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Movies Like Milk Money

If you liked Milk Money (1994), a comedy and romance movie directed by Richard Benjamin, 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. 1A Night at the Roxbury

    A Night at the Roxbury (1998)

    ★ 6.6/10Also comedy and romance

    Despite being well into adulthood, brothers Doug and Steve Butabi still live at home and work in the flower shop owned by their dad. They exist only to hit on women at discos, though they're routinely unsuccessful…

  2. 2City Island

    City Island (2009)

    ★ 6.9/10Also drama and comedy

    The Rizzos, a family who doesn't share their habits, aspirations, and careers with one another, find their delicate web of lies disturbed by the arrival of a young ex-con brought home by Vince, the patriarch of the…

  3. 3The Escort

    The Escort (2015)

    ★ 6/10Also drama and comedy

    Desperate for a good story, a sex-addicted journalist throws himself into the world of high-class escorts when he starts following a Stanford-educated prostitute.

  4. 4Fallen Angel

    Fallen Angel (1945)

    ★ 6.6/10Also drama and romance

    An unemployed drifter, Eric Stanton wanders into a small California town and begins hanging around the local diner. While Eric falls for the lovely waitress Stella, he also begins romancing a quiet and well-to-do woman…

  5. 5Madea Goes to Jail

    Madea Goes to Jail (2009)

    ★ 6.5/10Also comedy and drama

    After a high-speed car chase, Madea winds up behind bars because her quick temper gets the best of her. Meanwhile, Assistant District Attorney Josh Hardaway lands a case that's too personal to handle: that of a young…

  6. 6Chéri

    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.

  7. 7Madea's Family Reunion

    Madea's Family Reunion (2006)

    ★ 6.3/10Also drama and comedy

    Southern matriarch Madea has a lot on her plate. Her nieces, Vanessa and Lisa, have relationship troubles - Vanessa moves into Madea's house with her 2 young children and Lisa is engaged to a controlling man that her…

  8. 8Love Everlasting

    Love Everlasting (2016)

    ★ 7.4/10Also romance and drama

    Bridger is a young outsider who's always wanted more. He and his mother flee an abusive home, eventually finding a small town in the middle of nowhere. Once there, Bridger finds true acceptance with another misfit.

  9. 9Fools Rush In

    Fools Rush In (1997)

    ★ 6.5/10Also comedy and drama

    After a one night stand with Alex, Isabel realizes that she is pregnant and they decide to get married. However, along with the marriage comes compromise of one's own cultural traditions.

  10. 10Only the Lonely

    Only the Lonely (1991)

    ★ 6.2/10Also comedy and romance

    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…

  11. 11Which 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…

  12. 12It Ends with Us

    It Ends with Us (2024)

    ★ 6.9/10Also drama and romance

    When a woman's first love suddenly reenters her life, her relationship with a charming, but abusive neurosurgeon is upended, and she realizes she must learn to rely on her own strength to make an impossible choice for…

  13. 13Heartbreakers

    Heartbreakers (2001)

    ★ 6.2/10Also comedy and romance

    Max and Page are a brilliant mother/daughter con team who have their grift down to a fine science. Max targets wealthy, willing men and marries them. Page then seduces them, and Max catches her husband in the act. Then…

  14. 14SubUrbia

    SubUrbia (1997)

    ★ 6.2/10Also comedy and drama

    A group of suburban teenagers try to support each other through the difficult task of becoming adults.

  15. 15Café Society

    Café Society (2016)

    ★ 6.4/10Also comedy and drama

    The story of a young man who arrives in Hollywood during the 1930s hoping to work in the film industry, falls in love, and finds himself swept up in the vibrant café society that defined the spirit of the age.

  16. 16Sabrina

    Sabrina (1954)

    ★ 7.5/10Also comedy and romance

    After two years in Paris, chauffeur's daughter Sabrina returns home elegantly transformed and immediately catches the attention of David, the playboy son of her father's rich employers. David woos and wins Sabrina, who…

  17. 17The 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.

  18. 18The Cable Guy

    The Cable Guy (1996)

    ★ 6/10Also comedy and drama

    When recently single Steven moves into his new apartment, cable guy Chip comes to hook him up—and doesn't let go. Initially, Chip is just overzealous in his desire to be Steven's pal, but when Steven tries to end the…

  19. 19Arthur

    Arthur (1981)

    ★ 6.5/10Also comedy and drama

    Arthur is a 30-year-old child who will inherit $750 million if he complies with his family's demands and marries the woman of their choosing.

  20. 20She's Funny That Way

    She's Funny That Way (2015)

    ★ 5.9/10Also comedy and romance

    On the set of a playwright's new project, a love triangle forms between his wife, her ex-lover, and the call girl-turned-actress cast in the production.

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