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  4. 18 times celebrities played fictionalized versions of themselves

18 times celebrities played fictionalized versions of themselves

18 times celebrities played fictionalized versions of themselves
Matt Damon and Ben Affleck in "Jay and Silent Bob Strike Back."Miramax Films
  • These stars don't take themselves too seriously.
  • They proved they're in on the joke by appearing in movies as themselves.

Debra Messing has a laugh-out-loud cameo as a version of herself who is exhausted from hearing about gay men's problems in 2022's "Bros."

Debra Messing has a laugh-out-loud cameo as a version of herself who is exhausted from hearing about gay men
Messing in "Bros."      Universal Pictures

"Bros" is mainly a romantic comedy about Bobby (played by Billy Eichner) working through his commitment issues to be with Aaron (played by Luke Macfarlane), who has his own baggage.

But a side plot involves Bobby's job as the curator of New York City's new National LGBTQ+ History Museum, and his attempts to get the museum up and running. At one point, he's slotted to give noted gay icon and "Will & Grace" star Messing a tour of the new museum.

Instead, he opens up to her about his relationship woes, causing Messing to (hilariously) break down, screaming that she is not her character from "Will & Grace," and that she's sick of gay men unloading all their problems on her, before declaring that lesbians are much more put together.

Messing told People magazine in September 2022 that Eichner, who also cowrote the movie, had reached out to her about appearing in it.

"I was shocked and just so grateful that he reached out and was like, 'We can't do this without you. You have to be in this,'" she said, adding: "I play Debra Messing. A very heightened version, which was very, very fun to do."

Colin Firth plays an employee at a burrito stall called Love Guac'tually, named Colin, in "Rye Lane."

Colin Firth plays an employee at a burrito stall called Love Guac
Firth in "Rye Lane."      Searchlight Pictures

Sure, this may not technically be the real Firth, but the characters in the 2023 rom-com "Rye Lane" make it a point to call him Colin, and the name of his place of employment, Love Guac'tually, is a clear nod to Firth's holiday classic "Love Actually."

Also, in the film, one of the main characters Dom (played by David Jonsson), is reeling from a breakup with his girlfriend, whom he discovered was cheating him with his best friend. That makes him eerily similar to Firth's characters in "Love Actually," where his girlfriend was cheating on him with his brother, and "Bridget Jones' Diary," where his fiancée cheated on him with his best friend.

Shaun White plays an aggressive, foul-mouthed version of himself in 2011's "Friends with Benefits."

Shaun White plays an aggressive, foul-mouthed version of himself in 2011
White in "Friends with Benefits."      Sony Pictures Releasing

A still-long-haired White pops in for two scenes of the rom-com "Friends with Benefits," which stars Mila Kunis and Justin Timberlake as Jamie and Dylan, respectively, two best friends who decide to try sleeping together with no strings attached.

In both cases, Timberlake's Dylan makes the worst possible impression on White, who seems to be holding a torch for Jamie and is ready to throw hands at a moment's notice.

Neil Patrick Harris revitalized his career with his turn as a drug-using, womanizing, party boy version of himself in "Harold & Kumar Go to White Castle" and its two sequels.

Neil Patrick Harris revitalized his career with his turn as a drug-using, womanizing, party boy version of himself in "Harold & Kumar Go to White Castle" and its two sequels.
Harris in "Harold & Kumar Go to White Castle."      New Line Cinema

Harris steals the show in 2004's "Harold & Kumar Go to White Castle" when he makes his first appearance, high on ecstasy and begging Harold and Kumar for a ride. He goes on to steal their car. In real life, Harris is a happily married man with two children, and no ecstasy habit to speak of.

The first installment of the "Harold & Kumar" saga was released two years before Harris came out as gay — but the third installment, 2008's "A Very Harold & Kumar 3D Christmas," addresses this by claiming that Harris and his husband, David Burtka (who also appears as himself), are faking their relationship, and that Harris is pretending to be gay to take advantage of women.

