Movies Like The Skipper Surprised His Wife

If you liked The Skipper Surprised His Wife (1950), a comedy movie directed by Elliott Nugent, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
The Ladies Man (1961)
★ 6.3/10Also comedy
After his girl leaves him for someone else, Herbert gets really depressed and starts searching for a job. He finally finds one in a big house which is inhabited by many, many women. Can he live in the same home with…
2
Cadet Kelly (2002)
★ 6.2/10Also comedy
Hyperactive teenager Kelly is enrolled into a military school when her new stepfather becomes the Commandant. At first she has problems fitting in and taking orders until she tries out for the drill team.
3
Playing with Fire (2019)
★ 6.6/10Also comedy
A crew of rugged firefighters meet their match when attempting to rescue three rambunctious kids.
4
The Errand Boy (1961)
★ 6.2/10Also comedy
Paramutual Pictures wants to know where all the money is going so they hire Morty to be their spy. Morty works for Mr. Sneak and gets a job in the mail room so that he can have access to the lot. But all that Morty…
5
The Trouble with Angels (1966)
★ 6.7/10Also comedy
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…
6
Johnny English Strikes Again (2018)
★ 6.3/10Also comedy
Disaster strikes when a criminal mastermind reveals the identities of all active undercover agents in Britain. The secret service can now rely on only one man - Johnny English. Currently teaching at a minor prep…
7
The Wackiest Ship in the Army (1960)
★ 6.1/10Also comedy
Lieutenant Rip Crandall is hoodwinked into taking command of the "Wackiest Ship in the Navy" – a real garbage scow with a crew of misfits who don't know a jib from a jigger. What none of them knows, including Crandall…
8
Beverly Hills Chihuahua 2 (2011)
★ 5.9/10Also comedy
Puppy mayhem turns the lives of newlywed Chihuahua parents Papi and Chloe upside down when their rambunctious, mischievous puppies present one challenge after another. But when their human owners end up in trouble, the…
9
Who's Minding the Store? (1963)
★ 6.8/10Also comedy
Norman Phiffer, a proud man in a humble life, doesn't know that his girlfriend, Barbara, is heir to the Tuttle Department Store dynasty. Mrs. Tuttle, Barbara's mother, is determined to split the two lovers, and hires…
10
The Air Up There (1994)
★ 6.1/10Also comedy
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…
11
Much Ado About Nothing (2013)
★ 6.8/10Also comedy
A modern retelling of Shakespeare's classic comedy about two pairs of lovers with different takes on romance and a way with words.
12
Rookie of the Year (1993)
★ 6.2/10Also comedy
When the cast comes off his once broken arm, a 12-year-old boy can throw a 100-mile-an-hour fastball, and the Chicago Cubs want him as their new pitcher.
13
Adventures in Public School (2018)
★ 6.3/10Also comedy
A socially-awkward, home-schooled kid forces his way into public school against his suffocating, but loving, mother's wishes.
14
Jim Jefferies: Freedumb (2016)
★ 7.2/10Also comedy
Returning for a second Netflix comedy special, Jim Jefferies unleashes his famously ferocious black humor to a packed house in Nashville, Tennessee.
15
Stewie Griffin: The Untold Story (2005)
★ 6.9/10Also comedy
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.
16
American Dreamer (2022)
★ 6/10Also comedy
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.
17
Animal Crackers (1930)
★ 6.9/10Also comedy
The well-known explorer and hunter Captain Spaulding has just returned from Africa, and is being welcomed home with a lavish party at the estate of influential society matron Mrs. Rittenhouse when a valuable painting…
18
A Burlesque on Carmen (1915)
★ 5.8/10Also comedy
A gypsy seductress is sent to sway a goofy officer to allow a smuggling run.
19
Airplane II: The Sequel (1982)
★ 6.1/10Also comedy
A faulty computer causes a passenger space shuttle to head straight for the sun, and man-with-a-past Ted Striker must save the day and get the shuttle back on track – again – all the while trying to patch up his…
20
Dennis the Menace (1993)
★ 5.9/10Also comedy
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…