conan O’Brien knew — that the funniest thing about Chuck Norris may just be the fact that he exists.

Bob Saget in Half Baked

“Marijuana is not a drug! I used to suck dick for coke!” announced Saget, then best known for his squeaky-clean appearances on Full House and America’s Funniest Home Videos. “Now that’s an addiction, man! You ever suck some dick for marijuana?”

Merv Griffin in The Man With Two Brains

Sure, celebs are good sports; they’ll play against type or send up their own image in a movie cameo. But hats off to Merv Griffin for going along with the joke, in Carl Reiner’s 1983 Steve Martin vehicle, that (spoiler alert for a 30-plus-year-old movie) the affable talk show host lives a double life as “the Elevator Killer.” “I don’t know,” he confesses. “I’ve always just loved to kill. I really enjoyed it.”

Elliott Gould and Julie Christie in Nashville

There are so many characters banging up against each other in Robert Altman’s 1975 masterpiece Nashville that it doesn’t even come as a surprise when Gould and Christie (refugees of earlier Altman efforts like M*A*S*H and McCabe and Mrs. Miller) wander through a get-together. They don’t even do anything particularly funny, but there’s something utterly perfect about the whispers surrounding them (“He was married to Barbra Streisand, that girl that sang ‘People’”), which predict the shoptalk of The Player.

Ben Affleck, Matt Damon, and Gus Van Sant in Jay and Silent Bob Strike Back

Much of Kevin Smith’s 2001 (initial) wrap-up to the “View Askewniverse” plays like an extended inside joke/autofellatio session, particularly viewed from the vantage point of his subsequent self-obsession. But credit where due: the sequence that finds our heroes on the set of Good Will Hunting 2: Hunting Season is pure comic gold, from the cutaways of director Van Sant literally counting his money to Affleck playing himself as a hooker-courting numbskull to the priceless meta-gag about Affleck and Damon appearing in Jay and Silent Bob itself (“You gotta do the safe picture. Then you can do the art picture. But then sometimes you gotta do the payback picture because your friend says you owe him.” And they both shoot the camera a loaded look).

Matt Damon in Eurotrip

Damon appeared in three movies in 2004. Two of them — Ocean’s 12 and The Bourne Supremecy — were starring vehicles and sequels to major tentpoles, which makes it that much odder that his third release of the year is Eurotrip, a decidedly low-rent teen sexy comedy heavily promoted for featuring Buffy’s Michelle Trachtenberg in her underwear. So, what the what? Well, funny story: Damon was in Prague shooting The Brothers Grimm at the same time as the Eurotrip team, which included writers Alec Berg and David Mandel and co-writer/director Jeff Schaffer — all of whom were buddies from Damon’s Harvard days. And that, friends, is how you get one of the world’s biggest movie stars to come sing “Scotty Doesn’t Know” for your dumb road trip movie.

Danny Glover in Maverick

When Mel Gibson reunited with (then) three-time Lethal Weapon director Richard Donner for this film adaptation of the James Garner TV series, it was probably inevitable that Glover was going to show up, if only briefly — and it was probably even more inevitable that said appearance would include a mention of getting too old for a particular type of shit.

Steve Buscemi in The Wedding Singer

Buscemi is an indie icon, a favorite of everyone from the Coen Brothers to Quentin Tarantino to… Adam Sandler. Yes, since the odd couple co-starred in Airheads, Buscemi has appeared in no fewer than 11 Sandler vehicles, usually faring no better than any of the other assortment of Sandler buddies (Schneider, Spade, Nealon, et al.) who make up that rep company from hell. But there is one exception: his memorable turn in Sandler’s not-half-bad 1998 picture The Wedding Singer, where he contributes a wildly inappropriate wedding toast.

Bob Barker in Happy Gilmore

More often than not, the cameos in Sandler movies are especially grating and unfunny, with celebrities and actors trotted out for lazy jokes (if any — sometimes they’ll just plop a random star into the middle of the screen and leave them there). The notable exception to the rule, of course, is the Price Is Right host’s memorable turn in Sandler’s 1996 comedy Happy Gilmore, which cleverly sends up Barker’s nice-guy image and lets him deliver the movie’s best rejoinder.