Harris' role in the movie, which is about two stoners who desperately want to get to White Castle to grab some munchies, was instrumental to his current success. Before "Harold & Kumar," he was only known for his role as Dr. Doogie Howser in "Doogie Howser, MD," when he was just a teen. The roles just weren't coming in, according to Harris, The New York Times reported.

So, without "Harold & Kumar," we probably wouldn't have Barney Stinson, his iconic opening number at the Tony Awards, or the newest iteration of "A Series of Unfortunate Events."

Both Selena Gomez and Margot Robbie appear in "The Big Short" as themselves. They're both used to explain complicated financial terms to the audience in ways the average viewer could understand.

Both Selena Gomez and Margot Robbie appear in "The Big Short" as themselves. They
Gomez and Robbie in "The Big Short."      Paramount Pictures

"The Big Short," which details the events leading up to 2008's financial crisis, introduces the typical moviegoer to many complex financial terms and situations, which is where Robbie, Gomez, and a few other celebrities come in.

Gomez appears at a blackjack table next to Nobel Prize-winning economist Richard Thaler. She's tasked with explaining what a synthetic CDO is, by using the simple metaphor of a blackjack game.

Robbie's scene is her in a bubble bath drinking Champagne, and explaining what exactly the mortgage crisis was — that banks were issuing riskier and riskier mortgages in order to keep profits up.

Everyone in "This Is the End" played fictionalized versions of themselves, but Michael Cera's cocaine-fueled monster was the highlight.

Everyone in "This Is the End" played fictionalized versions of themselves, but Michael Cera
Cera in "This Is the End."      Columbia Pictures

To be fair, everyone plays a pretty terrible version of themselves in "This Is the End," which depicts what would happen to a bunch of Hollywood stars during the apocalypse, but Cera's performance as an angry coke-head who screams at all his friends is pretty hilarious.

It goes directly against the nerdy persona he established in "Scott Pilgrim vs The World" and "Superbad." No one wants to think that the sweet Paulie Bleeker from "Juno" is actually a mean-spirited maniac.

Fittingly, Cera goes out on an embarrassing note. He accuses all of his friends of stealing his cell phone, gets impaled by a fallen street light, and then realizes he had his phone the whole time. He then meets his demise by descending into a fiery sinkhole.

John Malkovich loaned his face and name to surrealist comedy "Being John Malkovich."

John Malkovich loaned his face and name to surrealist comedy "Being John Malkovich."
Malkovich in "Being John Malkovich."      USA Films

The plot of "Being John Malkovich" is just bizarre — an employee of a shady company finds a tunnel that leads to the inside of Malkovich's mind. Anyone who crawls through the tunnel can take over Malkovich's body — so when Malkovich himself crawls through the tunnel, things get a little weird.

He enters a strange world in which every single person has his face, and the only word anybody can say is "Malkovich." In a movie full of memorable moments, this scene takes the cake.

Malkovich himself has said that he doesn't feel connected to this version of himself: According to The New York Times, he told the director to "'Turn it up.' Who better to make fun of yourself — your impotence, your vanity, your ridiculousness — and say it's okay? I am ridiculous — I mean, I am a celebrity."

David Bowie only appeared in one scene of "Zoolander," but he played an important role — he judged a "walk-off" between the two main characters.

David Bowie only appeared in one scene of "Zoolander," but he played an important role — he judged a "walk-off" between the two main characters.
Bowie in "Zoolander."      Paramount Pictures

"Zoolander" is about a model, Derek Zoolander, who has to deal with becoming a has-been (and also thwart a conspiracy that brainwashes models into killing political figures).

Zoolander and his rival, Hansel, have trouble deciding who is the better model and seem to be at an impasse — until the "Space Oddity" singer and fashion icon steps up to the plate to judge their runway walk-off.

