Movies like Tender But Cheeky Like Oskar (1980)
The best movies like Tender But Cheeky Like Oskar (1980) are People We Meet on Vacation (2026), In July (2000) and National Lampoon's Vacation (1983). If Tender But Cheeky Like Oskar hooked you, these 20 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedIndiana Jones and the Last Crusade (1989)7.9/10 from 11,536 votes
- NewestExtreme Makeover: Homer Edition (2026)Released 2026
- In GermanIn July (2000)Also in German
People We Meet on Vacation (2026)
Poppy's a free spirit. Alex loves a plan. After years of summer vacations, these polar-opposite pals wonder if they could be a perfect romantic match.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisIn July (2000)
Daniel’s drab existence as a physics teacher takes an adventurous turn when he falls in love with a Turkish girl named Melek. He spontaneously decides to follow her to Instanbul by car. On the road across Europe, he picks up his free-spirited friend Juli, who is secretly in love with him.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisNational Lampoon's Vacation (1983)
Clark Griswold is on a quest to take his family to the Walley World theme park for a vacation, but things don't go exactly as planned.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisDumb and Dumber (1994)
Lloyd and Harry are two men whose stupidity is really indescribable. When Mary, a beautiful woman, loses an important suitcase with money before she leaves for Aspen, the two friends (who have found the suitcase) decide to return it to her. After some "adventures" they finally get to Aspen where, using the lost money they live it up and fight for Mary's heart.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisThe Great Outdoors (1988)
It's vacation time for outdoorsy Chicago man Chet Ripley, along with his wife, Connie, and their two kids, Buck and Ben. But a serene weekend of fishing at a Wisconsin lakeside cabin gets crashed by Connie's obnoxious brother-in-law, Roman Craig, his wife, Kate, and the couple's two daughters. As the excursion wears on, the Ripleys find themselves at odds with the stuffy Craig family.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisShag (1989)
Summer of 1963. Carson is getting married to her boyfriend so her friends Melaina, Pudge and Luanne take her to Myrtle Beach for one last irresponsible weekend.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisWild Hogs (2007)
Restless and ready for an adventure, four suburban bikers leave the safety of their subdivision and head out on the open road. But complications ensue when they cross paths with an intimidating band of New Mexico bikers known as the Del Fuegos.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisHunt for the Wilderpeople (2016)
Ricky is a defiant young city kid who finds himself on the run with his cantankerous foster uncle in the wild New Zealand bush. A national manhunt ensues, and the two are forced to put aside their differences and work together to survive.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies 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
Popcorn FlickMovies like thisIndiana Jones and the Last Crusade (1989)
In 1938, an art collector appeals to eminent archaeologist Dr. Indiana Jones to embark on a search for the Holy Grail. Indy learns that a medieval historian has vanished while searching for it, and the missing man is his own father, Dr. Henry Jones Sr.. He sets out to rescue his father by following clues in the old man's notebook, which his father had mailed to him before he went missing. Indy arrives in Venice, where he enlists the help of a beautiful academic, Dr. Elsa Schneider, along with Marcus Brody and Sallah. Together they must stop the Nazis from recovering the power of eternal life and taking over the world!
Why it matches: Recommended by TMDB viewers
Absolute CinemaMovies like thisDisaster Holiday (2024)
A workaholic dad, trying to win over his kids, heads to the coast of Durban for a big work meeting — under the guise of a family road trip vacation.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisStand by Me (1986)
After learning that a boy their age has been accidentally killed near their rural homes, four boys decide to go see the body. Gordie, Vern, Chris, and Teddy encounter a mean junk man and a marsh full of leeches, but they also learn more about one another and their very different home lives. Just a lark at first, the boys' adventure evolves into a defining event in their lives.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisBonjour Tristesse (2025)
At the height of summer, 18-year-old Cécile is relaxing by the French seaside with her father and falling in love with her new boyfriend. The arrival of her late mother's enigmatic friend turns her world upside down.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisWeekend at Bernie's (1989)
Two young insurance corporation employees try to pretend that their murdered employer is alive by puppeteering his dead body, leading a hitman to attempt to track him down to finish him off.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisCocoon (2020)
In the heat of a shimmering Berlin summer, Nora spends her days as a third wheel to her older sister Jule and her best friend Aylin. When Romy comes onto the scene, a friendship blossoms. Nora instantly falls for her, opening up a whole new world and unexpected summer of love.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisAvanti! (1972)
A successful businessman travels to Italy to arrange for the return of his tycoon father's body, only to learn that dear old dad died with his longtime mistress.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisExtreme Makeover: Homer Edition (2026)
Homer and Marge's fun couples' date night goes off the rails when Marge learns Homer left the kids unsupervised with only the doorbell camera as a babysitter. Frustrated with her imperfect husband, a tipsy Marge stirs up a trilogy of fantasies of a different Homer.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisRiddle of Fire (2024)
Three mischievous children embark on a woodland odyssey when their mother sends them on an errand.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisInstant Family (2018)
When Pete and Ellie decide to start a family, they stumble into the world of foster care adoption. They hope to take in one small child but when they meet three siblings, including a rebellious 15 year old girl, they find themselves speeding from zero to three kids overnight.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisThink Like a Man Too (2014)
All the couples are back for a wedding in Las Vegas, but plans for a romantic weekend go awry when their various misadventures get them into some compromising situations that threaten to derail the big event.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like this
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Frequently asked questions
What are the best movies like Tender But Cheeky Like Oskar?
The closest matches to Tender But Cheeky Like Oskar are People We Meet on Vacation (2026), In July (2000) and National Lampoon's Vacation (1983). Below are 17 more, each with the reason it matches.
What should I watch after Tender But Cheeky Like Oskar?
Start with People We Meet on Vacation (2026), the closest match to Tender But Cheeky Like Oskar.
What is the highest-rated movie like Tender But Cheeky Like Oskar?
Indiana Jones and the Last Crusade (1989), rated 7.9/10 by 11,536 TMDB users.
What is the newest movie like Tender But Cheeky Like Oskar?
Extreme Makeover: Homer Edition (2026) is the most recent release on this list.
Are there German movies like Tender But Cheeky Like Oskar?
Yes: In July (2000) and Cocoon (2020).
How are movies similar to Tender But Cheeky Like Oskar chosen?
First come films that Trakt’s viewers watch alongside Tender But Cheeky Like Oskar, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.