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Movies like Winners and Losers (2005)

The best movies like Winners and Losers (2005) are Yoh! Bestie (2026), The Prince & Me 4: The Elephant Adventure (2010) and What's Love Got to Do with It? (2023). If Winners and Losers hooked you with its romance and comedy, these 30 similar films are what to watch next, and every pick says why it matches.

Quick picks

  1. Yoh! Bestie (2026)

    Thando is perpetually unlucky in love, but when her bestie returns from his travels with a fiancée in tow, she's forced to face a new emotion — jealousy.

    Why it matches: Recommended by TMDB viewers · both romance & comedy

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  2. The Prince & Me 4: The Elephant Adventure (2010)

    One year after their royal wedding, King Edvard and Queen Paige of Denmark receive an invitation to attend the wedding of Princess Myra of Sangyoon. Upon their arrival, Paige finds Myra is unhappy with her arranged marriage to the brooding and sinister Kah and is secretly in love with a young elephant handler named Alu.

    Why it matches: Recommended by TMDB viewers · both comedy & romance

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  3. What's Love Got to Do with It? (2023)

    Two childhood friends now in their thirties must decide whether to follow their heads or their hearts once the man decides to follow his parents' advice and enter into an arranged marriage in Pakistan.

    Why it matches: Recommended by TMDB viewers · both romance & comedy

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  4. Boot Camp (2024)

    Unathletic Whitney Carmichael signs up for an intense summer boot camp to reinvent herself and falls for her personal trainer. She then finds the strength to embrace her true self and ignore the others' expectations.

    Why it matches: Recommended by TMDB viewers · both romance & comedy

    Popcorn FlickMovies like this
  5. Love, Weddings & Other Disasters (2020)

    A fussy celebrity caterer, a blind woman, a tour-bus guide and an inexperienced wedding planner search for love.

    Why it matches: Recommended by TMDB viewers · both romance & comedy

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  6. This Little Love of Mine (2021)

    Laura Price is a successful San Francisco lawyer on the cusp of promotion – a far cry from her childhood growing up on a tropical island with best friends Chip and Gem. When the firm’s biggest client – Chip’s grandfather – asks Laura to travel to the island and deliver a contract to make Chip his heir, she leaves behind her practice and fiancé Owen to convince her childhood friend to sign a contract that will make him a billionaire.

    Why it matches: Recommended by TMDB viewers · both romance & comedy

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  7. Love Is in the Air (2023)

    A fiercely independent pilot fighting to keep her family business afloat starts to fall for the man sent by corporate to ground her operation forever.

    Why it matches: Recommended by TMDB viewers · both romance & comedy

    Popcorn FlickMovies like this
  8. Wedding Season (2022)

    Pressured by their immigrant parents to find spouses, two Indian-Americans pretend to date in order to survive a summer of weddings – but find themselves falling for each other as they struggle to balance who they are with who their parents want them to be.

    Why it matches: Recommended by TMDB viewers · both romance & comedy

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  9. Love Jacked (2018)

    Maya, a headstrong 28-year-old with artistic ambitions – a strong contrast to what her father Ed wants: a dutiful daughter to run the family store. Ed is shocked when Maya takes her assertions of independence a step further and decides to travel to Africa for inspiration and returns with a fiancé who is not quite what he seems.

    Why it matches: Recommended by TMDB viewers · both romance & comedy

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  10. Return to Me (2000)

    It took a lot of persuading to get Bob, a recently widowed architect, to go on a blind date at a quirky Irish-Italian eatery. Once there, he’s instantly smitten, not with his date, but with the sharp-witted waitress. Everything seems to be going great until an unbelievable truth is revealed, one that could easily break both of their hearts for good.

    Why it matches: Recommended by TMDB viewers · both romance & comedy

    Popcorn FlickMovies like this
  11. Relationship Goals (2026)

    When TV producer Leah Caldwell aims to become the first woman running New York's top morning show, her ex competes for the same role. Leah stays focused on her career, until chemistry with her ex challenges her priorities.

    Why it matches: Recommended by TMDB viewers · both romance & comedy

    Popcorn FlickMovies like this
  12. Chasing Papi (2003)

    Playboy Thomas Fuentes has so far been able to skate by in life on good looks and charm alone. But when his duplicitous relationships with three women -- impassioned waitress Cici, meticulous lawyer Lorena and bored socialite Patricia -- spiral out of control, he suffers a mental breakdown. His doctor recommends that he choose just one girlfriend -- but can he choose in time before they discover his deception?

    Why it matches: Recommended by TMDB viewers · both comedy & romance

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  13. The Wrong Paris (2025)

    Dawn thinks she's joining a dating show in Paris, France, only to land in Paris, Texas. She has an exit plan — until sparks fly with the cowboy bachelor.

    Why it matches: Recommended by TMDB viewers · both romance & comedy

    Popcorn FlickMovies like this
  14. Run Fatboy Run (2007)

    Five years after jilting his pregnant fiancée on their wedding day, out-of-shape Dennis decides to run a marathon to win her back.

    Why it matches: Recommended by TMDB viewers · both comedy & romance

    Popcorn FlickMovies like this
  15. The Royal Treatment (2022)

    Isabella runs her own salon and isn’t afraid to speak her mind, while Prince Thomas runs his own country and is about to marry for duty rather than love. When Izzy and her fellow stylists get the opportunity of a lifetime to do the hair for the royal wedding, she and Prince Thomas learn that taking control of their own destiny requires following their hearts.

