Movies like Outdoor Pajamas (1924)
The best movies like Outdoor Pajamas (1924) are Held Up (1999), Jimmy O. Yang: Good Deal (2020) and Fun with Dick and Jane (1977). If Outdoor Pajamas hooked you with its comedy, these 20 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedRicky Gervais: Armageddon (2023)7.1/10 from 243 votes
- NewestDave Chappelle: The Unstoppable... (2025)Released 2025
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 thisJimmy O. Yang: Good Deal (2020)
In his debut standup special, Good Deal, Jimmy will tell you all about his take on Asian representation, how he learned to speak English from rap videos, dating tall women, and pursuing his dreams only to disappoint his old school Chinese parents. From assimilation to representation, Jimmy O. Yang delivers an absolutely hilarious hour of comedy in Good Deal.
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 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 thisJimmy Carr: His Dark Material (2021)
Jimmy Carr finds humor in the darkest of places in this stand-up special that features his dry, sardonic wit — and some jokes he calls "career enders."
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies 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 thisThe Wedding Year (2019)
A commitment-phobic 27-year old’s relationship is put to the test when she and her boyfriend attend 7 weddings in the same year.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisChris Rock: Never Scared (2004)
Chris Rock, the three-time Emmy Award-winner, comedian, actor, and host of HBO's acclaimed The Chris Show, stars in his fourth solo stand-up special for HBO, Chris Rock: Never Scared. Featuring his unique, insightful, and hilarious views on a host of social, political and, celebrity issues, Rock confirms his stature as the leading comic of our time.
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 thisJimmy Carr: Natural Born Killer (2024)
Jimmy Carr refutes the idea that you can't joke about anything these days with his edgy takes on gun control, religion, cancel culture and consent.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisChris Rock: Kill the Messenger (2008)
An HBO special edited from three performances from Chris Rock's 2008 comedy tour: London (dark suit, dark shirt), Johannesburg (black suit, white shirt) and New York (shiny jacket). Topics include the ongoing presidential campaign, the possibility of a black president, George W. Bush, gas prices, low-paid jobs, ringtones and bottled water, sex, relationships and the correct use of the n-word
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies 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 thisSextuplets (2019)
Father-to-be Alan is shocked to learn that he was born a sextuplet. With his newfound brother Russell riding shotgun, the duo sets out on a hilarious journey to reunite with their remaining long-lost siblings.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisGeorge Carlin: It's Bad for Ya! (2008)
It's Bad For Ya, Carlin's Emmy nominated 14th and final HBO special from March of 2008 features Carlin's noted irreverent and unapologetic observations on topics ranging from death, religion, bureaucracy, patriotism, overprotected children and big business to the pungent examinations of modern language and the decrepit state of the American culture.
Why it matches: Recommended by TMDB viewers · both comedy
Absolute CinemaMovies 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 thisRicky Gervais Live 2: Politics (2004)
A year after Animals, Ricky Gervais comes back with his second stand up comedy tour: Politics.
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 thisIliza Shlesinger: War Paint (2013)
Her innocent appearance is just a cover for Last Comic Standing winner Iliza Shlesinger's acerbic, stream-of-conscious comedy that she unleashes on an unsuspecting audience in her hometown of Dallas in "War Paint," her first stand-up special.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisTaking Care of Business (1990)
An uptight advertising exec has his entire life in a filofax organizer which mistakenly ends up in the hands of a friendly convict who poses as him.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisAfter the Ball (2015)
After the Ball, a retail fairy tale set in the world of fashion. Kate's dream is to design for couturier houses. Although she is a bright new talent, Kate can't get a job. No one trusts the daughter of Lee Kassell, a retail guru who markets clothes "inspired" by the very designers Kate wants to work for. Who wants a spy among the sequins and stilettos? Reluctantly, Kate joins the family business where she must navigate around her duplicitous stepmother and two wicked stepsisters. But with the help of a prince of a guy in the shoe department her godmother's vintage clothes and a shocking switch of identities, Kate exposes the evil trio, saves her father's company -- and proves that everyone can wear a fabulous dress.
Why it matches: Recommended by TMDB viewers · both comedy
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Frequently asked questions
What are the best movies like Outdoor Pajamas?
The closest matches to Outdoor Pajamas are Held Up (1999), Jimmy O. Yang: Good Deal (2020) and Fun with Dick and Jane (1977). Below are 17 more, each with the reason it matches.
What should I watch after Outdoor Pajamas?
Start with Held Up (1999), the closest match to Outdoor Pajamas.
What is the highest-rated movie like Outdoor Pajamas?
Ricky Gervais: Armageddon (2023), rated 7.1/10 by 243 TMDB users.
What is the newest movie like Outdoor Pajamas?
Dave Chappelle: The Unstoppable... (2025) is the most recent release on this list.
Are there English movies like Outdoor Pajamas?
Yes: Held Up (1999), Jimmy O. Yang: Good Deal (2020) and Fun with Dick and Jane (1977).
How are movies similar to Outdoor Pajamas chosen?
First come films that Trakt’s viewers watch alongside Outdoor Pajamas, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.