Movies like The Gypsy Trail (1918)
The best movies like The Gypsy Trail (1918) are Driver's Ed (2026), Held Up (1999) and Why Worry? (1923). If The Gypsy Trail hooked you with its comedy, these 30 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
Driver'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 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 thisWhy Worry? (1923)
A hypochondriac vacations in the tropics for the fresh air - and finds himself in the middle of a revolution instead.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisSon of Rambow (2007)
Will is looking for an escape from his family when he encounters Lee, the school bully. Armed with a video camera and a copy of Rambo, Lee plans to make his own action-packed video epic.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisA Burlesque on Carmen (1915)
A gypsy seductress is sent to sway a goofy officer to allow a smuggling run.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies 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 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 thisCunk on Shakespeare (2016)
Fresh from her triumphs on Charlie Brooker's Weekly Wipe investigating time, Winston Churchill, and Donald Trump, Philomena Cunk has finally been given her own show - about William Shakespeare. Cunk will leave no stone unturned as she gets to the bottom of the Bard, visiting his birthplace, exploring the Globe, studying priceless artefacts and interviewing literally six different experts.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisThe Trouble with Angels (1966)
Mary and her friend, Rachel, are new students at St. Francis Academy, a boarding school run by the iron fist of Mother Superior. The immature teens grow bored and begin playing pranks on both the unsuspecting nuns and their unpleasant classmates, becoming a constant thorn in Mother Superior's side. However, as the years pass, Mary and Rachel slowly mature and begin to see the nuns in a different light.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies 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 thisShanghaied (1915)
A shipowner intends to scuttle his ship on its last voyage to get the insurance money. Charlie, a tramp in love with the owner's daughter, is grabbed by the captain and promises to help him shanghai some seamen. The daughter stows away to follow Charlie. Charlie assists in the galley and attempts to serve food during a gale.
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 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 thisClass Rank (2017)
Two high school misfits join forces in an attempt to overtake the local school board. Guided by their families, they enter the perilous word of politics and, in the process, learn a thing or two about love.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisSneakerella (2022)
When El, an aspiring sneaker designer from Queens, meets Kira King, the fiercely independent daughter of legendary basketball star and sneaker tycoon Darius King, sparks fly as the two bond over their mutual affinity for sneakers. With a little nudge from his best friend and a sprinkle of Fairy Godfather magic, El finds the courage to use his talent to pursue his dream of becoming a ‘legit’ sneaker designer in the industry.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisMr. Roosevelt (2017)
A young woman returns home and must confront her ex-boyfriend when an unexpected tragedy occurs.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisSextuplets (2019)
Father-to-be Alan is shocked to learn that he was born a sextuplet. With his newfound brother Russell riding shotgun, the duo sets out on a hilarious journey to reunite with their remaining long-lost siblings.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisAli Wong: Single Lady (2024)
After a whirlwind couple of years, Ali Wong returns to the stage to dish on the highs, lows and surprises of dating post-divorce.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisEddie Izzard: Dress to Kill (1999)
Eddie Izzard takes her show to San Francisco to give a brief history of pagan and Christian religions, the building of Stonehenge, the birth of the Church of England and of Western empires, and the need for a European dream.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisBeaned by a Beanshooter (1916)
Hero Handsome Harry must rescue his love interest, Lizzie, from a villainous character named Creampuff. Harry is repeatedly "beaned" by a beanshooter in the hands of a villainous boy and then Creampuff, but he overcomes the obstacles, defeats Creampuff, and ultimately is arrested for carrying a concealed weapon before being freed by the triumph of justice.
Why it matches: Similar story and style · both comedy
In Arcadia (1916)
The Youngloves have a cozy little apartment and a jewel of a cook, Bridget, and are happy until the landlord raises the rent. A slick agent convinces them to take a lease on "the modern Paradise” in Arcadia. A long, frightful journey takes them to "Eros Villa” a tumbledown old shack with a scrubby hedge running around it. After a veritable nightmare of a night trying to sleep on hastily-made-up hard beds and being scared nearly to death by huge rats scampering through the rooms the Youngloves rush to the agent's office, where he agrees to tear up the lease for two months' rent! The Youngloves, return to their old flat, sadder and wiser, but happy.
