Movies like The Headstrong (1970)
The best movies like The Headstrong (1970) are Fun with Dick and Jane (1977), Family Plot (1976) and Oscar (1991). If The Headstrong hooked you with its comedy, these 20 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedFamily Plot (1976)6.8/10 from 531 votes
- NewestDriver's Ed (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 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 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 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 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 Honey Pot (1967)
In Venice, a millionaire hires an actor to help him prank three greedy exes into thinking he's dying and leaving his fortune to one of them.
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 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 thisBabes (2024)
After getting pregnant from a one-night stand, a single woman leans on her married best friend and mother of two to guide her through gestation and beyond.
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 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 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 thisClear History (2013)
Nathan Flomm, in order to avoid the humiliation of having missed out on a hugely successful business, assumes a new identity on Martha's Vineyard. He plots revenge when his former business partner moves to the same town.
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 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 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 thisAfter the Ball (2015)
After the Ball, a retail fairy tale set in the world of fashion. Kate's dream is to design for couturier houses. Although she is a bright new talent, Kate can't get a job. No one trusts the daughter of Lee Kassell, a retail guru who markets clothes "inspired" by the very designers Kate wants to work for. Who wants a spy among the sequins and stilettos? Reluctantly, Kate joins the family business where she must navigate around her duplicitous stepmother and two wicked stepsisters. But with the help of a prince of a guy in the shoe department her godmother's vintage clothes and a shocking switch of identities, Kate exposes the evil trio, saves her father's company -- and proves that everyone can wear a fabulous dress.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe Pope of Greenwich Village (1984)
Charlie and his troublesome cousin Paulie decide to steal $150,000 in order to back a "sure thing" race horse that Paulie has inside information on. The aftermath of the robbery gets them into serious trouble with the local Mafia boss and the corrupt New York City police department.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisCotton Comes to Harlem (1970)
Harlem's African-American population is being ripped off by the Rev. Deke O'Malley, who dishonestly claims that small donations will secure parcels of land in Africa. When New York City police officers Gravedigger Jones and Coffin Ed Johnson look into O'Malley's scam, they learn that the cash is being smuggled inside a bale of cotton. However, the police, O'Malley, and lots of others find themselves scrambling when the money goes missing.
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
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Frequently asked questions
What are the best movies like The Headstrong?
The closest matches to The Headstrong are Fun with Dick and Jane (1977), Family Plot (1976) and Oscar (1991). Below are 17 more, each with the reason it matches.
What should I watch after The Headstrong?
Start with Fun with Dick and Jane (1977), the closest match to The Headstrong.
What is the highest-rated movie like The Headstrong?
Family Plot (1976), rated 6.8/10 by 531 TMDB users.
What is the newest movie like The Headstrong?
Driver's Ed (2026) is the most recent release on this list.
How are movies similar to The Headstrong chosen?
First come films that Trakt’s viewers watch alongside The Headstrong, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.