Movies like Millionaire Playboy (1940)
The best movies like Millionaire Playboy (1940) are Laughing Gravy (1931), Held Up (1999) and Easy Money (1983). If Millionaire Playboy hooked you with its comedy, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedCity Lights (1931)8.2/10 from 2,591 votes
- NewestLouis C.K.: Ridiculous (2026)Released 2026
Laughing Gravy (1931)
Stan and Ollie try to hide their pet dog Laughing Gravy from their exasperated, mean tempered landlord, who has a "No Pets" policy.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisHeld 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 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 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 thisThe Distinguished Gentleman (1992)
A Florida con man uses the recent death of the long time Congressman from his district, who he just happens to share a last name with, to get elected to his version of paradise, the U.S. Congress, where the money flows from lobbyists.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisAmerican Dreamer (2022)
In this winsome comedy, an entitled Economics professor pursues a tactic to buy an ailing widow’s mansion for nothing, but he quickly realizes that his seemingly foolproof strategy won’t be as easy as he thought.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisPretty Persuasion (2005)
A 15-year-old girl incites chaos among her friends and a media frenzy when she accuses her drama teacher of sexual harassment.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisOh, God! (1977)
When God appears to an assistant grocery manager as a good natured old man, the Almighty selects him as his messenger for the modern world.
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 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 thisJeff Dunham: Arguing with Myself (2006)
A recorded live performance of ventriloquist Jeff Dunham portrays a comedian whose revival of an old-fashioned art has made ventriloquism more relevant to modern societal concerns. Starring his six main characters, from Bubba Jay, a Nascar-obsessed hick, to Peanut, a flamboyant gay monkey, Dunham’s puppets have dirty but inoffensive senses of humor that mock the American Dream.
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 thisTillie's Punctured Romance (1914)
A womanizing city man meets Tillie in the country. When he sees that her father has a very large bankroll for his workers, he persuades her to elope with him.
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 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 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
Popcorn FlickMovies 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 this21 & Over (2013)
Brilliant student Jeff Chang has the most important interview of his life tomorrow. But today is still his birthday, what starts off as a casual celebration with friends evolves into a night of debauchery that risks to derail his life plan.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisPrivate Valentine: Blonde & Dangerous (2008)
When fluffy, bubble gum movie star Megan Valentine suddenly finds herself broke and humiliated in the public eye, she wanders from the wreckage of a car accident and witlessly enlists in the U.S. Army hoping in vain that it will change her life.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe Super (1991)
Louie Kritski is a heartless landlord who has been so negligent in keeping up his ghetto apartment that he is threatened with jail time. The judge gives him another option -- he must live in his rat-infested hell hole until he brings it up to liveable standards.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisCity Lights (1931)
A tramp falls in love with a beautiful blind flower girl. His on-and-off friendship with a wealthy man allows him to be the girl's benefactor and suitor.
Why it matches: Similar story and style · both comedy
Absolute CinemaMovies like thisFantomas vs. Scotland Yard (1967)
In the third and final episode of the trilogy, Fantômas imposes a head tax on the rich, threatening to kill those who do not comply.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisA Few Days with Me (1988)
After being discharged from a mental institution, a man is tasked by his mother to revive a struggling supermarket in Limoges. He must navigate unexpected responsibilities and the challenges of managing the store's staff.
Why it matches: Similar story and style · both comedy
SnoozefestMovies like thisI Love You, Baby (2000)
The crook couple Peter and Gwen have run away from Germany and are dreaming of a sweet life on Mallorca. During a break-in at the villa of multimillionaire Walter Ekland, Peter discovers by chance that the old man is using a detective agency to find his son, who was given up for adoption years ago. Ekland has never seen his supposed last family member and heir and therefore does not know that he has long since died. Peter sees the great opportunity of a lifetime. He assumes the identity of the lost son in order to get his hands on the big money. But the unscrupulous Decker, a private detective who was tasked with finding Ekland's real son, discovers the fraud and blackmails Gwen and Peter...
Why it matches: Similar story and style · both comedy
Trading Places (1983)
A snobbish investor and a wily street con-artist find their positions reversed as part of a bet by two callous millionaires.
Why it matches: Similar story and style · both comedy
Worth the HypeMovies like thisEnvy (2004)
A man becomes increasingly jealous of his friend's newfound success.
Why it matches: Similar story and style · both comedy
SnoozefestMovies like thisBreakfast at Tiffany's (1961)
Holly Golightly is an eccentric New York City playgirl determined to marry a Brazilian millionaire. But when young writer Paul Varjak moves into her apartment building, her past threatens to get in their way.
Why it matches: Similar story and style · both comedy
Worth the HypeMovies like thisPretty Woman (1990)
Vivian is a carefree, streetwise diamond in the rough when she meets sophisticated billionaire Edward in a chance encounter that turns into a week-long business arrangement. But Vivian's energetic spirit challenges Edward's no-nonsense approach to life, and soon they are teaching each other – and falling in love!
Why it matches: Similar story and style · both comedy
Worth the HypeMovies like thisThe Big Lebowski (1998)
Jeffrey 'The Dude' Lebowski, a Los Angeles slacker who only wants to bowl and drink White Russians, is mistaken for another Jeffrey Lebowski, a wheelchair-bound millionaire, and finds himself dragged into a strange series of events involving nihilists, adult film producers, ferrets, errant toes, and large sums of money.
Why it matches: Similar story and style · both comedy
Absolute CinemaMovies like thisPillow Talk (1959)
Playboy songwriter Brad Allen's succession of romances annoys his neighbor, interior designer Jan Morrow, who shares a telephone party line with him and hears all his breezy routines. After Jan unsuccessfully lodges a complaint against him, Brad sets about to seduce her in the guise of a sincere and upstanding Texas rancher. When mutual friend Jonathan discovers that his best friend is moving in on the girl he desires, however, sparks fly.
Why it matches: Similar story and style · both comedy
Worth the HypeMovies like this
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Frequently asked questions
What are the best movies like Millionaire Playboy?
The closest matches to Millionaire Playboy are Laughing Gravy (1931), Held Up (1999) and Easy Money (1983). Below are 27 more, each with the reason it matches.
What should I watch after Millionaire Playboy?
Start with Laughing Gravy (1931), the closest match to Millionaire Playboy.
What is the highest-rated movie like Millionaire Playboy?
City Lights (1931), rated 8.2/10 by 2,591 TMDB users.
What is the newest movie like Millionaire Playboy?
Louis C.K.: Ridiculous (2026) is the most recent release on this list.
Are there English movies like Millionaire Playboy?
Yes: Laughing Gravy (1931), Held Up (1999) and Easy Money (1983).
How are movies similar to Millionaire Playboy chosen?
First come films that Trakt’s viewers watch alongside Millionaire Playboy, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.