Movies like How to Take a Vacation (1941)
The best movies like How to Take a Vacation (1941) are Me Time (2022), Held Up (1999) and Tommy Boy (1995). If How to Take a Vacation hooked you with its comedy, these 20 similar films are what to watch next, and every pick says why it matches.
How to Take a Vacation
Quick picks
- Highest ratedRicky Gervais: Humanity (2018)7.6/10 from 547 votes
- NewestLouis C.K.: Ridiculous (2026)Released 2026
Me Time (2022)
With his family away, a devoted stay-at-home dad enjoys his first me time in years by joining his hard-partying old friend on a wild birthday adventure.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies 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 thisTommy Boy (1995)
To save the family business, two ne’er-do-well traveling salesmen hit the road with disastrously funny consequences.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisGood Neighbor Sam (1964)
To help his divorced neighbor claim a substantial inheritance, a family man poses as her husband. The ruse spills over into his career in advertising, and his recent promotion relies on his wholesome and moral appearance.
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 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 thisRicky Gervais: Humanity (2018)
In his first special in seven years, Ricky Gervais slings his trademark snark at celebrity, mortality and a society that takes everything personally.
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 thisDave Chappelle: The Closer (2021)
As he closes out his slate of comedy specials, Dave takes the stage to try and set the record straight — and get a few things off his chest.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisJudy Moody and the Not Bummer Summer (2011)
Third-grader Judy Moody sets out to have the most thrilling summer of her life.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisThe Roast of Tom Brady (2024)
Offensive lines. Full-contact comedy. Kevin Hart hosts this all-star roast of NFL legend Tom Brady.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisChris Rock: Never Scared (2004)
Chris Rock, the three-time Emmy Award-winner, comedian, actor, and host of HBO's acclaimed The Chris Show, stars in his fourth solo stand-up special for HBO, Chris Rock: Never Scared. Featuring his unique, insightful, and hilarious views on a host of social, political and, celebrity issues, Rock confirms his stature as the leading comic of our time.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies 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 thisAli Wong: Single Lady (2024)
After a whirlwind couple of years, Ali Wong returns to the stage to dish on the highs, lows and surprises of dating post-divorce.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisRicky Gervais: Mortality (2025)
Ricky Gervais tackles life, death and the state of the world in a brutally honest special that spares no topic, even his own mortality.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe Breadwinner (2026)
After his wife Katie lands a once-in-a-lifetime deal on Shark Tank that takes her on a prolonged business trip - lifelong breadwinner Nate Wilcox now has to fend for his family as a first-time stay-at-home dad.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisBarb & Star Go to Vista Del Mar (2021)
The story of best friends Barb and Star, who leave their small midwestern town for the first time to go on vacation in Vista Del Mar, Florida, where they soon find themselves tangled up in adventure, love, and a villain’s evil plot to kill everyone in town.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisChief Daddy 2: Going for Broke (2021)
The Beecroft family are ready to spend all of Chief Daddy's inheritance, but not if the CEO of his company has anything to do with it.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisSummer Rental (1985)
Jack Chester, an overworked air traffic controller, takes his family on vacation to the beach. Things immediately start to go wrong for the Chesters, and steadily get worse. Jack ends up in a feud with a local yachtsman, and has to race him to regain his pride and family's respect.
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 this
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Frequently asked questions
What are the best movies like How to Take a Vacation?
The closest matches to How to Take a Vacation are Me Time (2022), Held Up (1999) and Tommy Boy (1995). Below are 17 more, each with the reason it matches.
What should I watch after How to Take a Vacation?
Start with Me Time (2022), the closest match to How to Take a Vacation.
What is the highest-rated movie like How to Take a Vacation?
Ricky Gervais: Humanity (2018), rated 7.6/10 by 547 TMDB users.
What is the newest movie like How to Take a Vacation?
Louis C.K.: Ridiculous (2026) is the most recent release on this list.
Are there English movies like How to Take a Vacation?
Yes: Me Time (2022), Held Up (1999) and Tommy Boy (1995).
How are movies similar to How to Take a Vacation chosen?
First come films that Trakt’s viewers watch alongside How to Take a Vacation, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.