10 Stars Who Poked Fun at Their Own Careers on Screen

Actors often take their craft seriously, but some have the guts to laugh at themselves on screen. Whether it’s poking fun at their typecasting or past flops, these stars embrace self-mockery with charm and wit, making their performances all the more memorable.

Here are 10 actors who cleverly mocked their own careers in movies or shows, blending humor with their real-life personas. I was amazed by how they turned their Hollywood journeys into comedic gold without missing a beat.

Ryan Reynolds

Ryan Reynolds leans into his action-hero image in ‘Deadpool’ (2016) and ‘Deadpool 2’ (2018), playing Wade Wilson, who mocks his own roles in ‘Green Lantern’ (2011) and ‘X-Men Origins: Wolverine’ (2009). The films follow the wise-cracking mercenary’s chaotic adventures.

Reynolds’ self-aware jabs, like calling himself a “failed lantern,” had me laughing hard. His ability to roast his own missteps while owning the screen makes Deadpool’s humor feel personal and sharp.

George Clooney

George Clooney takes a swipe at his early career in ‘Ocean’s Twelve’ (2004), where his character, Danny Ocean, plans a heist while joking about his “cheesy” past roles. The film continues the crew’s global caper antics.

Clooney’s charm sells the self-deprecation, and I didn’t catch the nod to his ‘90s TV days at first. His subtle humor about his heartthrob image adds a layer of fun to the slick sequel.

Johnny Depp

In ‘21 Jump Street’ (2012), Johnny Depp cameos as his old TV character Tom Hanson, poking fun at his ‘80s teen idol days from the show ‘21 Jump Street’ (1987-1991). The movie follows cops infiltrating a high school.

Depp’s brief role is a hilarious nod to his past, complete with retro vibes. I was caught off guard by how gleefully he mocked his younger self, making the cameo a standout moment.

Brad Pitt

Brad Pitt plays a washed-up stuntman, Cliff Booth, in ‘Once Upon a Time in Hollywood’ (2019), subtly mocking his own aging heartthrob status. The film tracks a fading actor and his loyal stunt double in 1960s Hollywood.

Pitt’s laid-back performance winks at his own career arc, and I loved how he leaned into the irony. His cool, self-aware vibe makes the character feel like a playful reflection of himself.

Ben Affleck

Ben Affleck roasts his own career in ‘Jay and Silent Bob Strike Back’ (2001), playing himself as a cocky actor who jokes about his ‘90s rom-coms and ‘Daredevil’ (2003). The comedy follows two stoners chasing a movie deal.

Affleck’s over-the-top arrogance had me in stitches, especially his digs at his own cheesy roles. I didn’t expect him to lean so hard into the humor, making his cameo a perfect self-burn.

Robert Downey Jr.

In ‘Tropic Thunder’ (2008), Robert Downey Jr. plays Kirk Lazarus, an actor so intense he “goes method” for a role, poking fun at Downey’s own wild ‘90s reputation. The satire follows actors lost in a jungle shoot.

Downey’s outrageous performance, complete with a fake accent, nails the absurdity of his past. I was too busy laughing to notice how much he was mocking his own comeback story.

Neil Patrick Harris

Neil Patrick Harris plays a deranged version of himself in ‘Harold & Kumar Go to White Castle’ (2004) and its sequels, mocking his clean-cut ‘Doogie Howser, M.D.’ (1989-1993) image. The films follow two friends on a wild burger quest.

Harris’ unhinged, party-crazed persona is a total flip from his TV days, and I loved the shock value. His willingness to trash his wholesome past makes the role hilarious.

Matt Damon

Matt Damon cameos as a smug actor in ‘EuroTrip’ (2004), singing a ridiculous song and mocking his clean-cut ‘Bourne Identity’ (2002) persona. The teen comedy tracks a group’s European misadventure.

Damon’s goofy, bald-cap look and over-the-top performance caught me off guard. I didn’t expect him to poke fun at his serious action-star image so boldly, but it’s a perfect comedic jab.

Keanu Reeves

In ‘Always Be My Maybe’ (2019), Keanu Reeves plays an exaggerated version of himself, a pompous action star who name-drops his own films like ‘The Matrix’ (1999). The rom-com follows childhood friends reconnecting.

Reeves’ self-parody, complete with slow-motion entrances, had me cracking up. I was amazed by how he leaned into his larger-than-life persona, making the cameo a brilliant send-up of his career.

Adam Sandler

Adam Sandler mocks his string of goofy comedies in ‘Funny People’ (2009), playing a comedian whose career mirrors Sandler’s own, complete with jabs at his silly blockbusters. The film explores fame and redemption.

Sandler’s self-aware performance blends humor with surprising depth. I didn’t realize how much he was roasting his own filmography until the credits rolled, making the movie feel like a cheeky confession.

Which actor’s self-mockery made you laugh hardest, or did I miss a great one? Share your thoughts in the comments!