11. Always Be My Maybe (2019)
Who wouldn’t be starstruck ifKeanu Reeveswalked in the room? We certainly would be! And for Sasha (Ali Wong) inAlways Be My Maybe, Keanu Reeves ends up being her dinner date.
Always Be My Maybeis a very 21st century rom-com that’s subtly layered with social commentary. It follows a rich celebrity chef who rekindles her childhood friendship with failing musician Marcus (Randall Park).
After bumping into each other sixteen years later, Marcus lands in unfamiliarly wealthy surroundings for an awkward double date—and then Sasha’s new man struts in, slow-mo style, turning heads and putting the restaurant (and us) in awe.
10. Jay and Silent Bob Strike Back (2001)
Ben AffleckandMatt Damonwrote their way to fame with the screenplay forGood Will Hunting,the acclaimed film in which they starred and ended up bagging Oscars for.
In Kevin Smith’s iconic stoner comedyJay and Silent Bob Strike Back, we witness both Affleck and Damon shooting a scene for a fictional sequel:Good Will Hunting 2: Hunting Season. How very meta.
The eponymous characters in this fifth View Askewniverse movie are chased through the Miramax lot, only to arrive in front of Damon and Affleck as they’re adding spice to the famous drama film with a rifle.
Related:The Best Cinematic Universes, Ranked (And Their Best Movies)
9. The Big Short (2015)
Margot Robbie, Selena Gomez, Anthony Bourdain, and Richard Thaler all make cameo appearances to explain the nitty-gritty plot details ofThe Big Shortin a way that keeps audiences engaged.
And what better way to engage viewers on dry technical jargon than withMargot Robbiein a bubble bath?
Adam McKay’s witty crime biography looks into the 2008 financial crisis, detailing everything from hedge funds to subprime loans, from CDOs to premiums, etc.
A lot of celebrity faces and energetic montages were needed to keep it fun, but the most memorable celebrity insert involves Margot Robbie sipping champagne while explaining what mortgage bonds are. Only she could make it all sound so interesting!
Related:What Is Breaking the Fourth Wall? Great Examples in Film and TV
8. Zoolander (2001)
David Bowieis technically more of a musical legend than an actor, but he has appeared in a handful of films, including 1976’sThe Man Who Fell to Earth, 1986’sLabyrinth, and 2006’sThe Prestige.
But one of his other rare cinematic performances was as himself in the 2001 comedy filmZoolander, starring and directed by Ben Stiller. The firstZoolanderhad us in stitches, and at one point Bowie himself steps on-screen as “Let’s Dance” ripples through the speakers.
Not only is David Bowie remembered for his influence on the glam rock genre, he also made a huge impact on the fashion industry with his androgynous outfits. Thus, he was the perfect person to judge a fashion competition between Zoolander and Hansel on the runway!
Related:The Dumbest Movie Characters Who Are Still Lovable
7. Zombieland (2009)
One could argue that Bill Murray always plays a variation of himself in every movie, complete with his specific Bill Murray sense of humor. But in Ruben Fleischer’s apocalyptic comedyZombieland,Bill Murrayliterally appears as himself.
When the survivors of a zombie outbreak find themselves in the Murray mansion, they believe the actor has also been victim to the plague—but it actually turns out that he just wears zombie makeup to blend in and play golf from time to time.
When Murray’s scare-prank on Colombus backfires, he’s left to bleed out and ponder his life regrets while teetering on the brink of death. (“Garfield, maybe?") Heartbreaking as it sounds to watch the great Bill Murray die, he goes out with his iconic humor still intact.
Related:The Best Zombie Comedy Movies That Are Really Funny
6. Uncut Gems (2019)
Adam Sandler surprised viewers with his gritty performance inUncut Gemsas a jeweller and gambling addict who conducts his business like a gangster. But the high-wire, neon-lit thriller flick also stars former NBA MVPKevin Garnettas an obsessed, hyperbolic version of himself.
Amar’e Stoudemire, Kobe Bryant, and Joel Embiid were all considered for the role during the arduously long pre-production phase, but we’re glad they settled on Garnett for his fiery portrayal of a gem fanatic.
When Garnett shows up to Howard Ratner’s (played by Adam Sandler) New York City jewellery store, he insists on getting hold of a precious opal for good luck with his game.