Johnny Depp in 21 Jump Street

It wasn’t much of a surprise when such original cast members as Holly Robinson Peete and Peter DeLuise popped up in the Phil Lord and Christopher Miller-directed 2012 film adaptation of Jump Street — I mean, c’mon, they were probably free. But the film’s marketing materials did a bang-up job of keeping the appearance of breakout series star Johnny Depp a secret, and there wasn’t much of a reason to think he might show up; he didn’t exactly seem nostalgic for the show, and spent several years after his impatient exit shaking off the heartthrob image he’d acquired there. So his cameo in the film is perfectly executed: late in the movie (by which time you’ve kinda forgotten about him), cleverly concealed behind layers of makeup, and then quickly, unexpectedly disposed of. And here’s a nice bit of background: Depp’s single condition for the cameo was that it would pair him with DeLuise, his best buddy during the show’s run.

Peter Jackson and Cate Blanchett in Hot Fuzz

The smashing success of Shaun of the Dead allowed creators Edgar Wright and Simon Pegg to call upon an impressive array of talent for supporting and cameo roles in their follow-up, Hot Fuzz. But the picture’s two best surprises are its sneakiest. First, Peter Jackson makes a blink-and-you’ll-miss-it appearance (seriously, it’s like a second a half) as a Santa-suited criminal stabbing Pegg in the hand. And then there’s his LOTR star, Blanchett, whose single scene is played entirely behind a face-obscuring crime-scene mask.

Michael Keaton and Samuel L. Jackson in Out of Sight

When Out of Sight arrived in theaters in summer of 1998, it wasn’t just carrying the weight of a comeback for director Steven Soderbergh. It was also burdened with the inevitability of comparisons to Jackie Brown, Quentin Tarantino’s highly acclaimed (and long-awaited) follow-up to Pulp Fiction — and another adaptation of a book by Out of Sight author Elmore Leonard. But instead of running from those comparisons, Soderbergh seemed to invite them. First, he had Brown’s Keaton reprise his character of agent Ray Nicolet for a brief, unbilled appearance in Out of Sight, connecting the two films within the Leonard universe. And then, he pulled in Tarantino’s favorite actor, Samuel L. Jackson, for a surprise appearance in Sight’s final scene, crafting a delightful coda (not found in the book) that took full advantage of Jackson’s badass baggage.

Will Ferrell in Wedding Crashers

By the time Wedding Crashers was released in the summer of 2005, the so-called “Frat Pack” had done enough films in various combinations (Anchorman, Starsky & Hutch, Old School, etc.) that the absence of Ferrell seemed almost conspicuous. So his late, unbilled appearance prompted cheers among the picture’s target audience — and some of the movie’s biggest laughs (“Mom! The meatloaf! Fuck!”).

Joan Rivers in The Muppets Take Manhattan

Also known as the moment every kid in America discovered Joan Rivers.

Alice Cooper in Wayne’s World

It’s the easiest trick in the book: the celebrity cameo that plays against expectations by, say, presenting a nutty rock star as a quietly intellectual American history buff. But hey, if it works, it works.

Charlton Heston in Wayne’s World 2

Wayne’s World’s 1993 sequel was a considerably spottier affair, but it did give us one wonderfully nutty meta-moment: when Mike Myers’ Wayne complains about the poor acting of a day player and asks if they can get a better actor (“I know it’s a small part, but I think we can do better than this”). Turns out, they can!

Dustin Diamond in Made

When your single claim to fame is playing the geek on a bad teen show, your subsequent public life can be a tough row to hoe — as we’ve seen from poor Dustin “Screech” Diamond’s various adventures in knife-wielding and sex-taping. In fact, Diamond’s done best when he’s leaned in to his dubious celebrity, as he did in this marvelously self-deprecating and slyly cool cameo in Jon Favreau’s 2001 comedy Made.

Salman Rushdie in Bridget Jones’s Diary

Included at the insistence of Flavorwire Editorial Assistant Alison Herman, because (in her words) “lol, what.”

Kareem Abdul-Jabbar in Airplane!

“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!”