Why it matches: Similar story and style · both comedy
The Story of the Star Spangled Banner (1921)
A very rare lost film by Pathe Exchange that was found by Ben Model on eBay and preserved in time. Not much information known to exist.
Why it matches: Similar story and style · both comedy
A Son of Satan (1924)
A Son of Satan is a 1924 silent race film directed, written, produced and distributed by Oscar Micheaux. The film follows the misadventures of a man who accepted a bet to spend a night in a haunted house. Micheaux shot the film in The Bronx, New York, and Roanoke, Virginia. A Son of Satan ran into distribution problems when state censorship boards rejected the film based on its contents. New York censors objected to the film’s depiction of violence, particularly against women and animals (a cat is killed onscreen in one scene, a Ku Klux Klan leader is slain and a man chokes his wife to death), while Virginia censors complained the film’s references to miscegenation would "prove offensive to Southern ladies". In at least one state the film was banned for its title alone No print of the film is known to exist and it is presumed to be a lost film.
Why it matches: Similar story and style · both comedy
At the Sign of the Jack'O Lantern (1922)
When Harlan Carr inherited his Uncle Ebenezer's "Jack-O Lantern" house and too his bride there to live, he found himself the unwilling host of a score of hungry relatives within a week. Soon, strange things began to happen. A black cat made the house his headquarters, unexplained sounds could be heard and a shadowy figure floated through the halls at night.
Why it matches: Similar story and style · both comedy
The Revolt of Mr. Wiggs (1915)
Mr. Wiggs' wife is a militant suffragist, and he is the miserable sufferer left at home to mind their five children and feel that married life is closely approaching Sherman's idea of war. So, he decides to break her spirit with underhanded tricks. He succeeds but they are all poorer for his boorish behavior.
Why it matches: Similar story and style · both comedy
Are You a Mason? (1915)
Frank Perry's wife Helen is away visiting her mother, and he uses this "free time" for a night of drinking at a nightclub. Unfortunately, when he tries to return home, he enters the wrong house and is nearly arrested When Helen comes back he tells her that the "incident" was actually an initiation rite of the Masons, knowing that his wife has always wanted him to join the group. She excitedly tells her father about Frank's becoming a Mason, since her father is also a Mason. What neither she nor Frank know is that her father has actually been doing the same thing Frank is--pretending to be a Mason when he actually isn't. Complications ensue.
Why it matches: Similar story and style · both comedy
The Hired Man (1918)
Ezry is a hardworking hired man who saves his money carefully in the hopes one day of going to college. But when his girlfriend's brother gets in trouble for bank robbery, Ezry tries to help out by offering his savings in exchange for the stolen funds.
Why it matches: Similar story and style · both comedy
Sally Scrags, Housemaid (1913)
An author searches for inspiration for her novel by impersonating a housemaid.
Why it matches: Similar story and style · both comedy
We Moderns (1925)
Mary Sundale is a young woman who spurns her childhood sweetheart to attach herself to a large group of riotous, semi-artistic young people and becomes infatuated with a superficial poet and critic. One night this poet becomes too bold in his advances and is thrashed by the man who has been rejected. On a later night, the group holds a party in a dirigible. The ship crashes and fear grips the revelers. Mary, now disgusted with the group and all it represents, mends her manner of living and plans a future with the man who has always sincerely loved her. A lost film.
Why it matches: Similar story and style · both comedy
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Frequently asked questions
What are the best movies like The Gypsy Trail?
The closest matches to The Gypsy Trail are Driver's Ed (2026), Held Up (1999) and Why Worry? (1923). Below are 27 more, each with the reason it matches.
What should I watch after The Gypsy Trail?
Start with Driver's Ed (2026), the closest match to The Gypsy Trail.
What is the highest-rated movie like The Gypsy Trail?
Eddie Murphy Raw (1987), rated 7.2/10 by 394 TMDB users.
What is the newest movie like The Gypsy Trail?
Louis C.K.: Ridiculous (2026) is the most recent release on this list.
Are there English movies like The Gypsy Trail?
Yes: Driver's Ed (2026), Held Up (1999) and Why Worry? (1923).
How are movies similar to The Gypsy Trail chosen?
First come films that Trakt’s viewers watch alongside The Gypsy Trail, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.