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Movies Like Twelfth Night, or What You Will

If you liked Twelfth Night, or What You Will (2003), a comedy and drama movie directed by Tim Supple, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

  1. 1The Other Sister

    The Other Sister (1999)

    ★ 6.4/10Also comedy and drama

    A mentally challenged girl proves herself to be every bit as capable as her "perfect" sister when she moves into an apartment and begins going to college.

  2. 2The Best You Can

    The Best You Can (2025)

    ★ 7/10Also comedy and romance

    Cynthia Rand is a buttoned-up New Yorker married to a brilliant professor 25 years her senior. She begins feeling the effects of her husband’s advancing age on their relationship, just as her world is turned upside…

  3. 3Love Don't Co$t a Thing

    Love Don't Co$t a Thing (2003)

    ★ 7.7/10Also comedy and drama

    A high school outcast pays a cheerleader to pose as his girlfriend so he can be considered cool.

  4. 4He Said, She Said

    He Said, She Said (1991)

    ★ 5.9/10Also comedy and drama

    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…

  5. 5Father of the Bride

    Father of the Bride (1950)

    ★ 7/10Also comedy and romance

    Proud father Stanley Banks remembers the day his daughter, Kay, got married. Starting when she announces her engagement through to the wedding itself, we learn of all the surprises and disasters along the way.

  6. 6Sidewalks of New York

    Sidewalks of New York (2001)

    ★ 6.1/10Also comedy and drama

    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…

  7. 7The Giant Mechanical Man

    The Giant Mechanical Man (2012)

    ★ 6.5/10Also comedy and drama

    An offbeat romantic comedy about a silver-painted street performer and the soft spoken zoo worker who falls for him.

  8. 8Love in Taipei

    Love in Taipei (2023)

    ★ 6.8/10Also romance and comedy

    A young American woman is sent by her parents to a cultural immersion program in Taipei where she begins a new journey of self-discovery and romance.

  9. 9Why Did I Get Married Again?

    Why Did I Get Married Again? (2026)

    ★ 6.8/10Also comedy and romance

    The couples reunite for the destination wedding of Marcus and Angela's daughter, bringing drama old and new as they ask, "Why did we get married again?"

  10. 10Enemies, a Love Story

    Enemies, a Love Story (1989)

    ★ 6.2/10Also comedy and drama

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

  11. 11You Will Meet a Tall Dark Stranger

    You Will Meet a Tall Dark Stranger (2010)

    ★ 5.9/10Also comedy and drama

    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…

  12. 12Cyrus

    Cyrus (2010)

    ★ 5.9/10Also comedy and drama

    With John's social life at a standstill and his ex-wife about to get remarried, a down on his luck divorcée finally meets the woman of his dreams, only to discover she has another man in her life - her son. Before…

  13. 13Hitch

    Hitch (2005)

    ★ 6.6/10Also comedy and drama

    Dating coach Alex 'Hitch' Hitchens mentors a bumbling client, Albert, who hopes to win the heart of the glamorous Allegra Cole. While Albert makes progress, Hitch faces his own romantic setbacks when proven techniques…

  14. 14Which Brings Me to You

    Which Brings Me to You (2023)

    ★ 6.3/10Also romance and comedy

    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…

  15. 15Coyote Ugly

    Coyote Ugly (2000)

    ★ 6.3/10Also comedy and drama

    Graced with a velvet voice, 21-year-old Violet Sanford heads to New York to pursue her dream of becoming a songwriter only to find her aspirations sidelined by the accolades and notoriety she receives at her "day" job…

  16. 16Newness

    Newness (2017)

    ★ 6.1/10Also romance and drama

    In contemporary Los Angeles, two millennials navigating a social media–driven hookup culture begin a relationship that pushes both emotional and physical boundaries.

  17. 17Young People Fucking

    Young People Fucking (2007)

    ★ 5.9/10Also comedy and drama

    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…

  18. 18Peace, Love & Misunderstanding

    Peace, Love & Misunderstanding (2011)

    ★ 5.8/10Also comedy and drama

    A conservative lawyer named Diane takes her two teenage children Jake and Zoe to meet their estranged, hippie grandmother in Woodstock after her husband asks for a divorce.

  19. 19Breaking & Exiting

    Breaking & Exiting (2018)

    ★ 6/10Also comedy and drama

    Harry, a charming house thief, gets more than he bargains for during an attempted burglary when he stumbles upon Daisy and decides to save her from herself, sending both of them into a darkly comedic journey of self…

  20. 20The Baltimorons

    The Baltimorons (2025)

    ★ 6.3/10Also comedy and drama

    A newly sober man's Christmas Eve dental emergency leads to an unexpected romance with his older dentist as they explore Baltimore together.

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