The fact that Bowie would know how to decide which model is better, and have the time and interest to judge such a contest is laughable.

Ben Stiller, the film's star, writer, and director, called working with the rock star "a high point in my career."

Eminem was interviewed in "The Interview," and he nonchalantly came out as gay — probably in response to accusations of his homophobia.

Eminem was interviewed in "The Interview," and he nonchalantly came out as gay — probably in response to accusations of his homophobia.
Eminem in "The Interview."      Columbia Pictures

Eminem is no stranger to controversy. He frequently uses slurs and problematic language in his raps — see his 2018 album, "Kamikaze" — and has been called on it many times. But the rapper has maintained he is not homophobic.

His willingness to make fun of his public persona and come out as gay during "The Interview," an already controversial movie for its plot (two Hollywood stars are tasked with assassinating North Korean dictator Kim Jong-un), proves that the real Slim Shady isn't quite as scary as he seems.

Tom Cruise appears in a movie-within-a-movie in "Austin Powers in Goldmember." He plays himself playing Powers.

Tom Cruise appears in a movie-within-a-movie in "Austin Powers in Goldmember." He plays himself playing Powers.
Cruise in "Goldmember."      New Line Cinema

The final "Austin Powers" movie is 2005's "Goldmember" which, as usual, parodies multiple "James Bond" movies. In an extra-meta moment, "Goldmember" opens with the filming of a movie about Powers' antics, called "Austinpussy" (a play on Bond film "Octopussy").

In the film, many celebrities make an appearance as the cast of "Austinpussy,' like Danny DeVito, Gwyneth Paltrow, and John Travolta. But the titular role of Powers goes to none other than Cruise, who gamely rocks a Powers wig, and velvet bell-bottom suit.

Remember: This was years before Cruise proved his comedic chops in "Tropic Thunder." Up until this point, he had been exclusively playing heroes in prestige films and dramas, like "Top Gun," "Mission: Impossible," and "A Few Good Men." It was a true surprise to see the actor known appearing in a comedy like "Austin Powers."

Justin Bieber plays a secret agent-esque version of himself in "Zoolander 2."

Justin Bieber plays a secret agent-esque version of himself in "Zoolander 2."
Bieber in "Zoolander 2."      Paramount Pictures

The sequel to "Zoolander" is just as full as celebrity cameos as the first one. But it's "No Brainer" singer Bieber who gets to play a secret agent-esque version of himself who dodges bullets, does back flips, and takes down bad guys.

Bieber ends up dying in a blaze of glory ... but not before he takes a final selfie.

Al Pacino's turn as a girl-crazy version of himself was the high point of an otherwise disappointing "Jack and Jill."

Al Pacino
Pacino in "Jack and Jill."      Columbia Pictures

The Daily Beast called "Jack and Jill," a comedy in which Sandler plays both Jack and his twin sister Jill, "the worst film ever made."

But Pacino's performance as a love-struck version of himself was deemed the movie's high point. He falls in love with Jill and even gets a good jab in at his own expense, when he makes fun of his lone Oscar win.

Pacino is known as one of the toughest guys in Hollywood — maybe you've heard of "The Godfather" or "Serpico" — so to see him as a lovesick puppy was jarring to say the least.

Bill Murray is one of the lone survivors of the zombie apocalypse in "Zombieland."

Bill Murray is one of the lone survivors of the zombie apocalypse in "Zombieland."
Murray in "Zombieland."      Columbia Pictures

During their cross-country road trip to escape zombies, the main characters of "Zombieland" arrive at Murray's Hollywood mansion. At first, the crew believes that Murray has been infected with the virus, but Murray sets them straight — he's just pretending to be infected so he can play golf in peace, making fun of his reputation as a curmudgeon.

After a prank gone wrong, he ends up getting shot in the chest. One of the characters asks if he has any regrets, and his last words are "'Garfield,' maybe..." referencing one of his worst IRL movie flops.

