Movies like Playboy Video Playmate Calendar 1999 (1998)
The best movies like Playboy Video Playmate Calendar 1999 (1998) are Aroused (2013), Madonna: Truth or Dare (1991) and Come See Me in the Good Light (2025). If Playboy Video Playmate Calendar 1999 hooked you with its documentary, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedSly (2023)7.2/10 from 248 votes
- NewestLouis Theroux: Inside the Manosphere (2026)Released 2026
Aroused (2013)
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 about their lives are revealed, from why they chose the business of sex to how they got into it in the first place. These porn stars have always been discreet about their private lives in the past, yet Anderson has a way of opening up a dialog allowing them to share more than just their naked skin on screen. Their true inner vulnerability is touching, yet the characters they have created are confident and intoxicating. Once you hear their stories, you'll never look at them in the same way again.
Why it matches: Recommended by TMDB viewers · both documentary
SnoozefestMovies like thisMadonna: Truth or Dare (1991)
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 in black and white, with the concert pieces in glittering MTV color, it is an intimate look at the work of the icon, from a prayer circle before each performance to bed games with the dance troupe afterwards.
Why it matches: Recommended by TMDB viewers · both documentary
Popcorn FlickMovies 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 thisBettie Page Reveals All (2013)
The world's greatest pin-up model and cult icon, Bettie Page, recounts the true story of how her free expression overcame government witch-hunts to help launch America's sexual revolution. When she saw the film The Notorious Bettie Page, produced by HBO in 2006, the main person concerned reacted unequivocally: “Lies! Lies!” In a long interview recorded shortly before her death, the woman who entered the collective unconscious as the ultimate pin-up gave her version of events to director Mark Mori. In a gravelly voice, Bettie Page tells her own story and lifts the veil on areas often hidden by images that have made so many men and women fantasize since the 1950s: her abused childhood, an eclipse that lasted forty years, her mental illness. Through testimonies and unpublished archives, this documentary brings back to life a body and a face endlessly declined before our eyes, just as Bettie wanted: “I would like people to remember me as I was in the photos.”
Why it matches: Recommended by TMDB viewers · both documentary
Popcorn FlickMovies like thisStrip Down, Rise Up (2021)
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 reclaim themselves. The film also gives a rare window into the world of Pole artistry and expression.
Why it matches: Recommended by TMDB viewers · both documentary
Popcorn FlickMovies like thisMapplethorpe: Look at the Pictures (2016)
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 century. Openly gay, Mapplethorpe took images of male sex, nudity, and fetish to extremes that resulted in his work still being labelled by some as pornography masquerading as art. But less talked about are the more serene, yet striking portraits of flowers, sculptures, and perfectly framed human forms that are equally pioneering and powerful.
Why it matches: Recommended by TMDB viewers · both documentary
Popcorn FlickMovies like thisSly (2023)
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.
Why it matches: Recommended by TMDB viewers · both documentary
Worth the HypeMovies 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 thisMatangi / Maya / M.I.A. (2018)
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.
Why it matches: Recommended by TMDB viewers · both documentary
Worth the HypeMovies like thisLouis Theroux: Inside the Manosphere (2026)
With rare access and no holds barred, the acclaimed documentarian investigates a growing ultra-masculine network and its controversial influencers.
Why it matches: Recommended by TMDB viewers · both documentary
Popcorn FlickMovies 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 thisOrgasm Inc: The Story of OneTaste (2022)
A sexual wellness company gains fame and followers, then members come forward with shocking allegations.
Why it matches: Recommended by TMDB viewers · both documentary
Popcorn FlickMovies like thisHot Girls Wanted (2015)
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.
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 thisBeyond the Mat (1999)
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.
Why it matches: Recommended by TMDB viewers · both documentary
Worth the HypeMovies like thisGorillaz: Reject False Icons (2019)
Focused on the life of the band and their collaborators over the 3 vital years in which they developed critically acclaimed albums, 'Humanz' and 'The Now Now', and undertook their most ambitious world tour to date.
Why it matches: Recommended by TMDB viewers · both documentary
Worth the HypeMovies like thisWelcome to Chechnya (2020)
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 remarkable approach to protecting anonymity exposes this under-reported atrocity–and an extraordinary group of people confronting evil.
Why it matches: Recommended by TMDB viewers · both documentary
Worth the HypeMovies like thisGeneration Iron (2013)
Generation Iron - examines the professional sport of bodybuilding today and gives the audience front row access to the lives of the top 7 bodybuilders in the sport as they train to compete in the world's most premiere bodybuilding stage - Mr. Olympia.
