Movies like Penthouse: Dear Diary (2000)
The best movies like Penthouse: Dear Diary (2000) are American Boy: A Profile of Steven Prince (1978), McQueen (2018) and 21 Up (1977). If Penthouse: Dear Diary hooked you with its documentary, these 20 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedPamela, a love story (2023)7.0/10 from 260 votes
- NewestA Toxic Love Story (2026)Released 2026
American Boy: A Profile of Steven Prince (1978)
Martin Scorsese spends an evening with larger-than-life raconteur Steven Prince—a former drug addict, road manager for Neil Diamond, and actor—as he recounts stories from his colorful life.
Why it matches: Recommended by TMDB viewers · both documentary
Popcorn FlickMovies like thisMcQueen (2018)
Alexander McQueen's rags-to-riches story is a modern-day fairy tale, laced with the gothic. Mirroring the savage beauty, boldness and vivacity of his design, this documentary is an intimate revelation of McQueen's own world, both tortured and inspired, which celebrates a radical and mesmerizing genius of profound influence.
Why it matches: Recommended by TMDB viewers · both documentary
Worth the HypeMovies like this21 Up (1977)
After another 7 year wait, director Michael Apted revisits the same group of British-born children from Seven Up! and 7 Plus Seven. The subjects are interviewed as to the changes that have occurred in their lives during the last seven years.
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 thisThe Crystal Calls - Making The Dark Crystal: Age of Resistance (2019)
Go behind the scenes with stars, puppeteers and creators as they bring Jim Henson's magical world of Thra back to life in a sweeping fantasy series.
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 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 thisAnna Nicole Smith: You Don't Know Me (2023)
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.
Why it matches: Recommended by TMDB viewers · both documentary
Popcorn FlickMovies like thisEx Libris: The New York Public Library (2017)
A documentary about how a dominant cultural and demographic institution both sustains their traditional activities and adapts to the digital revolution.
Why it matches: Recommended by TMDB viewers · both documentary
Popcorn FlickMovies like thisTo Kill a Tiger (2023)
Ranjit, a farmer in India, takes on the fight of his life when he demands justice for his 13-year-old daughter, the victim of a brutal gang rape. His decision to support his daughter is virtually unheard of, and his journey unprecedented.
Why it matches: Recommended by TMDB viewers · both documentary
Worth the HypeMovies like this35 Up (1991)
Director Michael Apted revisits the same group of British-born adults after a 7 year wait. The subjects are interviewed as to the changes that have occurred in their lives during the last seven years.
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 thisMemories of a Murderer: The Nilsen Tapes (2021)
Serial killer Dennis Nilsen narrates his life and horrific crimes via a series of chilling audiotapes recorded from his jail cell.
Why it matches: Recommended by TMDB viewers · both documentary
Popcorn FlickMovies like thisDirected by John Ford (1971)
A documentary about the life and films of director John Ford.
Why it matches: Recommended by TMDB viewers · both documentary
Worth the HypeMovies like thisMea Maxima Culpa: Silence in the House of God (2012)
Alex Gibney explores the charged issue of pedophilia in the Catholic Church, following a trail from the first known protest against clerical sexual abuse in the United States and all way to the Vatican.
Why it matches: Recommended by TMDB viewers · both documentary
Worth the HypeMovies like this28 Up (1985)
Just two years away from turning 30, participants in Michael Apted's documentary series are facing serious questions of identity and purpose, wondering whether they've found their place in the world.
Why it matches: Recommended by TMDB viewers · both documentary
Worth the HypeMovies like thisA Toxic Love Story (2026)
A string of threatening emails escalates into a revenge plot involving a newly married US marshal and his ex-girlfriend.
Why it matches: Recommended by TMDB viewers · both documentary
Popcorn FlickMovies like thisNaqoyqatsi (2002)
A visual montage portrait of our contemporary world dominated by globalized technology and violence.
Why it matches: Recommended by TMDB viewers · both documentary
Popcorn FlickMovies 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 thisNobody Speak: Trials of the Free Press (2017)
The courtroom and publicity battles between the superstar wrestler and the notorious website explode in a sensational trial all about the limits of the First Amendment and the new no holds barred nature of celebrity life in an internet dominated society.
Why it matches: Recommended by TMDB viewers · both documentary
Popcorn FlickMovies like this
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Frequently asked questions
What are the best movies like Penthouse: Dear Diary?
The closest matches to Penthouse: Dear Diary are American Boy: A Profile of Steven Prince (1978), McQueen (2018) and 21 Up (1977). Below are 17 more, each with the reason it matches.
What should I watch after Penthouse: Dear Diary?
Start with American Boy: A Profile of Steven Prince (1978), the closest match to Penthouse: Dear Diary.
What is the highest-rated movie like Penthouse: Dear Diary?
Pamela, a love story (2023), rated 7.0/10 by 260 TMDB users.
What is the newest movie like Penthouse: Dear Diary?
A Toxic Love Story (2026) is the most recent release on this list.
Are there English movies like Penthouse: Dear Diary?
Yes: American Boy: A Profile of Steven Prince (1978), McQueen (2018) and 21 Up (1977).
How are movies similar to Penthouse: Dear Diary chosen?
First come films that Trakt’s viewers watch alongside Penthouse: Dear Diary, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.