Related:The Best Movies About Gambling and Casinos, Ranked
5. Harold & Kumar Go to White Castle (2004)
Neil Patrick Harrisdoesn’t just appear in one of theHarold & Kumarmovies. He appears in all three of them!
The running gag involves Harris randomly appearing at points throughout the movie franchise, and he’s painted as both a heavy drug user and complete womanizer.
Ironically, Harris didn’t come out as gay until 2006, meaning his playboy persona had to be changed in the third movie to reveal that he was only “pretending” to be straight. His real-life partner David Burtka also makes a self-referential cameo.
Even when Harris isn’t on screen, the other characters are talking about him. His extreme drug-induced personality was so loved by fans that the writers considered making a spin-off movie dedicated to him, but nothing seems to have come to fruition yet.
Related:The Best Movies About Stoners and Potheads, Ranked
4. I’m Still Here (2010)
Casey Affleck’s mockumentary spoofI’m Still Herebasically recordedJoaquin Phoenix’s public breakdown… or so viewers have suspected.
When director Casey Affleck was asked during press conferences and interviews if the film was real or a hoax, he skirted around the edges of a solid answer. The actor himself was reported to laugh throughout an entire screening. But is it actually funny? Or sort of tragic?
The candidly filmed movie follows Phoenix after he announces his “retirement” from acting, complete with chain-smoking and a scraggly beard as he attempts to break into the hip-hop industry.
Joaquin Phoenix had checked himself into rehab five years earlier, and has continued to build an impressive filmography since the release ofI’m Still Here. Therefore, it’s hard to say how much of his hard-partying spiral was real and how much of it was fake.
3. This Is the End (2013)
This Is the Endis special because it doesn’t just feature one celebrity cameo. It doesn’t even feature a handful of them.
The entire castofThis Is the Endplays comedic versions of themselves as they attend a house party at James Franco’s house. You’ll spot familiar faces like Emma Watson, Michael Cera, Channing Tatum, Kevin Hart, Rihanna… the whole lot! And they’re all playing themselves.
When the apocalypse suddenly strikes, Franco and his usual co-star buddies—Seth Rogen, Jonah Hill, Danny McBride, etc.—end up stuck in his Los Angeles home, trying to survive.
The outrageous humor ofThis Is the Endis accentuated by the fact that everyone’s playing themselves (some more exaggerated than others) and how they would supposedly act during such an event.
This Is the Endwas Rogen and Evan Goldberg’s directorial debut, and it was a feature-length adaptation of the hilarious 2007 short filmJay and Seth Versus the Apocalypse. Anything with Seth Rogen is bound to make us laugh, but him playing himself is a double win.
Related:The Best Post-Apocalyptic Movies After the End of the World
2. The Unbearable Weight of Massive Talent (2022)
The most recently released movie on this list starsNicolas Cageas the washed-up actor trying to revive his career stereotype.
Tom Gormican’s witty and action-packed comedy unfolds at a mansion in Mallorca, where Cage is the guest of honor for a billionaire playboy cinephile. Cage only takes up the offer because his work has dried up, but what he doesn’t expect is to end up being a spy for the CIA.
The Unbearable Weight of Massive Talentis the most meta and self-aware movie you’ll see this year. Cage and his host Javi Gutierrez (played by Pedro Pascal) come up with a script while on acid, and it’s the same script that ends up playing out in the film.
It’s clever, it’s funny, and it’s got lots of great Nicolas Cage. What more could you ask for?
Related:The Best Movies With Imaginary Friends and Characters
1. Being John Malkovich (1999)
If you like anything surrealist, this movie will be right up your alley. Spike Jonze’s bizarre dark comedyBeing John Malkovichis the ultimate satire movie, starringJohn Malkovich(obviously).
And it’s not just the American actor who plays himself in this one. John Cusack also plays John Malkovich, too! Let me explain:
Craig Schwartz (John Cusack) is an unemployed puppeteer who takes up a new job at an unusually low-ceilinged office.
Soon enough, he stumbles upon a secret door that’s actually a portal into the mind and body of John Malkovich. After 15 minutes, you’re ejected onto the New Jersey Turnpike. Weird, huh?
And the craziest part is when Malkovich himself goes through the portal, only to end up in a warped dimension where everyone around him—the waiters, the diners, the women—all look like him and can only say the word “Malkovich” over and over again.
Read next:The Best Examples of Surrealism in Movies, Explained
