Movies like The Skipper's Wooing (1922)
The best movies like The Skipper's Wooing (1922) are I Love My Dad (2022), Adventures in Public School (2018) and Mr. Bones (2001). If The Skipper's Wooing 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
- NewestDriver's Ed (2026)Released 2026
I 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 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 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 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 thisFist Fight (2017)
When one school teacher gets the other fired, he is challenged to an after-school fight.
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 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 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 thisPsycho Therapy: The Shallow Tale of a Writer Who Decided to Write About a Serial Killer (2025)
A struggling writer in the midst of a divorce befriends a retired serial killer who incidentally becomes his marriage counselor by day, and killing counselor for his next book by night.
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 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 thisPretty Persuasion (2005)
A 15-year-old girl incites chaos among her friends and a media frenzy when she accuses her drama teacher of sexual harassment.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisDie, Mommie, Die! (2003)
Angela Arden is a washed up, has-been singing star who is trapped in a hateful marriage to film producer Sol Sussman. In an attempt to escape her marriage so that she can be with a hunky layabout, she poisons her husband. However, Angela's manipulative daughter, gay son and alcoholic maid are not going to make it easy for her.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe Anniversary (1968)
Mrs Taggart always celebrates her anniversary with her grown sons. It’s a tradition practised since the death of her husband and she is determined for it to continue. None of her three sons have dared to cross their ruthless domineering mother but this anniversary they intend to try. With cruel and brutal twists, the family get-together becomes a social nightmare beyond endurance.
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 thisThe Happiest Days of Your Life (1950)
Nutbourne College, an old established, all-boys, boarding school is told that another school is to be billeted with due to wartime restrictions. The shock is that it's an all-girls school that has been sent. The two head teachers are soon battling for the upper hand with each other and the Ministry. But a crisis (or two) forces them to work together.
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 thisAnuvahood (2011)
Kenneth (who likes to call himself Kay) begins to realise he's just another wannabe bad boy... even less than a loser in fact. After quitting his job at Laimsbury's, Kay vows to become a respected gangster... or cry trying. A pulls-no-punches, coming-of-age story, centering on one directionless hopeless "shotter", who finds his true worth in the face of urban adversity.
Why it matches: Recommended by TMDB viewers · both comedy
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Frequently asked questions
What are the best movies like The Skipper's Wooing?
The closest matches to The Skipper's Wooing are I Love My Dad (2022), Adventures in Public School (2018) and Mr. Bones (2001). Below are 17 more, each with the reason it matches.
What should I watch after The Skipper's Wooing?
Start with I Love My Dad (2022), the closest match to The Skipper's Wooing.
What is the highest-rated movie like The Skipper's Wooing?
Much Ado About Nothing (2013), rated 6.8/10 by 299 TMDB users.
What is the newest movie like The Skipper's Wooing?
Driver's Ed (2026) is the most recent release on this list.
Are there English movies like The Skipper's Wooing?
Yes: I Love My Dad (2022), Adventures in Public School (2018) and Mr. Bones (2001).
How are movies similar to The Skipper's Wooing chosen?
First come films that Trakt’s viewers watch alongside The Skipper's Wooing, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.