Surprise cameos add an extra layer of entertainment to movies by providing viewers with an unexpected source of joy they often couldn't have predicted. Even when people know who'll make the cameo, like with cameos in Deadpool & Wolverine, but no one could have predicted every cameo, and some of them eventually took fans and the Internet by storm.
Yet the best experience with cameos occurs when a character who's not supposed to be present or an actor who's not remotely attached to a project suddenly makes a surprise appearance. While it was known that Michael Keaton would be reprising his role as Bruce Wayne in The Flash, no one knew about George Clooney's cameo beforehand. It's a particularly entertaining moment as a gimmicky callback in an otherwise boring and poorly made-film. In fact, it was so surprising that people began theorizing about Clooney being the new Batman for the DCU.
15 Johnny Depp In 21 Jump Street (2012)
Reprised His Role From The TV Show
While his role as the titular character in Edward Scissorhands is considered his breakout performance, Johnny Depp achieved a leap forward in his career a few years before its release, playing one of the main characters in a uniquely premised police procedural for four years. When it was announced that there would be a 21 Jump Street movie, there was speculation about Depp making an appearance. Nothing was confirmed and his appearance in a hilariously violent scene came as a surprise cameo to fans of 21 Jump Street.
14 David Bowie In Zoolander (2001)
Played Himself
Given the premise of Zoolander, it's unsurprising that pop stars, fashion icons, and Hollywood movie stars would appear as themselves in the film. Given how much David Bowie's persona is about making fashion statements, it's even less surprising for him to make an appearance. However, he isn't credited, and first-time viewers previously unaware of his cameo are always taken aback. Bowie smoothly appears out of nowhere and leaves an unforgettable mark on the film. Zoolander, despite its current cult fandom, was a decidedly unserious B-movie at the time of production, and Bowie's participation somewhat legitimized it.
13 Tom Cruise In Tropic Thunder (2008)
Played Les Grossman
Tom Cruise always does his own stunts, on location, without any real safety precautions beyond what his character in a film would realistically do. So, a film about an action movie director obsessed with eliciting realistic performances from his actors away from the safety of a set seems perfect for a Cruise cameo.

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It'd have made perfect sense for him to appear as himself, as many industry regulars and hall-of-farmers do the same. Instead, he's unrecognizable as a film executive who smokes cigars, screams orders, and dances awkwardly.
12 Michael Jackson In Men in Black II (2002)
Played Agent M
The franchise Men in Black features many alien celebrity cameos, but perhaps the one with the most interesting backstory is that of Agent M, played by Michael Jackson. Apparently, Jackson loved the first Men in Black so much, that he requested to be in the film as a fan. The director offered him an alien cameo, like the celebrities in the first film, but he wanted to wear a black suit, so he was instead cast as Agent M. Agent M isn't confirmed to be extraterrestrial, but regardless, the 15-second cameo is unforgettable simply because of his haircut.
11 Carrie Fisher In Scream 3 (200)
Played Bianca Burnette
The Scream films are self-aware and sometimes, extremely meta, with characters in the latest film discussing the Ghostface killings like they know they are in a movie. Scream 3 goes the furthest in that direction, albeit to its detriment, by basing the story around a film crew. However, as a silver lining, it presents Carrie Fisher with the opportunity to make a meta cameo as a woman who is bitter about not being cast as Princess Leia in the world of the film. Watching Carrie Fisher in Scream 3 roast herself reminds one of how funny she was.
10 Brad Pitt In Deadpool 2 (2018)
Played Vanisher
While Deadpool & Wolverine is chock-full of references and cameos, the funniest cameo in a Deadpool movie is in the second one. It's not surprising for an A-lister to make a blink-and-you-miss cameo, but it's hilarious when there's an actual role involved, and the cameo is still only for two seconds. Brad Pitt and Ryan Reynolds' collaboration also led to Reynolds making an equally short appearance in Pitt's film Bullet Train (via SlashFilm). Both are David Leitch films, and Reynolds' cameo was also a well-hidden inside joke that surprised viewers.
9 Chris Evans In Free Guy (2021)
Played Himself
As far as cameos of actors playing themselves go, Chris Evans' blink-and-you-miss appearance in Free Guy is particularly funny because it involves his most popular role in a way that blurs the line between him and the character. The whole world watches Guy suddenly bring out Captain America's shield. It's revealed that Evans has been watching too, and he almost spits out his coffee. His minimal reaction doesn't clarify if he's happy that Guy used his character's shield or if he's offended that Guy used the shield because Evans secretly believes he's Cap himself.
8 Mike Tyson In The Hangover (2009)
Played Himself
The Hangover follows no rules. Be it the characters who break a lot of laws, or the director who throws out narrative conventions when deg the story, no one seems to believe order is important. So, when Mike Tyson randomly appears as himself, it makes sense.

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One of the best moments in the entire trilogy is the characters waking up to find a tiger in their hotel bathroom. The reveal that it belongs to Mike Tyson, who then shows up, punches Zach Galifianakis' character, plays amazing air drums, and then sings in the next film as well, only makes it funnier.
7 Bruce Willis In Ocean's Twelve (2004)
Played Himself
Steven Soderbergh's follow-up to his most famous heist movie is also his most meta work. Julia Roberts plays a character who pretends to be Julia Roberts herself in the world of the film. To make things more interesting, she has a friend in the movie, played by Bruce Willis, who is the actor Bruce Willis. This isn't an alternate version of Willis within the film's setting. So, even though it's clear that the celebrity world plays a big part in the heist drama, Willis' cameo in Ocean's Twelve is unexpected due to the meta-level on which Roberts' character exists.
6 Jimmy Buffett In Jurassic World (2015)
Played A Bartender
In one of the most hilarious meta jokes in recent movie history, Jimmy Buffett's cameo in Jurassic World pays tribute to his music career. Jurassic World isn't a movie where celebrity cameos would be expected, as the franchise has a different set of selling points, mainly founded upon massive spectacle and the scientists behind the revival of dinosaurs facing the consequences of their actions. But the "Margaritaville" singer does something uniquely comical, which makes his cameo in Jurassic World unforgettable. When dinosaurs are wreaking havoc and everyone's prioritizing self-preservation, Buffet plays a bartender who saves margaritas from spilling.