Why it matches: Recommended by TMDB viewers · both documentary
Popcorn FlickMovies like thisFacing Ali (2009)
Ten of Muhammad Ali's former rivals pay tribute to the three-time world heavyweight champion.
Why it matches: Recommended by TMDB viewers · both documentary
Worth the HypeMovies like thisGirl Rising (2013)
Nine filmmakers each profile a young girl from a different part of the world to weave a global tapestry of youth in the 21st century.
Why it matches: Recommended by TMDB viewers · both documentary
Worth the HypeMovies like thisPlayboy: How to Reawaken Your Sexual Powers (1993)
Couples learn how to reawaken their sexual desires.
Why it matches: Similar story and style · both documentary
Playboy Intimate Secrets: How Women Love to Be Loved (TBA)
How Women Love to Be Loved
Why it matches: Similar story and style · both documentary
Playboy: Farmers' Daughters (1986)
Go country with five corn-fed cuties from the hometowns of America's heartland.
Why it matches: Similar story and style · both documentary
Slave Trade in the World Today (1964)
The film documents modern slave trade through a number of African countries, under dictatorship rule. The filming was conducted both in public places, and sometimes with the use of hidden cameras, for high impact scenes of nudity, sex, and violence - and a few surprises, as slaves made out of peregrins to Asia, and slave traders paid in traveller checks.
Why it matches: Similar story and style · both documentary
Thinking XXX (2004)
For a book project, photographer Timothy Greenfield-Sanders took photographs of 30 stars of adult movies, each pair of photographs in the same pose, clothed and nude. This film records the photo shoots and includes interviews with the performers and commentary from eight writers (and John Waters). The actors and writers discuss economics, nudity and exhibitionism, careers, and private lives.
Why it matches: Similar story and style · both documentary
SnoozefestMovies like thisSensual Massage: The Touch of Love (1980)
Massage can be a thoroughly sensual experience for two people, providing pleasure though touch. The Touch of Love... Massage presents a simple and beautiful way for adults to learn the techniques of full body massage. The steps involved in giving and receiving a massage are portrayed as nude couples demonstrate how to stroke and relax each area of the body. This videodisc invites you to learn and experience, in the privacy of your home, the art of sensual massage--a special form of physical communication.
Why it matches: Similar story and style · both documentary
Soft Bodies: Pillow Talk (1996)
Snuggle Up with Becky LeBeau and three of her voluptuous playmates for an intimate tumble between the sheets that is sure to make some feathers fly. Whether they're on an outback camping adventure or taking an in-house bubbly bath, Becky and her pals are sure to entertain..
Why it matches: Similar story and style · both documentary
Bare (2020)
The tendency in the world is right-wing, neo-liberal, and people are more controlled. We have less liberty even if we think we have more. The last territory where we can be ourselves and where we can have full freedom is our own body. The documentary "BARE" focuses on male nudity in the modern dance. The story follows a well-known Belgian choreographer Thierry Smits through a process of building his new creation with a group of male dancers performing bare naked.
Why it matches: Similar story and style · both documentary
Anamorphosis (1993)
The Quays' interest in esoteric illusions finds its perfect realization in this fascinating animated lecture on the art of anamorphosis. This artistic technique, often used in the 16th- and 17th centuries, utilizes a method of visual distortion with which paintings, when viewed from different angles, mischievously revealed hidden symbols.
Why it matches: Similar story and style · both documentary
Naked Parents (2008)
Documentary about children who have naturist parents.
Why it matches: Similar story and style · both documentary
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Frequently asked questions
What are the best movies like Playboy Video Playmate Calendar 1999?
The closest matches to Playboy Video Playmate Calendar 1999 are Aroused (2013), Madonna: Truth or Dare (1991) 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 Video Playmate Calendar 1999?
Start with Aroused (2013), the closest match to Playboy Video Playmate Calendar 1999.
What is the highest-rated movie like Playboy Video Playmate Calendar 1999?
Sly (2023), rated 7.2/10 by 248 TMDB users.
What is the newest movie like Playboy Video Playmate Calendar 1999?
Louis Theroux: Inside the Manosphere (2026) is the most recent release on this list.
Are there English movies like Playboy Video Playmate Calendar 1999?
Yes: Aroused (2013), Madonna: Truth or Dare (1991) and Come See Me in the Good Light (2025).
How are movies similar to Playboy Video Playmate Calendar 1999 chosen?
First come films that Trakt’s viewers watch alongside Playboy Video Playmate Calendar 1999, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.