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Movies like Twenty-One (1991)

The best movies like Twenty-One (1991) are XX/XY (2002), L.A. Without a Map (1999) and Chéri (2009). If Twenty-One hooked you with its drama and comedy, these 20 similar films are what to watch next, and every pick says why it matches.

Quick picks

  1. XX/XY (2002)

    Three friends begin a dangerous three-way relationship that spirals out of control, leading to dire consequences that haunt them ten years later.

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

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  2. L.A. Without a Map (1999)

    An aspiring Hollywood actress, on a visit to a charming North England town, has a brief fling with the town undertaker, who also writes obituaries for the local paper. Returning home, where she works as a waitress at a Japanese restaurant, she tells everyone about the handsome "writer" she met on her trip. Unfortunately, he decides to follow her back to Hollywood, setting up the expected light romantic comedy with asides as the newcomer gains experience about the goings on in Hollywood.

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

  3. Chéri (2009)

    The son of a courtesan retreats into a fantasy world after being forced to end his relationship with the older woman who educated him in the ways of love.

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

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  4. Strictly Sexual (2008)

    Two successful women, sick and tired of dating and relationships, decide to keep two young men in their pool house for strictly sexual purposes.

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

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  5. A California Christmas: City Lights (2021)

    Follows Callie and Joseph one year after they fell in love, now running a dairy farm and winery, but their romance is threatened when business and family obligations call Joseph back to the city.

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

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  6. Sitting in Bars with Cake (2023)

    Extrovert Corinne convinces Jane, a shy, talented baker, to commit to a year of bringing cakes to bars, to help her meet people and build confidence. But when Corinne receives a life-altering diagnosis, the pair faces a challenge unlike anything they've experienced before.

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

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  7. How to Please a Woman (2022)

    When her all-male house-cleaning business gets out of control, a mature woman must embrace her own sexuality, if she is to make a new life for herself.

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

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  8. Love & Sex (2000)

    When her rather explicit copy is rejected, magazine journalist Kate is asked by her editor to come up with an article on loving relationships instead, and to do so by the end of the day. This gets Kate thinking back over her own various experiences, and to wondering if she is in much of a position to write on the subject.

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

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  9. Sidewalks of New York (2001)

    The film follows the marital and dating lives of three men and three women who unknowingly form a tangled web of relationships. Interspersing "man on the street" interviews with scenes from the six characters' lives, the film weaves a humorous and biting commentary on the game of love -- easy to start, hard to finish.

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

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  10. You Will Meet a Tall Dark Stranger (2010)

    Two married couples find only trouble and heartache as their complicated lives unfold. After 40 years of marriage, Alfie leaves his wife to pursue what he thinks is happiness with a call girl. His wife, Helena, reeling from abandonment, decides to follow the advice of a psychic. Sally, the daughter of Alfie and Helena, is unhappy in her marriage and develops a crush on her boss, while her husband, Roy, falls for a woman engaged to be married.

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

  11. Young People Fucking (2007)

    On a Tuesday night, five couples have separate sexual adventures. Matt and Kris, friends for years, want to have an only-once, no-strings good time. Abby and Andrew, married, celebrate his birthday, but it's marred by angst and miscommunication. Mia and Eric are exes, making sure they are over each other. Jaime and Ken work together and this is a first date. Inez and Gord invite his roommate, Dave, to join them. By the time each couple has gone through a prelude, foreplay, sex, an interlude, orgasm, and afterglow, they've answered basic questions: can sex be anonymous, are we bored, is our marriage really finished, does anyone tell the truth, and how do we make someone happy?

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

  12. He Said, She Said (1991)

    Womanising, right-wing Dan Hanson and quiet, liberal Lorie Bryer work for the Baltimore Sun. Rivals for the job of new writer of a vacant column, the paper ends up instead printing their very different opinions alongside each other, which leads to a similarly combative local TV show. At the same time their initial indifference to each other looks like it may evolve into something more romantic.

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

  13. Madame (2017)

    Anne and Bob, a well-to-do American couple, have just moved to a beautiful manor house in romantic Paris. To impress their sophisticated friends, they decide to host a lavish dinner party, but must disguise their maid as a noblewoman to even out the number of guests. When the maid runs off with a wealthy guest, Anne must chase her around Paris to thwart the joyous and unexpected love affair.

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

  14. Rosaline (2022)

    Left heartbroken after Romeo begins to pursue her cousin Juliet, Rosaline schemes to foil the famous romance and win back her guy in this comedic twist of Shakespeare's Romeo and Juliet.

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

    Worth the HypeMovies like this
  15. The Diary of a Chambermaid (1946)

    Celestine, the chamber-maid, has a new job in the country, at the Lanlaires. She has decided to use her beauty to seduce a wealthy man, but Mr. Lanlaire is not a right choice: the house is firmly controlled by Madame Lanlaire, helped by the strange valet Joseph. Then she tries the neighbour, former officer Mauger. This seems to work. But soon the son of the Lanlaires comes back. He is young, attractive and does not share his mother's antirepublican opinions. So Celestine's beauty attracts Captain Mauger, young Georges Lanlaire, and Joseph. Three men, from three different social classes, with three different conceptions of life. Will Celestine be able to convince Georges of her sincerity?

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

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  16. Which Brings Me to You (2023)

    Two romantic burnouts, Jane and Will, are immediately drawn to each other at a mutual friend’s wedding. After a disastrous hookup in the coatroom, the two spend the next 24 hours together, trading candid confessions of messy histories and heartbreak, on the off chance that this fling might be the real thing.

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

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  17. Enemies, a Love Story (1989)

    A ghostwriter finds himself romantically involved with his current wife, a married woman and his long-vanished wife.

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

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  18. Camille (2008)

    A twisted honeymoon adventure about a young couple on their way to Niagara Falls.

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

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  19. ATL (2006)

    As four friends prepare for life after high school, different challenges bring about turning points in each of their lives. The dramas unfold and resolve at their local rollerskating rink, Cascade.

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

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  20. 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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Like Twenty-One and something else?

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

Frequently asked questions

What are the best movies like Twenty-One?

The closest matches to Twenty-One are XX/XY (2002), L.A. Without a Map (1999) and Chéri (2009). Below are 17 more, each with the reason it matches.

What should I watch after Twenty-One?

Start with XX/XY (2002), the closest match to Twenty-One.

What is the highest-rated movie like Twenty-One?

Rosaline (2022), rated 7.1/10 by 346 TMDB users.

What is the newest movie like Twenty-One?

Which Brings Me to You (2023) is the most recent release on this list.

Are there English movies like Twenty-One?

Yes: XX/XY (2002), L.A. Without a Map (1999) and Chéri (2009).

How are movies similar to Twenty-One chosen?

First come films that Trakt’s viewers watch alongside Twenty-One, 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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