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Movies like Why I Wore Lipstick to My Mastectomy (2006)

The best movies like Why I Wore Lipstick to My Mastectomy (2006) are Drumline: A New Beat (2014), Barbarians at the Gate (1993) and My Dinner with Hervé (2018). If Why I Wore Lipstick to My Mastectomy hooked you with its drama and comedy, these 30 similar films are what to watch next, and every pick says why it matches.

Quick picks

  1. Drumline: A New Beat (2014)

    A girl from New York attends a college in Atlanta to join their once-famous marching band.

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

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  2. Barbarians at the Gate (1993)

    F. Ross Johnson decides to buyout his own tobacco firm RJR Nabisco after the plans of the launch of his new product, a smokeless cigarette Premier, fail on account of market rumours.

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

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  3. My Dinner with Hervé (2018)

    An unlikely friendship evolves over one wild night in LA between a struggling journalist and actor Hervé Villechaize, the world's most famous gun-toting dwarf, resulting in life-changing consequences for both.

    Why it matches: Recommended by TMDB viewers · both drama

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  4. Hello Sister, Goodbye Life (2006)

    A college student must take care of her 7-year-old half sister after the death of their parents.

    Why it matches: Recommended by TMDB viewers · both drama

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  5. Rebound: The Legend of Earl 'The Goat' Manigault (1996)

    A dramatization of the life of Earl 'The Goat' Manigault (Don Cheadle), with a lot of factual based occurrences. A reformed junkie returns from prison to clean up his act and devote the rest of his life to the young kids of Harlem. 1996 was the 25th anniversary of the first tournament named after him.

    Why it matches: Recommended by TMDB viewers · both drama

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  6. Iron Jawed Angels (2004)

    Defiant young activists take the women's suffrage movement by storm, putting their lives at risk to help American women win the right to vote.

    Why it matches: Recommended by TMDB viewers · both drama

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  7. Homeless to Harvard: The Liz Murray Story (2003)

    Based on a true story. Liz Murray is a young girl who is taken care of by her loving, but drug-addicted parents. Liz becomes homeless at 15 and after a tragedy comes upon her, she begins her work to finish high school.

    Why it matches: Recommended by TMDB viewers · both drama

    Worth the HypeMovies like this
  8. Introducing Dorothy Dandridge (1999)

    An acclaimed stage performer, Dorothy still struggled with the challenge of her color, in a time that wouldn't let some stars in by the front door. Yet against the odds she beat out many more famous rivals for the role of "Carmen Jones", becoming the first black woman ever nominated for a Best Actress Academy Award. Marriages and affairs would break her heart, but her heart was strong. Seductive and easily seduced, she was born to be a star - with all the glory and all the pain of being loved, abused, cheated, glorified, undermined and undefeated. Here was a woman who wouldn't wait in the wings. Halle Berry stars as Dorothy Dandrige.

    Why it matches: Recommended by TMDB viewers · both drama

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  9. I Am Elizabeth Smart (2017)

    The story of Elizabeth Smart's kidnapping and captivity, as told from her perspective.

    Why it matches: Recommended by TMDB viewers · both drama

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  10. A Bramble House Christmas (2017)

    While settling his father’s estate, Finn Conrad becomes suspicious as to why the man left a nurse $100,000. His dad knew her for less than two months before he died. Just before Christmas, Finn wants what to reclaim what he considers his family’s money, going undercover to investigate the bed and breakfast the nurse has recently taken over. When Finn meets Willa, he discovers she’s not a conniving gold digger at all, but a woman in need who put the money to good use. When she discovers his true identity, will it keep Willa from ever trusting him again?

    Why it matches: Recommended by TMDB viewers · both drama

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  11. SubUrbia (1997)

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

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

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  12. TalhotBlond (2012)

    Thomas Montgomery, a married father of two young daughters, gets seduced by the world of online gambling and chat rooms where a virtual romance and sexual obsession ultimately leads to the murder of an innocent man.

    Why it matches: Recommended by TMDB viewers · both drama

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  13. The Christmas Shoes (2002)

    Two separate stories mesh - in the first, a young music teacher, Maggie Andrews, begins dying of a heart condition and her son Nathan tries to get a pair of Christmas shoes for her before she dies. In the second, lawyer Robert Layton and his wife Kate are slowly drifting apart and the matter comes to a head during Christmas when Kate takes over for Maggie for the school choir.

    Why it matches: Recommended by TMDB viewers · both drama

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  14. Cheaters (2000)

    In the fall of 1994, a teacher at Chicago's run-down Steinmetz High conspires with the school's academic decathlon team to cheat on an academic competition.

    Why it matches: Recommended by TMDB viewers · both drama

    Popcorn FlickMovies like this
  15. Don't Think Twice (2016)

    An improv group deals with several crises, including the loss of their lease and one member hitting the big time.

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

    Popcorn FlickMovies like this
  16. Normal (2003)

    A Midwestern husband and father announces his plan to have a sex change operation.

    Why it matches: Recommended by TMDB viewers · both drama

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  17. A Flintstones Christmas Carol (1994)

    Fred is cast as Ebenezer Scrooge in a stage adaption of the classic Christmas story, but is acting a bit stingy in real life.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  18. Closer to the Moon (2014)

    A Romanian police officer teams up with a small crew of bank robbers to pull off a heist by convincing everyone at the scene of the crime that they are only filming a movie.

