Movies like Penny Paradise (1938)
The best movies like Penny Paradise (1938) are Easy Money (1983), The Million Pound Note (1954) and Fun with Dick and Jane (1977). If Penny Paradise hooked you with its comedy, these 20 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedEddie Murphy Raw (1987)7.2/10 from 394 votes
- NewestLouis C.K.: Ridiculous (2026)Released 2026
Easy 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 thisThe Million Pound Note (1954)
An impoverished American sailor is fortunate enough to be passing the house of two rich gentlemen who have conceived the crazy idea of distributing a note worth one million pounds. The sailor finds that whenever he tries to use the note to buy something, people treat him like a king and let him have whatever he likes for free. Ultimately, the money proves to be more troublesome than it is worth when it almost costs him his dignity and the woman he loves.
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 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 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 thisAnuvahood (2011)
Kenneth (who likes to call himself Kay) begins to realise he's just another wannabe bad boy... even less than a loser in fact. After quitting his job at Laimsbury's, Kay vows to become a respected gangster... or cry trying. A pulls-no-punches, coming-of-age story, centering on one directionless hopeless "shotter", who finds his true worth in the face of urban adversity.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisFunny Bones (1995)
Tommy Fawkes wants to be a successful comedian. After his Las Vegas debut is a failure, he returns to Blackpool where his father—also a comedian—started, and where he spent the summers of his childhood.
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 thisEddie Murphy Raw (1987)
Eddie Murphy delights, shocks and entertains with dead-on celebrity impersonations, observations on '80s love, sex and marriage, a remembrance of Mom's hamburgers and much more.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies 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
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 thisIliza Shlesinger: Confirmed Kills (2016)
The standup sensation tackle's TV's "Shark Tank," what it means to be a woman and how to deal with the lawless party goblin that lives in us all.
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 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 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 Twelve Chairs (1970)
In 1920s Soviet Russia, a fallen aristocrat, a priest and a con artist search for a treasure of jewels hidden inside one of twelve dining chairs, lost during the revolution.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisDylan Moran: Like, Totally (2006)
Dylan Moran returns with an all-new stand-up show. Unpredictable, startling, bizarre, elegiac, but above all brilliant and hilariously funny, Moran is a master of comedy.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisThe Luck of the Irish (2001)
A teenager must battle for a gold charm to keep his family from being controlled by an evil leprechaun.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisBeverly Hills Chihuahua 2 (2011)
Puppy mayhem turns the lives of newlywed Chihuahua parents Papi and Chloe upside down when their rambunctious, mischievous puppies present one challenge after another. But when their human owners end up in trouble, the tiny pups will stop at nothing to save them - because in good times and hard times, the family always sticks together. So Papi, Chloe and the puppies embark on a heroic adventure, proving once again that big heroes come in small packages.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies 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 this
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Frequently asked questions
What are the best movies like Penny Paradise?
The closest matches to Penny Paradise are Easy Money (1983), The Million Pound Note (1954) and Fun with Dick and Jane (1977). Below are 17 more, each with the reason it matches.
What should I watch after Penny Paradise?
Start with Easy Money (1983), the closest match to Penny Paradise.
What is the highest-rated movie like Penny Paradise?
Eddie Murphy Raw (1987), rated 7.2/10 by 394 TMDB users.
What is the newest movie like Penny Paradise?
Louis C.K.: Ridiculous (2026) is the most recent release on this list.
Are there English movies like Penny Paradise?
Yes: Easy Money (1983), The Million Pound Note (1954) and Fun with Dick and Jane (1977).
How are movies similar to Penny Paradise chosen?
First come films that Trakt’s viewers watch alongside Penny Paradise, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.