Movies like Crimson Sails (2001)
The best movies like Crimson Sails (2001) are Class Rank (2017), The Air Up There (1994) and After the Ball (2015). If Crimson Sails hooked you with its comedy, these 20 similar films are what to watch next, and every pick says why it matches.
Crimson Sails
Quick picks
- Highest ratedChickenhare and the Hamster of Darkness (2022)7.2/10 from 299 votes
- NewestSimpsley (2026)Released 2026
Class 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 thisThe Air Up There (1994)
Jimmy Dolan is a college basketball coach who wants a big promotion. To get it, he needs to make a dramatic find. He ends up deep in Africa, hoping to recruit Saleh, a huge basketball prodigy Jimmy glimpsed in a home movie. But Saleh is the chief's son and has responsibilities at home, since the tribe's land is threatened by a mining company with its own hotshot basketball team.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies 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 thisDuplex (2003)
When a young couple buys their dream home, they have no idea what the sweet little old lady upstairs is going to put them through!
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 thisThunderstruck (2012)
After NBA star Kevin Durant switches talent with 16 year old Brian, the teenager becomes the star of his high school team, but Durant starts struggling and eventually learns an important lesson.
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
Worth the HypeMovies like thisSketch (2025)
When a young girl’s sketchbook falls into a strange pond, her drawings come to life—chaotic, real, and on the loose. As the town descends into chaos, her family must reunite and stop the monsters they never meant to unleash.
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 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 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 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 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 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 thisChickenhare and the Hamster of Darkness (2022)
A brave young animal explorer teams up with two trusty friends to find a powerful artifact before his greedy uncle can get his paws on it.
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 thisSlumberland (2022)
A young girl discovers a secret map to the dreamworld of Slumberland, and with the help of an eccentric outlaw, she traverses dreams and flees nightmares, with the hope that she will be able to see her late father again.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisThe Fixer Uppers (1935)
Stan and Ollie are greeting card salesmen who agree to help a woman put a spark in her loveless marriage by making her husband jealous.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisSimpsley (2026)
When penniless con-artist Marge Bouvier is sent to Italy to convince wealthy sap Seymour Skinner to come home, she's tempted by the trappings of his affluent lifestyle. But there’s a big fat fly in the ointment: Skinner's clingy, dim-witted mooch of a houseguest, Homer Simpsley. Lies, lust and Italian lira are abound.
Why it matches: Recommended by TMDB viewers · both comedy
Absolute CinemaMovies like thisMy Sweet Little Village (1985)
The movie's main storyline follows the life of Otík, a young man, in a tight-knit village community. The sweet-tempered Otík works as an assistant truck driver with Mr. Pávek, his older colleague and practical-minded neighbor. Pávek's family takes care of Otík, whose parents are dead. However, the two coworkers become at odds over Otík's inability to perform even the simplest tasks. Pávek demands that Otík be transferred to assist another driver, who happens to be a choleric and suspicious man named Turek (Turk in Czech). Rather than work with Turek, Otík decides to accept an offer of employment in Prague, but finds he does not fit in to the city life. After discovering that the transfer of Otík to Prague was a trick by a crooked politician to get a deal on Otík's large inherited house, Pávek agrees to give Otík a second chance and retrieves him from the city to resume their work together.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like this
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Frequently asked questions
What are the best movies like Crimson Sails?
The closest matches to Crimson Sails are Class Rank (2017), The Air Up There (1994) and After the Ball (2015). Below are 17 more, each with the reason it matches.
What should I watch after Crimson Sails?
Start with Class Rank (2017), the closest match to Crimson Sails.
What is the highest-rated movie like Crimson Sails?
Chickenhare and the Hamster of Darkness (2022), rated 7.2/10 by 299 TMDB users.
What is the newest movie like Crimson Sails?
Simpsley (2026) is the most recent release on this list.
How are movies similar to Crimson Sails chosen?
First come films that Trakt’s viewers watch alongside Crimson Sails, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.