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Movies Like The Billionaire

If you liked The Billionaire (2020), a comedy and drama movie directed by Michael Philip, 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. 1Cyrus

    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…

  2. 2Father of the Bride

    Father of the Bride (2022)

    ★ 6.3/10Also romance and comedy

    A father comes to grips with his daughter’s upcoming wedding through the prism of multiple relationships within a big, sprawling Cuban-American family.

  3. 3You 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…

  4. 4Delirious

    Delirious (2007)

    ★ 6.3/10Also comedy and drama

    Les, a small-time celebrity photographer desperate to make it big, befriends Toby, a homeless young man with no direction except a vague desire to become an actor. When by chance, Toby becomes romantically involved…

  5. 5The 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…

  6. 6Not Easily Broken

    Not Easily Broken (2009)

    ★ 6.3/10Also drama and romance

    A car accident and shifting affections test the bond between a married couple.

  7. 7Numb

    Numb (2007)

    ★ 5.9/10Also comedy and drama

    Hudson Milbank is a successful Hollywood screenwriter who suddenly and strangely finds himself without any emotional feelings. He tries doctor after doctor and shrink after shrink, but nothing works. The Golf Channel…

  8. 8Chéri

    Chéri (2009)

    ★ 6.1/10Also drama and comedy

    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.

  9. 9A California Christmas: City Lights

    A California Christmas: City Lights (2021)

    ★ 6.6/10Also romance and comedy

    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.

  10. 10Father 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.

  11. 11Why 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?"

  12. 12He 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…

  13. 13XX/XY

    XX/XY (2002)

    ★ 6/10Also drama and comedy

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

  14. 14Sidewalks 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…

  15. 15Is This Thing On?

    Is This Thing On? (2025)

    ★ 6.6/10Also comedy and drama

    As their marriage quietly unravels, Alex faces middle age and an impending divorce, seeking new purpose in the New York comedy scene while Tess confronts the sacrifices she made for their family—forcing them to…

  16. 16Young 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…

  17. 17Which 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…

  18. 18Hitch

    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…

  19. 19How to Please a Woman

    How to Please a Woman (2022)

    ★ 6.3/10Also romance and comedy

    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.

  20. 20Rosaline

    Rosaline (2022)

    ★ 7.1/10Also romance and drama

    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.

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