Movies like The Skipper's Flirtation (1921)
The best movies like The Skipper's Flirtation (1921) are Fun with Dick and Jane (1977), Louis C.K.: Ridiculous (2026) and One Night at McCool's (2001). If The Skipper's Flirtation hooked you with its comedy, these 20 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedChickenhare and the Hamster of Darkness (2022)7.2/10 from 299 votes
- NewestLouis C.K.: Ridiculous (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 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 thisOne Night at McCool's (2001)
On an ordinary night, in an ordinary part of town, a beautiful young woman walks into a bar. Her name is Jewel, and before long she is chatting to bartender Randy. The pair leave together, but he ends up getting into a tussle with her criminal boyfriend, who she then shoots dead, later persuading Randy to take the rap for her. But this isn't the end of it, as both Randy's cousin Carl and the detective assigned to the murder case also fall for Jewel's charms and find themselves caught up in the ensuing events. It seems that any man who meets Jewel falls instantly in love with her, and she's going to use this fully to her own advantage, leaving a trail of havoc in her wake. It also seems that she is going to get away with it - that is, until Randy decides to hire a hitman...
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisJackass Presents: Bad Grandpa (2013)
86-year-old Irving Zisman is on a journey across America with the most unlikely companion: his 8 year-old grandson, Billy.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisTake the Money and Run (1969)
Virgil Starkwell is intent on becoming a notorious bank robber. Unfortunately for Virgil and his not-so-budding career, he is completely incompetent.
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 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 thisHard to Die (1990)
While doing the inventory for a lingerie outlet in a high rise office building, five attractive women are terrorized by a series of bizarre killings. They suspect that the strange janitor, who witnessed another series of killings six months previously, is at the bottom of the whole thing. Little do they know the real horror that they face in the end.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisStewie Griffin: The Untold Story (2005)
The maniacal baby of the Griffin family, Stewie, meets his future self. In doing this he discovers that his future image is not what he has anticipated because of a near death experience.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisHappiness Is a Warm Blanket, Charlie Brown (2011)
Linus is pushed to his limits when he learns Grandma is coming to visit and plans on ridding him of his childish security blanket.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies 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 thisDennis the Menace (1993)
Mr. Wilson's ever-present annoyance comes in the form of one mischievous kid named Dennis. But he'll need Dennis's tricks to uncover a collection of gold coins that go missing when a shady drifter named Switchblade Sam comes to town.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisA Loud House Christmas (2021)
Lincoln Loud gears up for the ultimate Christmas, until he finds out that most of his sisters have plans to be elsewhere for the big day. Determined to remind his family that they all need to be together, Lincoln and his best friend Clyde McBride embark on a mission to preserve the family’s holiday traditions.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisPerfect Day (1929)
Two families embark on a pleasant Sunday picnic but manage to run into a variety of issues with their temperamental automobile. Each incident requires repeated exits and reboardings by Laurel, Hardy, their wives and grouchy, gout-ridden Uncle Edgar.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisLaRoy, Texas (2024)
Broke and depressed, Ray is mistaken for a dangerous hitman and given an envelope of cash. Along with his P.I. friend Skip, he must escape the actual hitman to make it out of LaRoy alive.
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 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 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 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 thisA-Haunting We Will Go (1942)
Stan and Ollie get involved with con men, crooks, a genial magician, and two interchangeable coffins with disastrous but funny results.
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 The Skipper's Flirtation?
The closest matches to The Skipper's Flirtation are Fun with Dick and Jane (1977), Louis C.K.: Ridiculous (2026) and One Night at McCool's (2001). Below are 17 more, each with the reason it matches.
What should I watch after The Skipper's Flirtation?
Start with Fun with Dick and Jane (1977), the closest match to The Skipper's Flirtation.
What is the highest-rated movie like The Skipper's Flirtation?
Chickenhare and the Hamster of Darkness (2022), rated 7.2/10 by 299 TMDB users.
What is the newest movie like The Skipper's Flirtation?
Louis C.K.: Ridiculous (2026) is the most recent release on this list.
Are there English movies like The Skipper's Flirtation?
Yes: Fun with Dick and Jane (1977), Louis C.K.: Ridiculous (2026) and One Night at McCool's (2001).
How are movies similar to The Skipper's Flirtation chosen?
First come films that Trakt’s viewers watch alongside The Skipper's Flirtation, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.