Movies like A Crazy, Crazy 40-Year-Old Woman (2015)
The best movies like A Crazy, Crazy 40-Year-Old Woman (2015) are The Ladies Man (1961), The Trouble with Angels (1966) and Duplex (2003). If A Crazy, Crazy 40-Year-Old Woman hooked you with its comedy, these 20 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedLouis C.K.: Hilarious (2010)7.8/10 from 321 votes
- NewestSpa Weekend (2026)Released 2026
The Ladies Man (1961)
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 all these females?
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 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 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 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 thisLouis C.K.: Hilarious (2010)
In this unique and dynamic live concert experience, Louis C.K.'s exploration of life after 40 destroys politically correct images of modern life with thoughts we have all had...but would rarely admit to.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisSpa Weekend (2026)
Four lifelong friends realize that somewhere between careers, relationships, families, and everyday responsibilities, they’ve forgotten how to take care of themselves and each other. Burned out and overdue for a break, the women escape to a luxury spa retreat for an unforgettable weekend dedicated to fun, laughter, and a lot of really bad decisions.
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 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 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 thisThe Impostors (1998)
Wrongly accused of physically abusing a fellow actor, starving thespians Arthur and Maurice find themselves pursued by the law aboard a cruise ship.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe Errand Boy (1961)
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 ever finds is that he can cause havoc no matter what he does.
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 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 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 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 thisPete Davidson: Turbo Fonzarelli (2024)
Pete Davidson's fourth comedy special explores what it means to grow up, turning 30, love, life, and living in the woods.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisBabes (2024)
After getting pregnant from a one-night stand, a single woman leans on her married best friend and mother of two to guide her through gestation and beyond.
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 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 this
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Frequently asked questions
What are the best movies like A Crazy, Crazy 40-Year-Old Woman?
The closest matches to A Crazy, Crazy 40-Year-Old Woman are The Ladies Man (1961), The Trouble with Angels (1966) and Duplex (2003). Below are 17 more, each with the reason it matches.
What should I watch after A Crazy, Crazy 40-Year-Old Woman?
Start with The Ladies Man (1961), the closest match to A Crazy, Crazy 40-Year-Old Woman.
What is the highest-rated movie like A Crazy, Crazy 40-Year-Old Woman?
Louis C.K.: Hilarious (2010), rated 7.8/10 by 321 TMDB users.
What is the newest movie like A Crazy, Crazy 40-Year-Old Woman?
Spa Weekend (2026) is the most recent release on this list.
How are movies similar to A Crazy, Crazy 40-Year-Old Woman chosen?
First come films that Trakt’s viewers watch alongside A Crazy, Crazy 40-Year-Old Woman, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.