Movies like Rich and Carefree (1957)
The best movies like Rich and Carefree (1957) are Chief Daddy 2: Going for Broke (2021), Fun with Dick and Jane (1977) and Family Plot (1976). If Rich and Carefree hooked you with its comedy, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedChickenhare and the Hamster of Darkness (2022)7.2/10 from 299 votes
- NewestLouis C.K.: Ridiculous (2026)Released 2026
Chief Daddy 2: Going for Broke (2021)
The Beecroft family are ready to spend all of Chief Daddy's inheritance, but not if the CEO of his company has anything to do with it.
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 thisFamily Plot (1976)
Spiritualist Blanche Tyler and her cab-driving boyfriend encounter a pair of serial kidnappers while trailing a missing heir in California.
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 thisWake Up, Ron Burgundy: The Lost Movie (2004)
While Ron Burgundy's rivalry with Veronica Corningstone escalates quickly, a group of unprofessional thieves better known as 'The Alarm Clock' try to make the truth known, whatever that may mean...
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 thisTill Luck Do Us Part (2012)
Check out the hilarious story of luck and misadventures of Tino, a family man whose life is transformed after he wins the lottery. Dazzled by wealth, this boaster spends all his money on a life of luxury and ostentation. But after finding out that he is bankrupt, he faces comical situations: besides not telling his wife he is broke because she is pregnant and cannot get upset, Tino must accept help from his neighbor who is an extremely thrifty financial adviser and the only one capable of getting him out of the rut.
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 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 thisCarry On Regardless (1961)
After a bunch of no-hopers approaches an employment agency, the anarchy mounts as they do a series of odd jobs, including a chimp's tea party, trying to stay sober at a wine tasting… and demolishing a house.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisOscar (1991)
Angelo "Snaps" Provolone made his dying father a promise on his deathbed: he would leave the world of crime and become an honest businessman. Despite having no experience in making money in a legal fashion, Snaps sets about to keep his promise.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies 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 thisBig Trouble (2002)
The story of how a mysterious suitcase brings together, and changes, the lives of a divorced dad, an unhappy housewife, two hitmen, a pair of street thugs, two love struck teens, two FBI men and a psychedelic toad. Based on Pulitzer Prize-winning humorist Dave Barry's best-selling first novel, "Big Trouble."
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisChickenhare and the Hamster of Darkness (2022)
A brave young animal explorer teams up with two trusty friends to find a powerful artifact before his greedy uncle can get his paws on it.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisEenie Meanie (2025)
A former teenage getaway driver gets dragged back into her unsavory past when a former employer offers her a chance to save the life of her chronically unreliable ex-boyfriend.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisVai Que Dá Certo (2013)
5 friends have a plan to rob a transporter that can change their lives.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisCa$h (2010)
A stroke of good luck turns lethal for Sam Phelan and his wife Leslie when they are faced with a life-changing decision that brings strange and sinister Pyke Kubic to their doorstep. As Pyke leads Sam and Leslie on a tumultuous adventure through the streets of Chicago, each are pulled deeper and deeper into a desperate spiral of deception and violence – all in the name of money.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisAccident Man (2018)
Mike Fallon, the Accident Man, is a stone cold killer. When a loved one is murdered by his own crew, Fallon is forced to avenge the one person who actually meant something to him.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisStretch (2014)
A hard-luck limo driver struggling to go straight and pay off a debt to his bookie takes on a job with a crazed passenger whose sought-after ledger implicates some seriously dangerous criminals.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe Family Jewels (1965)
A young heiress must choose between six uncles, one of which is up to no good and out to harm the girl's beloved bodyguard who practically raised her.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisUm Candango na Belacap (1961)
During the inauguration of Brasília, Brazil's brand new capital city, singer and ballerina Gilda hides in a working-class night club to escape from an inconvenient millionaire who's trying to date her.
Why it matches: Similar story and style · both comedy
O Camelô da Rua Larga (1958)
Why it matches: Similar story and style · both comedy
Barnabé, You Are Mine (1952)
A cleaner accidentely stills a secret formula and get mistaken for the heir prince of an old kingdom.
Why it matches: Similar story and style · both comedy
Tererê Não Resolve (1938)
Three couples, two already living in Rio; and the third, with 'the one who hates carnival', coming to visit an aunt. One of the women bets that all husbands are unfaithful. They send invitations to their husbands to the carnival ball. They find a pretext to be able to attend. They, in turn, go in disguise, just like the maid. Hence the confusion at the ball, each one dating the other's wife.
Why it matches: Similar story and style · both comedy
Minha Sogra é da Polícia (1958)
Why it matches: Similar story and style · both comedy
O Petróleo é Nosso (1954)
A lady, owner of a large area of land where it is believed there are several oil wells, is almost fooled by the president of a pseudo petroleum company into giving up her property for nothing, but is saved by his son's noble intervention.
Why it matches: Similar story and style · both comedy
Like Rich and Carefree and something else?
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Frequently asked questions
What are the best movies like Rich and Carefree?
The closest matches to Rich and Carefree are Chief Daddy 2: Going for Broke (2021), Fun with Dick and Jane (1977) and Family Plot (1976). Below are 27 more, each with the reason it matches.
What should I watch after Rich and Carefree?
Start with Chief Daddy 2: Going for Broke (2021), the closest match to Rich and Carefree.
What is the highest-rated movie like Rich and Carefree?
Chickenhare and the Hamster of Darkness (2022), rated 7.2/10 by 299 TMDB users.
What is the newest movie like Rich and Carefree?
Louis C.K.: Ridiculous (2026) is the most recent release on this list.
How are movies similar to Rich and Carefree chosen?
First come films that Trakt’s viewers watch alongside Rich and Carefree, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.