Movies like Painting the Town (1927)
The best movies like Painting the Town (1927) are Gabriel Iglesias: I'm Sorry for What I Said When I Was Hungry (2016), Steve Martin and Martin Short: An Evening You Will Forget for the Rest of Your Life (2018) and The Errand Boy (1961). If Painting the Town 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
Gabriel 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 thisSteve Martin and Martin Short: An Evening You Will Forget for the Rest of Your Life (2018)
Comedians and writers Steve Martin and Martin Short perform a live comedy set with music by The Steep Canyon Rangers and jazz pianist, Jeff Babko, at the Peace Center in Greenville, South Carolina.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe Errand Boy (1961)
Paramutual Pictures wants to know where all the money is going so they hire Morty to be their spy. Morty works for Mr. Sneak and gets a job in the mail room so that he can have access to the lot. But all that Morty ever finds is that he can cause havoc no matter what he does.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies 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 thisClear History (2013)
Nathan Flomm, in order to avoid the humiliation of having missed out on a hugely successful business, assumes a new identity on Martha's Vineyard. He plots revenge when his former business partner moves to the same town.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies 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 thisThe Horse's Mouth (1958)
Gulley Jimson is a boorish aging artist recently released from prison. A swindler in search of his next art project, he hunkers down in the penthouse of would-be patrons the Beeders while they go on an extended vacation; he paints a mural on their wall, pawns their valuables and, along with the sculptor Abel, inadvertently smashes a large hole in their floor. Jimson's next project is an even larger wall in an abandoned church.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisGabriel Iglesias: Aloha Fluffy (2013)
ALOHAAAAA! Internationally acclaimed comedian, Gabriel Iglesias, returns to Comedy Central with his latest stand-up special taped at Honolulu’s Hawaii Theatre Center. Watch as Fluffy brings the house down yet again in this complete special with his unique and animated show that has made him popular among fans of all ages. Aloha Fluffy is sure to be a comedy classic, making this extended and uncensored special a must-own.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisJerry Seinfeld: 23 Hours to Kill (2020)
Jerry Seinfeld takes the stage in New York and tackles talking vs. texting, bad buffets vs. so-called "great" restaurants and the magic of Pop Tarts.
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 thisThunderstruck (2012)
After NBA star Kevin Durant switches talent with 16 year old Brian, the teenager becomes the star of his high school team, but Durant starts struggling and eventually learns an important lesson.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies 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 thisThe Happiest Days of Your Life (1950)
Nutbourne College, an old established, all-boys, boarding school is told that another school is to be billeted with due to wartime restrictions. The shock is that it's an all-girls school that has been sent. The two head teachers are soon battling for the upper hand with each other and the Ministry. But a crisis (or two) forces them to work together.
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 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 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 thisDave Chappelle: The Unstoppable... (2025)
Facing a world gone sideways, comedy icon Dave Chappelle delivers bold truths and potent punchlines in this no-holds-barred special.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisNo Time for Sergeants (1958)
Georgia farm boy Will Stockdale is about to bust with pride. He’s been drafted. Will’s ready. But is Uncle Sam ready for Will?
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies 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 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
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Frequently asked questions
What are the best movies like Painting the Town?
The closest matches to Painting the Town are Gabriel Iglesias: I'm Sorry for What I Said When I Was Hungry (2016), Steve Martin and Martin Short: An Evening You Will Forget for the Rest of Your Life (2018) and The Errand Boy (1961). Below are 17 more, each with the reason it matches.
What should I watch after Painting the Town?
Start with Gabriel Iglesias: I'm Sorry for What I Said When I Was Hungry (2016), the closest match to Painting the Town.
What is the highest-rated movie like Painting the Town?
Louis C.K.: Oh My God (2013), rated 7.6/10 by 229 TMDB users.
What is the newest movie like Painting the Town?
Louis C.K.: Ridiculous (2026) is the most recent release on this list.
Are there English movies like Painting the Town?
Yes: Gabriel Iglesias: I'm Sorry for What I Said When I Was Hungry (2016), Steve Martin and Martin Short: An Evening You Will Forget for the Rest of Your Life (2018) and The Errand Boy (1961).
How are movies similar to Painting the Town chosen?
First come films that Trakt’s viewers watch alongside Painting the Town, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.