Movies Like Playboy's Girlfriends

If you liked Playboy's Girlfriends (1998), a documentary and romance movie, 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
A Complete History of My Sexual Failures (2008)
★ 6.2/10Also documentary and romance
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…
2
Come See Me in the Good Light (2025)
★ 7.1/10Also documentary
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.
3
Avatar: The Deep Dive - A Special Edition of 20/20 (2022)
★ 7.2/10Also documentary
An inside look at one of the most anticipated movie sequels ever with James Cameron and cast.
4
Harmontown (2014)
★ 6.6/10Also documentary
A comedic, brutally honest documentary following self-destructive TV writer Dan Harmon as he takes his live podcast on a national tour.
5
Katy Perry: Part of Me (2012)
★ 7.1/10Also documentary
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…
6
My Mom Jayne (2025)
★ 8/10Also documentary
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…
7
Selena Gomez: My Mind & Me (2022)
★ 8.4/10Also documentary
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…
8
Justin Bieber's Believe (2013)
★ 6.9/10Also documentary
A backstage and on-stage look at Justin Bieber during his rise to super stardom.
9
No Half Measures: Creating the Final Season of Breaking Bad (2013)
★ 8.5/10Also documentary
A documentary about the making of season five of the acclaimed AMC series Breaking Bad.
10
Pamela, a love story (2023)
★ 7/10Also documentary
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.
11
The Last Repair Shop (2024)
★ 7.5/10Also documentary
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…
12
As I Was Moving Ahead Occasionally I Saw Brief Glimpses of Beauty (2000)
★ 7.8/10Also documentary
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.
13
Billie Eilish - Hit Me Hard and Soft: The Tour (Live in 3D) (2026)
★ 8.4/10Also documentary
Captured during Billie Eilish's sold-out world tour, a concert experience from one of the most celebrated and successful artists of her generation, presented in immersive 3D.
14
Biggie: I Got a Story to Tell (2021)
★ 7.1/10Also documentary
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…
15
Western Stars (2019)
★ 7/10Also documentary
The incomparable Bruce Springsteen performs his critically acclaimed latest album and muses on life, rock, and the American dream, in this intimate and personal concert film co-directed by Thom Zimny and Springsteen…
16
American Symphony (2023)
★ 6.5/10Also documentary
Musician Jon Batiste attempts to compose a symphony as his wife, writer Suleika Jaouad, undergoes cancer treatment.
17
Marvel's Behind the Mask (2021)
★ 7/10Also documentary
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…
18
Halftime (2022)
★ 6.8/10Also documentary
Global superstar Jennifer Lopez reflects on her multifaceted career and the pressure of life in the spotlight in this intimate documentary.
19
A Toxic Love Story (2026)
★ 6.4/10Also documentary
A string of threatening emails escalates into a revenge plot involving a newly married US marshal and his ex-girlfriend.
20
Crazy Love (2007)
★ 6.5/10Also documentary and romance
Filmmaker Dan Klores examines the strange love affair of Burt Pugach and Linda Riss. Pugach is a successful attorney in 1950s New York when he meets much-younger Riss. The pair date, but Riss breaks off contact with…