    Why it matches: Recommended by TMDB viewers · both romance & comedy

    Popcorn FlickMovies like this
  16. Good Advice (2001)

    An investment banker loses everything and must discover what's really important in life.

    Why it matches: Recommended by TMDB viewers · both comedy & romance

  17. Only the Lonely (1991)

    Danny Muldoon, a Chicago policeman, still lives with his overbearing mother Rose. He meets and falls in love with Theresa Luna, whose father owns the local funeral parlour. Naturally, his mother objects to the relationship, and Danny and Theresa must either overcome her objections or give up the romance.

    Why it matches: Recommended by TMDB viewers · both comedy & romance

    Popcorn FlickMovies like this
  18. Racing Stripes (2005)

    Shattered illusions are hard to repair -- especially for a good-hearted zebra named Stripes who's spent his life on a Kentucky farm amidst the sorely mistaken notion that he's a debonair thoroughbred. Once he faces the fact that his stark stripes mark him as different, he decides he'll race anyway. And with help from the young girl who raised him, he just might end up in the winner's circle.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  19. New Mischief by Emil (1972)

    Emil's reputation for being a troublemaker makes the Svensson family's neighbours take up a collection for sending the boy off to America. But even if he among other unfortunate mishaps causes his father to get stuck in the outhouse window and get bitten by crawfish, all is forgotten when he skillfully wins the family a free horse. And when Alfred the farmhand gets seriously ill, Emil puts his own life on the line, venturing into a snow storm to get his best friend to a doctor before it is too late.

    Why it matches: Recommended by TMDB viewers · both comedy

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  20. My Little Pony: A New Generation (2021)

    Equestria's divided. But a bright-eyed hero believes Earth Ponies, Pegasi and Unicorns should be pals — and, hoof to heart, she’s determined to prove it.

    Why it matches: Recommended by TMDB viewers · both comedy

    Worth the HypeMovies like this
  21. Sabrina (1995)

    After her return from school in Paris, a playboy finally takes notice of his family's chauffeur's daughter Sabrina, who's long had a crush on him, but he questions his more serious brother's motives when he warns against getting involved with her.

    Why it matches: Similar story and style · both romance & comedy

    Popcorn FlickMovies like this
  22. The Party (1980)

    A thirteen-year-old French girl deals with moving to a new city and school in Paris, while at the same time her parents are getting a divorce.

    Why it matches: Similar story and style · both romance & comedy

    Popcorn FlickMovies like this
  23. The Party 2 (1982)

    After moving to a new city, a young French teenage girl falls in love with a boy and thinks of having sex with him, since her girl friends have already done it.

    Why it matches: Similar story and style · both comedy & romance

    Popcorn FlickMovies like this
  24. Donkey Skin (1970)

    A fairy godmother helps a princess disguise herself so she won't have to marry her father.

    Why it matches: Similar story and style · both comedy & romance

    Worth the HypeMovies like this
  25. Angelina, o El honor de un brigadier (1935)

    Madrid, Spain, 1880. Angelina, daughter of the pompous Brigadier Marcial, is tempted by the womanizer Germán, who asks her to run away together, just after her boyfriend, Rodolfo, asks her to do exactly the same thing with him.

    Why it matches: Similar story and style · both comedy & romance

  26. Father's Little Dividend (1951)

    Newly married Kay Dunstan announces that she and her husband are having a baby, leaving her father to come to grips with the fact that he will soon be a granddad.

    Why it matches: Similar story and style · both romance & comedy

    Popcorn FlickMovies like this
  27. Tortilla Soup (2001)

    A Mexican-American master chef and father to three daughters has lost his taste for food but not for life.

    Why it matches: Similar story and style · both comedy & romance

    Popcorn FlickMovies like this
  28. The In-Laws (2003)

    Right before his daughter's wedding, a mild-mannered foot doctor discovers that his new in-laws are international smugglers.

    Why it matches: Similar story and style · both comedy

  29. Le Gendarme de Saint-Tropez (1964)

    The ambitious police officer Cruchot is transferred to St. Tropez. He's struggling with crimes such as persistent nude swimming, but even more with his teenage daughter, who's trying to impress her rich friends by telling them her father was a millionaire and owned a yacht in the harbor.

    Why it matches: Similar story and style · both comedy

    Worth the HypeMovies like this
  30. Father of the Bride (1991)

    George Banks is an ordinary, middle-class man whose 22 year-old daughter Annie has decided to marry a man from an upper-class family, but George can't think of what life would be like without his daughter. His wife tries to make him happy for Annie, but when the wedding takes place at their home and a foreign wedding planner takes over the ceremony, he becomes slightly insane.

    Why it matches: Similar story and style · both comedy

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Like Winners and Losers and something else?

Blend two favourites and we’ll find the films in between.

Frequently asked questions

What are the best movies like Winners and Losers?

The closest matches to Winners and Losers are Yoh! Bestie (2026), The Prince & Me 4: The Elephant Adventure (2010) and What's Love Got to Do with It? (2023). Below are 27 more, each with the reason it matches.

What should I watch after Winners and Losers?

Start with Yoh! Bestie (2026), the closest match to Winners and Losers.

What is the highest-rated movie like Winners and Losers?

My Little Pony: A New Generation (2021), rated 7.7/10 by 360 TMDB users.

What is the newest movie like Winners and Losers?

Yoh! Bestie (2026) is the most recent release on this list.

How are movies similar to Winners and Losers chosen?

First come films that Trakt’s viewers watch alongside Winners and Losers, 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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