Tobey Maguire appears in a movie-within-a-movie in "Tropic Thunder."

Tobey Maguire appears in a movie-within-a-movie in "Tropic Thunder."
Maguire in "Tropic Thunder."      DreamWorks Pictures

"Tropic Thunder" is about a group of actors who get stranded in Vietnam while filming a war epic. When establishing the careers of each actor, they all get a fake trailer of a movie that they "starred" in.

Robert Downey, Jr.'s character, Kirk Lazarus, stars in "Satan's Alley," a melodramatic romance between two monks, clearly making fun of "Brokeback Mountain," a romance between two male ranchers. One of the monks is Lazarus, and the other is Maguire, who really commits to the part.

The "trailer" came just a year after Maguire starred in his final "Spider-Man" movie, so it was a definite surprise when he popped up, and clearly was a reference to his infamous "emo" version of Peter Parker in "Spider-Man 3."

Ben Affleck and Matt Damon are shooting the sequel to their classic "Good Will Hunting" in "Jay and Silent Bob Strike Back."

Ben Affleck and Matt Damon are shooting the sequel to their classic "Good Will Hunting" in "Jay and Silent Bob Strike Back."
Damon and Affleck in "Jay and Silent Bob Strike Back."      Miramax Films

Damon and Affleck's relationship with Kevin Smith, the silent half of Jay and Silent Bob, goes back to before their big break with "Good Will Hunting." They appeared in "Chasing Amy," which was written and directed by Smith, just a few months prior.

In "Jay and Silent Bob Strike Back," Jay and Silent Bob wander onto the set of "Good Will Hunting 2: Hunting Season," while they are trying to regain the rights to their comic book, "Bluntman and Chronic," which is being adapted into a movie by Miramax (the studio that produced the real "Good Will Hunting"). They come across Affleck and Damon, who play money-hungry versions of themselves willing to sell out for a big paycheck ... which is how they end up making "Hunting Season."

Bob Barker plays an overly competitive version of himself in "Happy Gilmore."

Bob Barker plays an overly competitive version of himself in "Happy Gilmore."
Barker in "Happy Gilmore."      Universal Pictures

In "Happy Gilmore," the titular character played by Adam Sandler is a hopeful hockey player who discovers he has a talent for golf. When he qualifies for a professional-amateur tournament, he's partnered with "The Price Is Right" host and TV institution Bob Barker.

When Gilmore starts choking and losing the game, Barker gets increasingly angry, and eventually the two end up in a physical altercation — which Barker easily wins.

Seeing Barker — someone who has comforted every kid who had to stay home sick and watch daytime TV all day — play this aggressive version of himself resulted in gut-busting laughter.

William Shatner makes two "Star Trek" fans' dreams come true in "Free Enterprise."

William Shatner makes two "Star Trek" fans
Shatner in "Free Enterprise."      Anchor Bay Entertainment

"Free Enterprise" is a 1999 rom-com about two self-proclaimed geeks who are each experiencing mid-life crises ... until they come across "Star Trek" legend Shatner in a bookstore.

Shatner plays an exaggerated version of himself — the real Shatner is a ham, but not to this extent — that wants to write, direct, and star in a one-man musical version of the Shakespeare play "Julius Caesar." He even raps!

Ryan Seacrest pokes fun at his TV persona by dropping a lot of f-bombs in "Knocked Up."

Ryan Seacrest pokes fun at his TV persona by dropping a lot of f-bombs in "Knocked Up."
Seacrest in "Knocked Up."      Universal Pictures

In "Knocked Up," a movie about a one night stand between a career-driven woman and a slacker, Katherine Heigl's character Alison works at E!, where she routinely interacts with Ryan Seacrest, who's known for his positive demeanor.

Except that in the film he's not that chipper. He complains about the softball interview questions he has to ask, drops f-bombs left and right, and claims to be more famous than the celebrities he interviews.


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