Movies like How to Seduce a Playboy? (1966)
The best movies like How to Seduce a Playboy? (1966) are Held Up (1999), Louis C.K.: Oh My God (2013) and Adam Sandler: Love You (2024). If How to Seduce a Playboy? hooked you with its comedy, these 20 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedLouis C.K.: Oh My God (2013)7.6/10 from 229 votes
- NewestLouis C.K.: Ridiculous (2026)Released 2026
Held Up (1999)
What should have been a romantic getaway turns into one hilarious debacle after another when Michael's woman dumps him in the desert where he gets carjacked by a teenager and he is taken hostage in a stickup at the local Sip and Zip.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies 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 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: 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 thisDriver's Ed (2026)
A group of teens hit the road in a stolen driver's ed car, racing against time to help a lovesick high school senior track down his college-freshman girlfriend and win her back.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisLouis 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 this2 Minutes of Fame (2020)
An up-and-coming stand-up comic moves to L.A. to pursue a film career after video clips of his act make him an online sensation.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe F**k-It List (2020)
After a prank blows up a studious high school senior's life, he shares a list of certain things he wishes he'd done differently — and maybe still can.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies 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 thisFun with Dick and Jane (1977)
When an upwardly mobile couple find themselves unemployed and in debt, they turn to armed robbery in desperation.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisBill Burr: Walk Your Way Out (2017)
No-nonsense comic Bill Burr takes the stage in Nashville and riffs on fast food, overpopulation, dictators and gorilla sign language.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisRicky Gervais: SuperNature (2022)
With his signature pitch-black sense of humor, Ricky Gervais takes the stage at the London Palladium in this provocative stand-up comedy special.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisThe Patsy (1964)
Eccentric bellhop Stanley Belt is recruited unexpectedly by the comedy team of a recently deceased entertainer. Stanley struggles to become a song-and-dance man as the team grooms him to become a star. But as the date of a high-stakes appearance on the Ed Sullivan Show grows near, they begin to fear that the only astonishing thing about Stanley is his utter lack of talent.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisJackass Presents: Bad Grandpa (2013)
86-year-old Irving Zisman is on a journey across America with the most unlikely companion: his 8 year-old grandson, Billy.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisA Bad Idea Gone Wrong (2017)
Two would-be thieves forge a surprising relationship with an unexpected housesitter when they accidentally trap themselves in a house they just broke into.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe Roast of Tom Brady (2024)
Offensive lines. Full-contact comedy. Kevin Hart hosts this all-star roast of NFL legend Tom Brady.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like this29th Street (1991)
After winning $6.2 million in the 1976 New York State Lottery, he is arrested for throwing rocks at a church. He then tells his story at the police station.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies 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 thisDylan Moran: Like, Totally (2006)
Dylan Moran returns with an all-new stand-up show. Unpredictable, startling, bizarre, elegiac, but above all brilliant and hilariously funny, Moran is a master of comedy.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisSeriously Single (2020)
While her free-living bestie urges her to embrace singlehood, a commitment-craving social media expert can't stop following the life of a former love.
Why it matches: Recommended by TMDB viewers · both comedy
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Frequently asked questions
What are the best movies like How to Seduce a Playboy??
The closest matches to How to Seduce a Playboy? are Held Up (1999), Louis C.K.: Oh My God (2013) and Adam Sandler: Love You (2024). Below are 17 more, each with the reason it matches.
What should I watch after How to Seduce a Playboy??
Start with Held Up (1999), the closest match to How to Seduce a Playboy?.
What is the highest-rated movie like How to Seduce a Playboy??
Louis C.K.: Oh My God (2013), rated 7.6/10 by 229 TMDB users.
What is the newest movie like How to Seduce a Playboy??
Louis C.K.: Ridiculous (2026) is the most recent release on this list.
Are there German movies like How to Seduce a Playboy??
The closest matches are in other languages.
How are movies similar to How to Seduce a Playboy? chosen?
First come films that Trakt’s viewers watch alongside How to Seduce a Playboy?, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.