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

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  19. Girl in the Box (2016)

    The true story of 20-year-old Colleen Stan, a hitchhiking woman abducted by a young couple and held captive for seven years, during which time she's tortured and forced to live as a slave to her captors.

    Why it matches: Recommended by TMDB viewers · both drama

    Popcorn FlickMovies like this
  20. Juniper (2021)

    When a self-destructive teenager is suspended from school and asked to look after his feisty alcoholic grandmother as a punishment, the crazy time they spend together turns his life around.

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

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  21. Living Proof (2008)

    Dr Dennis Slamon, an American oncologist, discovers a treatment that could possibly cure breast cancer without radiation or chemotherapy. He tries to look for ways to fund the medication.

    Why it matches: Similar story and style · both drama

  22. Pieces of April (2003)

    Quirky and rebellious April Burns lives with her boyfriend in a low-rent New York City apartment miles away from her emotionally distant family. But when she discovers that her mother has a fatal form of breast cancer, she invites the clan to her place for Thanksgiving. While her father struggles to drive her family into the city, April -- an inexperienced cook -- runs into kitchen trouble and must ask a neighbor for help.

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

    Popcorn FlickMovies like this
  23. Boobies (2025)

    A couple is making a sextape, but she has a question, and he doesn't know the answer...

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

  24. Can (2024)

    Filmmaker Kailee McGee’s world turns sideways with a late-stage breast cancer diagnosis. She’s in the middle of treatment but just beginning to reevaluate reality, love, and identity while being sick. Kailee loses track of where her cancer journey ends and her life begins. As the voice inside her head toggles between existential crisis and self-actualization, Kailee resorts to the only way she knows how to heal: figure out a way to watch a version of her journey unfold on a screen.

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

  25. Lay Lefty Down (2026)

    Two women unexpectedly unite through stories of grief and laughter, after their family throws a surprise memorial for a left breast.

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

  26. Time to Spare (2011)

    When Molly, the 21 year-old sister of Maarten, departs the family home, she leaves her older brother with empty nest syndrome. But it also opens up new opportunities for him, such as the possibility to explore his love for Arthur, a closet gay. Molly and Maarten wrestle with their personal relationships and also their relationship with one another, but fate nevertheless seems determined to strike them both down.

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

  27. My Breast (1994)

    Meredith Baxter plays Joyce Wadler in this heartwarming story of hope, courage and redemption inspired by the New York City journalist's real-life struggle with breast cancer. Stuck in a lackluster relationship with her boyfriend, she's forced to re-examine her life when she receives the troubling diagnosis.

    Why it matches: Similar story and style · both drama

  28. Viva (2026)

    After coming face to face with death, 40-year-old Nora is consumed by an urgent need to feel alive. She dives into passionate relationships with two very different men, Tom and Max, whose opposing natures reflect her own inner conflict. But when neither can fill the void, Nora is forced to face the truth, she will have to confront a deeper fear driving her hunger for life.

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

  29. Cavalcade (2001)

    Caroline, a professional horse driver, learns she has breast cancer. Avoiding dealing with it, she runs off to Switserland for a championship. Her husband, Julien, is a judge who has just given a young criminal, Pierre, leave for the day. On her way to Switserland, Caroline meets Pierre and brings him along as her horse groom. When Julien finds out about the cancer, he follows his wife to Switserland

    Why it matches: Similar story and style · both drama

  30. Time Lost, Time Found (2009)

    A woman is forced to choose between her unborn child or medical treatment for re-occuring breast cancer. Shizuku, a talented surgeon, gets pregnant. In the past ten years of her marriage, she hasn't expected a baby because of breast cancer when she was young. She is pleased for the good news with her husband Ryosuke. However, soon after that, she has a relapse of breast cancer. This is the final chance for 38-year-old Shizuku to have a baby. However, she won't be able to raise her baby after the birth. Should she give up the baby and concentrate on medical treatment? Or should she give birth to the baby even if that may shorten her life? Shizuku is afflicted with the ultimate decision. Her life is filled with difficulties, but in the end, there is a big hope remaining.

    Why it matches: Similar story and style · both drama

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Frequently asked questions

What are the best movies like Why I Wore Lipstick to My Mastectomy?

The closest matches to Why I Wore Lipstick to My Mastectomy are Drumline: A New Beat (2014), Barbarians at the Gate (1993) and My Dinner with Hervé (2018). Below are 27 more, each with the reason it matches.

What should I watch after Why I Wore Lipstick to My Mastectomy?

Start with Drumline: A New Beat (2014), the closest match to Why I Wore Lipstick to My Mastectomy.

What is the highest-rated movie like Why I Wore Lipstick to My Mastectomy?

Pieces of April (2003), rated 6.5/10 by 284 TMDB users.

What is the newest movie like Why I Wore Lipstick to My Mastectomy?

Viva (2026) is the most recent release on this list.

Are there English movies like Why I Wore Lipstick to My Mastectomy?

Yes: Drumline: A New Beat (2014), Barbarians at the Gate (1993) and My Dinner with Hervé (2018).

How are movies similar to Why I Wore Lipstick to My Mastectomy chosen?

First come films that Trakt’s viewers watch alongside Why I Wore Lipstick to My Mastectomy, 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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