Movies Like Playboy Video Playmate Calendar 1999

If you liked Playboy Video Playmate Calendar 1999 (1998), a documentary movie directed by Scott Allen, 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
Aroused (2013)
★ 5.9/10Also documentary
Get up close and personal with 16 of the most successful women in the adult film industry as they shed their clothes for an intimate photo shoot with director Deborah Anderson. As questions are asked, personal stories…
2
Madonna: Truth or Dare (1991)
★ 6.2/10Also documentary
From the rains of Japan, through threats of arrest for 'public indecency' in Canada, and a birthday tribute to her father in Detroit, this documentary follows Madonna on her 1990 'Blond Ambition' concert tour. Filmed…
3
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.
4
Sly (2023)
★ 7.2/10Also documentary
His love of film began as an escape from a rocky childhood. From underdog to Hollywood legend, Sylvester Stallone tells his story in this documentary.
5
Matangi / Maya / M.I.A. (2018)
★ 7.5/10Also documentary
Drawn from a never before seen cache of personal footage spanning decades, this is an intimate portrait of the Sri Lankan artist and musician who continues to shatter conventions.
6
Shawn Mendes: In Wonder (2020)
★ 8.1/10Also documentary
A portrait of singer-songwriter Shawn Mendes' life, chronicling the past few years of his rise and journey.
7
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.
8
Strip Down, Rise Up (2021)
★ 6.5/10Also documentary
The feature documentary follows women of all walks of life, all ages and ethnic backgrounds, as they shed trauma, body image shame, sexual abuse and other issues locked in their bodies, and embark on a journey to…
9
Louis Theroux: Inside the Manosphere (2026)
★ 6.6/10Also documentary
With rare access and no holds barred, the acclaimed documentarian investigates a growing ultra-masculine network and its controversial influencers.
10
Orgasm Inc: The Story of OneTaste (2022)
★ 6.1/10Also documentary
A sexual wellness company gains fame and followers, then members come forward with shocking allegations.
11
Hot Girls Wanted (2015)
★ 6.1/10Also documentary
A first-ever look at the realities of the professional “amateur” porn world and the steady stream of 18-to-19-year old girls entering into it.
12
X-Rated 2: The Greatest Adult Stars of All Time (2016)
★ 6.8/10Also documentary
Documentary sequel that offers a close-up look into the personal lives of the legendary porn stars who've survived the test of time and influenced popular culture. Blends rare interviews with erotic clips and…
13
Mapplethorpe: Look at the Pictures (2016)
★ 6.9/10Also documentary
Nude men in rubber suits, close-ups of erections, objects shoved in the most intimate of places—these are photographs taken by Robert Mapplethorpe, known by many as the most controversial photographer of the twentieth…
14
Welcome to Chechnya (2020)
★ 7/10Also documentary
This searing investigative work shadows a group of activists risking unimaginable peril to confront the ongoing anti-LGBTQ program raging in the repressive and closed Russian republic. Unfettered access and a…
15
You Can See Everything (2026)
★ 8.9/10Also documentary
Thirty-four days before she's sent to prison, notorious Silicon Valley founder Elizabeth Holmes invites a skeptical film crew to document her every move. What begins as an intimate portrait of an enigmatic felon…
16
Beyond the Mat (1999)
★ 7.3/10Also documentary
A heartfelt documentary focusing on the day-to-day lives of professional wrestlers, some on the rise, some on the wane, and others fighting for their lives.
17
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.
18
Inside Deep Throat (2005)
★ 6.4/10Also documentary
In 1972, a seemingly typical shoestring budget pornographic film was made in a Florida hotel: "Deep Throat," starring Linda Lovelace. This film would surpass the wildest expectation of everyone involved to become one…
19
Anna Nicole Smith: You Don't Know Me (2023)
★ 6.1/10Also documentary
From the heights of her modeling fame to her tragic death, this documentary reveals Anna Nicole Smith through the eyes of the people closest to her.
20
The Curse of the Dragon (1993)
★ 7.2/10Also documentary
A 1993 documentary film about Bruce Lee. The film includes interviews from some of his fellow students and opponents who worked alongside him in his movies.