Movies like Playboy's Girlfriends (1998)
The best movies like Playboy's Girlfriends (1998) are A Complete History of My Sexual Failures (2008), Katy Perry: Part of Me (2012) and Come See Me in the Good Light (2025). If Playboy's Girlfriends hooked you with its documentary and romance, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedSelena Gomez: My Mind & Me (2022)8.4/10 from 623 votes
- NewestCome See Me in the Good Light (2025)Released 2025
A Complete History of My Sexual Failures (2008)
The egocentric documentary-maker Chris Waitt traces his romantic ineptitude and sexual impotence through awkward interviews with irate ex-girlfriends and stunts involving S&M parlours, Harley Street doctors and Viagra overdoses. The results are often hilarious, sometimes moving and speak directly to the hapless paramour in all of us.
Why it matches: Recommended by TMDB viewers · both documentary & romance
Popcorn FlickMovies like thisKaty Perry: Part of Me (2012)
Giving fans unprecedented access to the real life of the music sensation, Katy Perry: Part of Me exposes the hard work, dedication and phenomenal talent of a girl who remained true to herself and her vision in order to achieve her dreams. Featuring rare behind-the-scenes interviews, personal moments between Katy and her friends, and all-access footage of rehearsals, choreography, Katy’s signature style and more, Katy Perry: Part of Me reveals the singer’s unwavering belief that if you can be yourself, then you can be anything.
Why it matches: Recommended by TMDB viewers · both documentary
Worth the HypeMovies like thisCome See Me in the Good Light (2025)
In an intimate and joyful story of love in the face of loss, celebrated poets Andrea Gibson and Megan Falley find strength—and unexpected hilarity—in what might be their final year together.
Why it matches: Recommended by TMDB viewers · both documentary
Worth the HypeMovies like thisBiggie: I Got a Story to Tell (2021)
Christopher Wallace, AKA The Notorious B.I.G., remains one of Hip-Hop’s icons, renowned for his distinctive flow and autobiographical lyrics. This documentary celebrates his life via rare behind-the-scenes footage and the testimonies of his closest friends and family.
Why it matches: Recommended by TMDB viewers · both documentary
Worth the HypeMovies like thisAvatar: The Deep Dive - A Special Edition of 20/20 (2022)
An inside look at one of the most anticipated movie sequels ever with James Cameron and cast.
Why it matches: Recommended by TMDB viewers · both documentary
Worth the HypeMovies like thisThe Last Repair Shop (2024)
In a warehouse in the heart of Los Angeles, a dwindling handful of devoted craftspeople maintain more than 80,000 student musical instruments, the largest remaining workshop in America of its kind. Meet four unforgettable characters whose broken-and-repaired lives have been dedicated to bringing so much more than music to the schoolchildren of this city.
Why it matches: Recommended by TMDB viewers · both documentary
Worth the HypeMovies like thisHarmontown (2014)
A comedic, brutally honest documentary following self-destructive TV writer Dan Harmon as he takes his live podcast on a national tour.
Why it matches: Recommended by TMDB viewers · both documentary
Popcorn FlickMovies like thisJustin Bieber's Believe (2013)
A backstage and on-stage look at Justin Bieber during his rise to super stardom.
Why it matches: Recommended by TMDB viewers · both documentary
Popcorn FlickMovies like thisMy Mom Jayne (2025)
Through deeply personal interviews with her siblings and an examination of the photographs, letters, and belongings left behind, Mariska assembles a new portrait of her mother Jayne Mansfield, an extraordinary and complex woman.
Why it matches: Recommended by TMDB viewers · both documentary
Absolute CinemaMovies like thisMarvel's Behind the Mask (2021)
A documentary special that explores the power of identity behind the iconic superheroes we know and love today. These legendary Marvel creations and stories have not only reflected the world outside our window – they have become a reflection of our own identities and who we truly are.
Why it matches: Recommended by TMDB viewers · both documentary
Worth the HypeMovies like thisSelena Gomez: My Mind & Me (2022)
After years in the limelight, Selena Gomez achieves unimaginable stardom. But just as she reaches a new peak, an unexpected turn pulls her into darkness. This uniquely raw and intimate documentary spans her six-year journey into a new light.
Why it matches: Recommended by TMDB viewers · both documentary
Absolute CinemaMovies like thisShawn Mendes: In Wonder (2020)
A portrait of singer-songwriter Shawn Mendes' life, chronicling the past few years of his rise and journey.
Why it matches: Recommended by TMDB viewers · both documentary
Absolute CinemaMovies like thisAmerican Symphony (2023)
Musician Jon Batiste attempts to compose a symphony as his wife, writer Suleika Jaouad, undergoes cancer treatment.
Why it matches: Recommended by TMDB viewers · both documentary
Popcorn FlickMovies like thisPamela, a love story (2023)
In her own words, through personal video and diaries, Pamela Anderson shares the story of her rise to fame, rocky romances and infamous sex tape scandal.
