Movies like You Can't Win (1948)
The best movies like You Can't Win (1948) are Louis C.K.: Ridiculous (2026), Adam Sandler: Love You (2024) and Ricky Gervais: Out of England 2 (2010). If You Can't Win hooked you with its comedy, these 20 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedJohn Mulaney: Kid Gorgeous at Radio City (2018)7.9/10 from 259 votes
- NewestLouis C.K.: Ridiculous (2026)Released 2026
Louis C.K.: Ridiculous (2026)
From a bee getting shot in New York City to paying strangers to take his aging father, Louis C.K. unleashes the ridiculous thoughts in his mind.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisAdam Sandler: Love You (2024)
Adam Sandler hits the stage for a thrillingly unpredictable comedy special featuring songs, jokes, party-crashing dogs and plenty of love.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisRicky Gervais: Out of England 2 (2010)
The comic performs at the Chicago Theatre.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisRicky Gervais: Armageddon (2023)
Ricky Gervais dishes out controversial takes on political correctness and oversensitivity in a taboo-busting comedy special about the end of humanity.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisDie Hart (2023)
Kevin Hart - playing a version of himself - is on a death-defying quest to become an action star. And with a little help from John Travolta, Nathalie Emmanuel, and Josh Hartnett - he just might pull it off.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisRicky Gervais: Mortality (2025)
Ricky Gervais tackles life, death and the state of the world in a brutally honest special that spares no topic, even his own mortality.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisGabriel Iglesias: I'm Sorry for What I Said When I Was Hungry (2016)
Hawaiian-shirt enthusiast Gabriel "Fluffy" Iglesias finds the laughs in racist gift baskets, Prius-driving cops and all-female taco trucks.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisDuplex (2003)
When a young couple buys their dream home, they have no idea what the sweet little old lady upstairs is going to put them through!
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisPlaydate (2025)
When out-of-work accountant Brian joins stay-at-home dad Jeff for a playdate with their sons, he expects a laid-back afternoon. Instead, they're chased by mercenaries, and Brian—totally unprepared—must survive one absurd obstacle after another.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisJohn Mulaney: Kid Gorgeous at Radio City (2018)
John Mulaney relays stories from his childhood and "SNL," eviscerates the value of college and laments getting older in this electric comedy special.
Why it matches: Recommended by TMDB viewers · both comedy
Absolute CinemaMovies like thisDave Chappelle: The Closer (2021)
As he closes out his slate of comedy specials, Dave takes the stage to try and set the record straight — and get a few things off his chest.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisRicky Gervais: Humanity (2018)
In his first special in seven years, Ricky Gervais slings his trademark snark at celebrity, mortality and a society that takes everything personally.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisMe Time (2022)
With his family away, a devoted stay-at-home dad enjoys his first me time in years by joining his hard-partying old friend on a wild birthday adventure.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisBill Burr: Drop Dead Years (2025)
In what might be his most personal and introspective hour yet, Bill offers hilarious takes on everything from male sadness to dating advice.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisLouis C.K.: Oh My God (2013)
Filmed at the Celebrity Theatre in Phoenix, AZ on February 15th and 16th, 2013, Oh My God is Louis C.K.'s fifth stand-up special, his first for HBO since 2007's Shameless, and his first since winning a Emmy Award for writing on his acclaimed show on FX, Louie. Performed in the round in front of a live audience, he discusses such topics as the food chain, animals, divorce, strange anecdotes, broken morality, murder and mortality.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisPete Davidson: Alive from New York (2020)
Comedian and "SNL" star Pete Davidson drops a candid and intimate stand-up special shot live in New York City.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisSarah Silverman: We Are Miracles (2013)
In her first-ever HBO solo special, Sarah Silverman takes the stage for an evening of adults-only stand-up comedy. Taped live in front of an intimate audience of 39 fans at Largo, a music and comedy club in Los Angeles, Sarah Silverman: We Are Miracles features Silverman taking aim at such subjects as cell-phone porn, crazy religions, specialty deodorants, terrible roommates, eyebrow waxing, her 19-year-old dog, Obama and Republicans, having babies, Pixar movies, the miracle of existence, and more.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisJerry Seinfeld: I'm Telling You for the Last Time (1998)
Taped for HBO in August 1998, on the final date of Jerry Seinfeld's tour appearances at New York City's Broadhurst Theater, I'm Telling You for the Last Time presents the standup comedian's so-called "final" standup, or at least his final tour with the standup material that made him famous.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisShane Gillis: Beautiful Dogs (2023)
In a rowdy stand-up set, Shane Gillis riffs on his girlfriend's Navy SEAL ex, touring George Washington's house and being bullied by an Australian Goth.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisEddie Murphy Raw (1987)
Eddie Murphy delights, shocks and entertains with dead-on celebrity impersonations, observations on '80s love, sex and marriage, a remembrance of Mom's hamburgers and much more.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like this
Like You Can't Win and something else?
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Frequently asked questions
What are the best movies like You Can't Win?
The closest matches to You Can't Win are Louis C.K.: Ridiculous (2026), Adam Sandler: Love You (2024) and Ricky Gervais: Out of England 2 (2010). Below are 17 more, each with the reason it matches.
What should I watch after You Can't Win?
Start with Louis C.K.: Ridiculous (2026), the closest match to You Can't Win.
What is the highest-rated movie like You Can't Win?
John Mulaney: Kid Gorgeous at Radio City (2018), rated 7.9/10 by 259 TMDB users.
What is the newest movie like You Can't Win?
Louis C.K.: Ridiculous (2026) is the most recent release on this list.
Are there English movies like You Can't Win?
Yes: Louis C.K.: Ridiculous (2026), Adam Sandler: Love You (2024) and Ricky Gervais: Out of England 2 (2010).
How are movies similar to You Can't Win chosen?
First come films that Trakt’s viewers watch alongside You Can't Win, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.