Movies like Gypped in the Penthouse (1955)
The best movies like Gypped in the Penthouse (1955) are Held Up (1999), One Night at McCool's (2001) and Sextuplets (2019). If Gypped in the Penthouse hooked you with its comedy, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedCops (1922)7.2/10 from 242 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 thisOne Night at McCool's (2001)
On an ordinary night, in an ordinary part of town, a beautiful young woman walks into a bar. Her name is Jewel, and before long she is chatting to bartender Randy. The pair leave together, but he ends up getting into a tussle with her criminal boyfriend, who she then shoots dead, later persuading Randy to take the rap for her. But this isn't the end of it, as both Randy's cousin Carl and the detective assigned to the murder case also fall for Jewel's charms and find themselves caught up in the ensuing events. It seems that any man who meets Jewel falls instantly in love with her, and she's going to use this fully to her own advantage, leaving a trail of havoc in her wake. It also seems that she is going to get away with it - that is, until Randy decides to hire a hitman...
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies 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 thisBrain Donors (1992)
Three manic idiots—a lawyer, a cab driver and a handyman—team up to run a ballet company to fulfil the will of a millionaire. Stooge-like antics result as the trio try to outwit the rich widow and her scheming big-shot lawyer, who also wants to run the ballet.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisEasy Money (1983)
To inherit his mother-in-law's colossal fortune, a hard living gambling addict must change his unhealthy ways before it gets the best of him.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisSupport Your Local Gunfighter (1971)
A con artist arrives in a mining town controlled by two competing companies. Both companies think he's a famous gunfighter and try to hire him to drive the other out of town.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisChris Rock: Selective Outrage (2023)
Chris Rock delivers an electric stand-up set on non-racist yoga pants, spoiling his kids, the Kardashians and his thoughts on the Will Smith fiasco.
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 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 thisHannibal Buress: Comedy Camisado (2016)
He's a kamikaze gambler. A one-arm cuddler. And if his fly is down, so be it. A night of sly riffs and slow burns.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisWanda Sykes: Not Normal (2019)
Wanda Sykes tackles politics, reality TV, racism and the secret she'd take to the grave in this rollicking, no-holds-barred stand-up special.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies 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 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 thisNo Deposit, No Return (1976)
Two rich children devise a way to escape their grandfather and visit their mother. Unfortunately for two hapless safe crackers, they become part of the plan.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisLaRoy, Texas (2024)
Broke and depressed, Ray is mistaken for a dangerous hitman and given an envelope of cash. Along with his P.I. friend Skip, he must escape the actual hitman to make it out of LaRoy alive.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisMalibu Rescue: The Next Wave (2020)
It’s summer again, and everyone’s favorite Junior Rescuers, The Flounders, are back at Tower 2. With the International Junior Rescue Championships headed to Southern California, the eyes of the entire planet are on Malibu Beach. But when Team USA falls victim to a bout of food poisoning, it’s up to Tyler, Dylan, Eric, Lizzie and Gina to represent their country in the world's most extreme lifeguard challenge!
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies 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 thisMen in Black (1934)
The stooges are three doctors who graduated medical school by being in it for too many years. They come across such problems as an overly chirpy nurse, a mental patient, and a combination to a safe swallowed by the hospital superintendent in the course of their attempt to get through the day.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisMr. Bones (2001)
A medicine man is sent looking for the son of his tribal king, and brings back an American golfer and a host of goons intent on keeping him in the golf tournament.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe Three Stooges (2012)
Left on the doorstep of an orphanage run by nuns, three newborn knuckleheads grow up to be finger-poking, nyuk-nyuking janitors named Larry, Curly and Moe. When they learn that financial problems will soon force the only home they've ever known to close, the trio sets out to raise $830,000 in one month. Out in the world for the very first time, the three innocent bumblers become embroiled in a murder plot and find stardom on a TV reality show.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisThe Cactus Kid (1930)
Mickey walks into the tavern where Minnie is dancing, and begins to dance and play piano himself. Pegleg Pete comes in and treats Minnie badly. Mickey tries to defend her, but Pete steals her away. Mickey, riding Horace Horsecollar, gives chase. He manages to throw Pete off a cliff.
Why it matches: Similar story and style · both comedy
Smith's Pony (1927)
The Smith's visit San Francisco to attend a horse show only to have their precocious daughter cause some minor comical mishaps and their over-sized canine refusing to obey commands.
Why it matches: Similar story and style · both comedy
Convict 13 (1920)
A young golfer is mugged by an escaped convict and finds himself in a prison where he foils a jailbreak.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisHis Wedding Night (1917)
Al and Roscoe, employees at a gas station, are rivals for Alice. When Buster delivers a wedding gown for Alice and begins modeling it, he is mistaken for Alice and is kidnapped by Al.
Why it matches: Similar story and style · both comedy
SnoozefestMovies like thisMy Wife's Relations (1922)
Buster and a woman are mistakenly married and her initially unfriendly family begins to treat him nicely when they come to believe he has a large inheritance awaiting him.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisThe Stubborn Donkey (2008)
When the old fisherman tries to convince his donkey to climb the steep winding road of their Greek island, he finds Mariza to be one suborn ass. But the old man knows that no one can resist Zorba's dance.
Why it matches: Similar story and style · both comedy
Cops (1922)
Buster Keaton gets involved in a series of misunderstandings involving a horse and cart. Eventually he infuriates every cop in the city when he accidentally interrupts a police parade.
Why it matches: Similar story and style · both comedy
Worth the HypeMovies like thisDay Dreams (1922)
In order to impress the father of a girl he is keen on, a young man goes to the city in search of work. In his letters home he writes of his various jobs which her imagination expands into much nobler ones than those that he is actually attempting.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisHard Luck (1921)
A down on his luck young man makes several attempts at committing suicide but fails them too. He then finds himself becoming more confident through a series of petty adventures, to such an extent that this becomes his undoing.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisBack Stage (1919)
Roscoe and Buster give a bullying Strongman the what-for, but after the performance troupe quits it's up to Fatty and Buster to keep the show going.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like this
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Frequently asked questions
What are the best movies like Gypped in the Penthouse?
The closest matches to Gypped in the Penthouse are Held Up (1999), One Night at McCool's (2001) and Sextuplets (2019). Below are 27 more, each with the reason it matches.
What should I watch after Gypped in the Penthouse?
Start with Held Up (1999), the closest match to Gypped in the Penthouse.
What is the highest-rated movie like Gypped in the Penthouse?
Cops (1922), rated 7.2/10 by 242 TMDB users.
What is the newest movie like Gypped in the Penthouse?
Louis C.K.: Ridiculous (2026) is the most recent release on this list.
Are there English movies like Gypped in the Penthouse?
Yes: Held Up (1999), One Night at McCool's (2001) and Sextuplets (2019).
How are movies similar to Gypped in the Penthouse chosen?
First come films that Trakt’s viewers watch alongside Gypped in the Penthouse, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.