Why it matches: Recommended by TMDB viewers · both documentary
Worth the HypeMovies like thisLove, Marilyn (2013)
Using the book 'Fragments', which collects Marilyn Monroe's poems, notes and letters, and with participation from the Arthur Miller and Truman Capote estates who have contributed more material, each of the actresses will embody the legend at various stages in her life.
Why it matches: Recommended by TMDB viewers · both documentary
Popcorn FlickMovies like thisHalftime (2022)
Global superstar Jennifer Lopez reflects on her multifaceted career and the pressure of life in the spotlight in this intimate documentary.
Why it matches: Recommended by TMDB viewers · both documentary
Popcorn FlickMovies like thisEnd of the Century: The Story of the Ramones (2003)
A years-in-the-making documentary on the legendary punk band the Ramones. Through a mixture of archival footage, archival and new interviews with all members of the band's various lineups, and new interviews with a number of their contemporaries, the film traces the peaks and valleys the band experienced over the course of its 20-plus year career before disbanding in 1995.
Why it matches: Recommended by TMDB viewers · both documentary
Worth the HypeMovies like thisAs I Was Moving Ahead Occasionally I Saw Brief Glimpses of Beauty (2000)
A compilation of over 30 years of private home movie footage shot by Lithuanian-American avant-garde director Jonas Mekas, assembled by Mekas "purely by chance", without concern for chronological order.
Why it matches: Recommended by TMDB viewers · both documentary
Worth the HypeMovies like thisNo Half Measures: Creating the Final Season of Breaking Bad (2013)
A documentary about the making of season five of the acclaimed AMC series Breaking Bad.
Why it matches: Recommended by TMDB viewers · both documentary
Absolute CinemaMovies like thisThe Decline of Western Civilization Part III (1998)
A musical study of Los Angeles in the late 90s, where homeless teens roam the streets and profess to live a punk lifestyle of music, drugs, and flouting authority.
Why it matches: Recommended by TMDB viewers · both documentary
Popcorn FlickMovies like thisImagine Me & You (2006)
During her wedding ceremony, Rachel notices Luce in the audience and feels instantly drawn to her. The two women become close friends, and when Rachel learns that Luce is a lesbian, she realizes that despite her happy marriage to Heck, she is falling for Luce. As she questions her sexual orientation, Rachel must decide between her stable relationship with Heck and her exhilarating new romance with Luce.
Why it matches: Similar story and style · both romance
Worth the HypeMovies like thisChasing Amy (1997)
Holden and Banky are comic book artists. Everything is going good for them until they meet Alyssa, also a comic book artist. Holden falls for her, but his hopes are crushed when he finds out she's a lesbian.
Why it matches: Similar story and style · both romance
Popcorn FlickMovies like thisAimée & Jaguar (1999)
In 1943, while the Allies are bombing Berlin and the Gestapo is purging the capital of Jews, a dangerous love affair blossoms between two women – one a Jewish member of the underground, the other an exemplar of Nazi motherhood.
Why it matches: Similar story and style · both romance
Popcorn FlickMovies like thisNina's Heavenly Delights (2006)
A feisty young woman returns to Glasgow to run her deceased father's curry house.
Why it matches: Similar story and style · both romance
Popcorn FlickMovies like thisFragment 24 (2025)
One night, contract killers Safo and Erina celebrate their latest work when they are surprised by an unusual request: a black envelope with just the signature 'V'.
Why it matches: Similar story and style · both romance
See You Soon (2025)
A woman traveling to Italy for her sister's wedding has a layover in France, where a chance encounter with a French woman sparks an instant, life-altering connection.
Why it matches: Similar story and style · both romance
D.E.B.S. (2005)
The star of a team of teenage crime fighters falls for the alluring villainess she must bring to justice.
Why it matches: Similar story and style · both romance
Popcorn FlickMovies like thisTogether (2000)
Elisabeth leaves her abusive and drunken husband Rolf, and goes to live with her brother, Göran. The year is 1975 and Göran lives in a commune called Together. Living in this leftist commune Elisabeth learns that the world can be viewed from different perspectives.
Why it matches: Similar story and style · both romance
Worth the HypeMovies like this
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Frequently asked questions
What are the best movies like Playboy's Girlfriends?
The closest matches to Playboy's Girlfriends are A Complete History of My Sexual Failures (2008), Katy Perry: Part of Me (2012) and Come See Me in the Good Light (2025). Below are 27 more, each with the reason it matches.
What should I watch after Playboy's Girlfriends?
Start with A Complete History of My Sexual Failures (2008), the closest match to Playboy's Girlfriends.
What is the highest-rated movie like Playboy's Girlfriends?
Selena Gomez: My Mind & Me (2022), rated 8.4/10 by 623 TMDB users.
What is the newest movie like Playboy's Girlfriends?
Come See Me in the Good Light (2025) is the most recent release on this list.
Are there English movies like Playboy's Girlfriends?
Yes: A Complete History of My Sexual Failures (2008), Katy Perry: Part of Me (2012) and Come See Me in the Good Light (2025).
How are movies similar to Playboy's Girlfriends chosen?
First come films that Trakt’s viewers watch alongside Playboy's Girlfriends, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.