Brett Favre in There’s Something About Mary

Favre’s not quite as adept with his line readings as Abdul-Jabbar, but this is still a pretty great entry in the limited realm of athlete cameos in movie comedies — particularly for the scene after, with Stiller’s hilarious mispronunciation of “Brett Fav…ruh.”

Hulk Hogan in Gremlins 2: The New Batch

Yes, this is how big pro wrestling was in 1990. It was a strange time.

Xavier McDaniel and Tim Burton in Singles

But the best athlete cameo in a movie ever is (apologies to Kareem) Xavier McDaniel’s pop-up in Cameron Crowe’s Singles, giving an uproarious twist to the old saw about how to… delay gratification. And McDaniel isn’t the only spot-on cameo in Singles: Tim Burton makes an unexpected appearance as the moody auteur of a video dating service, a man referred to as “the next Martin Scor-seeze.” (And if you’ll follow me down the rabbit hole for a moment, that same mispronunciation is heard in Birdman, a film with no small connection to star Michel Keaton’s Batman films… directed by Tim Burton.)

George Harrison and Spike Milligan in The Life of Brian

When funding for Monty Python’s biblical epic was pulled at the 11th hour, Harrison stepped up with the money to make the film, for no other reason than that he wanted to see it. (Eric Idle later called his investment “the world’s most expensive cinema ticket.”) And that explains Harrison’s brief, silent, unheralded cameo in the film, a nice giggle for those in the know. (A year earlier, Harrison also made a very funny, and very disguised, appearance in Idle’s Beatles spoof documentary The Rutles: All You Need is Cash.) Also popping up in Life of Brian was one of the Pythons’ idols, Spike Milligan, who just happened to be visiting Tunisia during the shoot; he was hastily added in to that day’s shooting and promptly disappeared once his scene was shot.

Bruce Springsteen in High Fidelity

Cameos by musicians can range from awesome to painful, but The Boss’ surprise appearance in Stephen Frears’ adaptation of Nick Hornby’s novel is downright delightful — and makes complete sense, since Bruce is exactly the kind of guardian angel our hero Rob would conjure up.

David Bowie in Zoolander

“I believe… I might be of service.”

Rihanna in This is The End

Seth Rogen and Evan Goldberg’s Hollywood apocalypse comedy has plenty of self-referential appearances, but Rihanna’s is probably the funniest — and the most satisfying, what with that whole slapping-the-shit-outta-Michael-Cera thing.

Dave Grohl in The Muppets

Look, the entire concept of “The Moopets” — a Muppet cover band, fronted by single original member Fozzie — is one of the funniest things in James Bobin’s 2011 Muppet reboot, as anyone with even a passing familiarity with rock revival tours can tell you. (It’s Herman’s Hermits, featuring the original drummer and three other people who weren’t in the band!) But throw in Grohl — the only human member, by the way — in full-on Animal get-up and you’re talking comedy gold.

DMX in Top Five

Chris Rock’s semi-autobiographical comedy is full of great cameos by his celebrity friends (Seinfeld’s credit cookie rundown of his top five rappers is a highlight), but the best bit in the movie is, again, the one you’re least expecting: when Rock’s Andre lands in jail and finds himself being serenaded by DMX, whose rendition of Charlie Chaplin’s ballad “Smile” is, if nothing else, heartfelt.

Eminem, Ray Romano, and James Taylor in Funny People

Like Top Five, Judd Apatow’s slightly fictionalized riff on the life of a comedy superstar (in this case, his friend and star Adam Sandler) is stuffed with comics playing themselves. But the two funniest cameos come from musicians: Eminem, complaining about fame and starting up beef with Ray Romano, and James Taylor, who delivers the punchline of the movie’s MySpace scene like a champ.

Kurt Vonnegut in Back to School

“And another thing, Vonnegut: I’m gonna stop payment on the check!… Fuck me? Hey, Kurt, can you read lips? Fuck you! Next time I’ll call Robert Ludlum!”

Marshall McLuhan in Annie Hall

This isn’t a ranking, but I did save my all-time favorite celebrity cameo for last — if, for no other reason, than the fact that it concludes with the unstated theme of pretty much every celebrity movie cameo: “Boy, if life were only like this!”