Movies like Money on the Side (2007)
The best movies like Money on the Side (2007) are Fun with Dick and Jane (1977), Taking Care of Business (1990) and The Distinguished Gentleman (1992). If Money on the Side hooked you with its comedy, these 20 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedMuch Ado About Nothing (2013)6.8/10 from 299 votes
- NewestMy Best Friend (2026)Released 2026
Fun 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 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 thisMy Best Friend (2026)
When empty nest syndrome hits, two BFFs follow their teen daughters to Portugal and find love, fun and a whole new meaning of friendship along the way.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisHead Over Heels (2010)
After being left by her husband and fired from her work, a workaholic, thirtysomething businesswoman is forced to go through a big change in her life and becomes a partner on a decadent sex shop.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe Errand Boy (1961)
Paramutual Pictures wants to know where all the money is going so they hire Morty to be their spy. Morty works for Mr. Sneak and gets a job in the mail room so that he can have access to the lot. But all that Morty ever finds is that he can cause havoc no matter what he does.
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 thisA Bad Idea Gone Wrong (2017)
Two would-be thieves forge a surprising relationship with an unexpected housesitter when they accidentally trap themselves in a house they just broke into.
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 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 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 thisGood Neighbor Sam (1964)
To help his divorced neighbor claim a substantial inheritance, a family man poses as her husband. The ruse spills over into his career in advertising, and his recent promotion relies on his wholesome and moral appearance.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisMoonwalkers (2015)
What if Apollo 11 never actually made it? What if, in reality, Stanley Kubrick secretly shot the famous images of the moon landing in a studio, working for the US administration? This is the premise of a totally plausible conspiracy theory that takes us to swinging sixties London, where a stubborn CIA agent will never find Kubrick but is forced to team up with a lousy manager of a seedy rock band to develop the biggest con of all time.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisMuch Ado About Nothing (2013)
A modern retelling of Shakespeare's classic comedy about two pairs of lovers with different takes on romance and a way with words.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisChief 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 thisI Love My Dad (2022)
A hopelessly estranged father catfishes his son in an attempt to reconnect.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisAdventures in Public School (2018)
A socially-awkward, home-schooled kid forces his way into public school against his suffocating, but loving, mother's wishes.
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 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 thisWho's Minding the Store? (1963)
Norman Phiffer, a proud man in a humble life, doesn't know that his girlfriend, Barbara, is heir to the Tuttle Department Store dynasty. Mrs. Tuttle, Barbara's mother, is determined to split the two lovers, and hires Norman in an attempt to humiliate him enough that Barbara leaves him. Will she ruin their love, or will he ruin her store?
Why it matches: Recommended by TMDB viewers · both comedy
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Frequently asked questions
What are the best movies like Money on the Side?
The closest matches to Money on the Side are Fun with Dick and Jane (1977), Taking Care of Business (1990) and The Distinguished Gentleman (1992). Below are 17 more, each with the reason it matches.
What should I watch after Money on the Side?
Start with Fun with Dick and Jane (1977), the closest match to Money on the Side.
What is the highest-rated movie like Money on the Side?
Much Ado About Nothing (2013), rated 6.8/10 by 299 TMDB users.
What is the newest movie like Money on the Side?
My Best Friend (2026) is the most recent release on this list.
How are movies similar to Money on the Side chosen?
First come films that Trakt’s viewers watch alongside Money on the Side, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.