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Movies like How To Win

The best movies like How To Win are Homeward Bound: The Incredible Journey (1993), 21 & Over (2013) and Some Kind of Wonderful (1987). If How To Win hooked you, these 20 similar films are what to watch next, and every pick says why it matches.

Quick picks

  1. Homeward Bound: The Incredible Journey (1993)

    Before the Seavers leave for a family vacation to San Francisco, they drop off their pets -- Chance, an adventurous American bulldog; Shadow, a wise golden retriever; and Sassy, a cautious cat -- at a friend's ranch. But when the animals start to worry that they've been left for good, the three embark together on a treacherous and thrilling journey to find their way back home through the California wilderness.

    Why it matches: Recommended by TMDB viewers

    Worth the HypeMovies like this
  2. 21 & Over (2013)

    Brilliant student Jeff Chang has the most important interview of his life tomorrow. But today is still his birthday, what starts off as a casual celebration with friends evolves into a night of debauchery that risks to derail his life plan.

    Why it matches: Recommended by TMDB viewers

  3. Some Kind of Wonderful (1987)

    Keith Nelson, an artsy high school outcast, tries to land a date with popular girl Amanda Jones with some help from his tomboy best friend, Watts. However, Watts realizes she likes Keith as more than just a friend and tries to convince him to stop pursuing Amanda. Matters are further complicated when Keith's invitation draws the ire of Amanda's rich yet snobby ex-boyfriend, Hardy Jenns, who makes plans to get even.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  4. Seems Like Old Times (1980)

    After being falsely accused of robbing a bank, a writer seeks the help of his lawyer ex-wife to clear his name. However, hilarity ensues when he must hide from her husband, who’s throwing a party for law enforcement officials.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  5. Easy Living (1937)

    J.B. Ball, a rich financier, gets fed up with his free-spending family. He takes his wife's just-bought (very expensive) sable coat and throws it out the window, it lands on poor hard-working girl Mary Smith. But it isn't so easy to just give away something so valuable, as he soon learns.

    Why it matches: Recommended by TMDB viewers

    Worth the HypeMovies like this
  6. Incoming (2024)

    Their first week of high school. The biggest party of the year. Mistakes will be made as four teenage boys navigate a night of mayhem and debauchery.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  7. Spa 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

    Popcorn FlickMovies like this
  8. The Fox and the Hound (1981)

    When a feisty little fox named Tod is adopted into a farm family, he quickly becomes friends with a fun and adorable hound puppy named Copper. Life is full of hilarious adventures until Copper is expected to take on his role as a hunting dog -- and the object of his search is his best friend!

    Why it matches: Recommended by TMDB viewers

    Worth the HypeMovies like this
  9. Alice in Wonderland (1999)

    Alice follows a white rabbit down a rabbit-hole into a whimsical Wonderland, where she meets characters like the delightful Cheshire Cat, the clumsy White Knight, a rude caterpillar, and the hot-tempered Queen of Hearts and can grow ten feet tall or shrink to three inches. But will she ever be able to return home?

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  10. A Dogwalker's Christmas Tale (2015)

    Spoiled 21-year-old Luce Lockhart faces a tough decision when a handsome new friend asks her to help protect a dog park from her wealthy employer.

    Why it matches: Recommended by TMDB viewers

  11. Can't Buy Me Love (1987)

    Nerdy high schooler Ronald Miller rescues cheerleader Cindy Mancini from parental punishment after she accidentally destroys her mother's designer clothes. Ronald agrees to pay for the $1,000 outfit on one condition: that she will act as though they're a couple for an entire month. As the days pass, however, Cindy grows fond of Ronald, making him popular. But when Ronald's former best friend gets left behind, he realizes that social success isn't everything.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  12. Puppy Love (2023)

    After a disastrous first date, wild-child Nicole and socially-anxious Max vow to lose each other’s numbers until they learn that their dogs found a love match, and now puppies are on the way! The hilariously mismatched Nicole and Max are forced to become responsible co-parents, but may end up finding love themselves.

    Why it matches: Recommended by TMDB viewers

    Worth the HypeMovies like this
  13. Dear Wendy (2005)

    In a blue-collar American town, a group of teens bands together to form the Dandies, a gang of gunslingers led by Dick Dandelion. Following a code of strict pacifism at odds with the fact that they all carry guns, the group eventually lets in Sebastian, the grandson of Dick's childhood nanny, Clarabelle, who fears the other gangs in the area. Dick and company try to protect Clarabelle, but events transpire that push the gang past posturing.

    Why it matches: Recommended by TMDB viewers

  14. Trading Places (1983)

    A snobbish investor and a wily street con-artist find their positions reversed as part of a bet by two callous millionaires.

    Why it matches: Recommended by TMDB viewers

    Worth the HypeMovies like this
  15. House Party (1990)

    Young Kid has been invited to a party at his friend Play's house. But after a fight at school, Kid's father grounds him. None the less, Kid sneaks out when his father falls asleep. But Kid doesn't know that three of the thugs at school have decided to give him a lesson in behavior.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  16. Long Weekend (2021)

    Bart's chance encounter with the enigmatic Vienna leads to a whirlwind weekend together. The two fall fast and hard, but both carry secrets that could be their undoing or the chance for a fresh start.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  17. Gloria Bell (2019)

    Gloria is a free-spirited divorcée who spends her days at a straight-laced office job and her nights on the dance floor, joyfully letting loose at clubs around Los Angeles. After meeting Arnold on a night out, she finds herself thrust into an unexpected new romance, filled with both the joys of budding love and the complications of dating, identity, and family.

    Why it matches: Recommended by TMDB viewers

  18. Man's Favorite Sport? (1964)

    Roger Willoughby is a renowned fishing expert, who, unbeknownst to his friends, co-workers, or boss, has never cast a line in his life. One day, he crosses paths with Abigail Paige, a sweetly annoying girl who has just badgered his boss into signing Roger up for an annual fishing tournament.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this
  19. Duplex (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

    Popcorn FlickMovies like this
  20. Grown Ups 2 (2013)

    Lenny has relocated his family back to the small town where he and his friends grew up. This time around, the grown ups are the ones learning lessons from their kids on a day notoriously full of surprises—the last day of school.

    Why it matches: Recommended by TMDB viewers

    Popcorn FlickMovies like this

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Frequently asked questions

What are the best movies like How To Win?

The closest matches to How To Win are Homeward Bound: The Incredible Journey (1993), 21 & Over (2013) and Some Kind of Wonderful (1987). Below are 17 more, each with the reason it matches.

What should I watch after How To Win?

Start with Homeward Bound: The Incredible Journey (1993), the closest match to How To Win.

What is the highest-rated movie like How To Win?

The Fox and the Hound (1981), rated 7.2/10 by 3,631 TMDB users.

What is the newest movie like How To Win?

Spa Weekend (2026) is the most recent release on this list.

Are there English movies like How To Win?

Yes: Homeward Bound: The Incredible Journey (1993), 21 & Over (2013) and Some Kind of Wonderful (1987).

How are movies similar to How To Win chosen?

First come films that Trakt’s viewers watch alongside How To Win, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.

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