Movies like My Date with Drew (2005)
The best movies like My Date with Drew (2005) are John Candy: I Like Me (2025), The September Issue (2009) and Whitney (2018). If My Date with Drew hooked you with its documentary, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedMaking Squid Game: The Challenge (2023)8.0/10 from 241 votes
- NewestParadise Morbid (2025)Released 2025
John Candy: I Like Me (2025)
Those who knew iconic funnyman John Candy best share his story, in their own words, through never-before-seen archival footage, imagery, and interviews.
Why it matches: Recommended by TMDB viewers · both documentary
Absolute CinemaMovies like thisThe September Issue (2009)
A documentary chronicling Vogue editor-in-chief Anna Wintour's preparations for the 2007 fall-fashion issue.
Why it matches: Recommended by TMDB viewers · both documentary
Popcorn FlickMovies like thisWhitney (2018)
Examines the life and career of singer Whitney Houston. Features never-before-seen archival footage, exclusive recordings, rare performances and interviews with the people who knew her best.
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 thisDemi Lovato: Simply Complicated (2017)
A personal and intimate look into Demi Lovato's life as not only a regular 25 year old, but also one of the biggest pop stars in the world.
Why it matches: Recommended by TMDB viewers · both documentary
Worth the HypeMovies 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 thisMaking Squid Game: The Challenge (2023)
Go behind the scenes and witness how the "Squid Game"-inspired reality show transformed from a scripted drama to a cutthroat, nail-biting competition.
Why it matches: Recommended by TMDB viewers · both documentary
Absolute CinemaMovies 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 thisSeduced and Abandoned (2013)
SEDUCED AND ABANDONED combines acting legend Alec Baldwin with director James Toback as they lead us on a troublesome and often hilarious journey of raising financing for their next feature film. Moving from director to financier to star actor, the two players provide us with a unique look behind the curtain at the world's biggest and most glamourous film festival, shining a light on the bitter-sweet relationship filmmakers have with Cannes and the film business. Featuring insights from directors Martin Scorsese, 'Bernando Bertolucci' and Roman Polanski; actors Ryan Gosling and Jessica Chastain and a host of film distribution luminaries.
Why it matches: Recommended by TMDB viewers · both documentary
Popcorn FlickMovies like thisScotty and the Secret History of Hollywood (2018)
A deliciously scandalous portrait of unsung Hollywood legend Scotty Bowers, whose bestselling memoir chronicled his decades spent as sexual procurer to the stars.
Why it matches: Recommended by TMDB viewers · both documentary
Popcorn FlickMovies like thisKeith Richards: Under the Influence (2015)
A portrait of Keith Richards that takes us on a journey to discover the genesis of his sound as a songwriter, guitarist and performer.
Why it matches: Recommended by TMDB viewers · both documentary
Popcorn FlickMovies like thisMarvel Studios Assembled: The Making of Eternals (2022)
Join director Chloe Zhao and the Cast of Eternals as they recount their experiences during the making of Marvel Studios’ most ambitious film to date. Discover how the ensemble cast felt stepping into their roles, filming in remote locations, and creating bonds that would help to create the on-screen relationships that span over 7,000 years.
Why it matches: Recommended by TMDB viewers · both documentary
Worth the HypeMovies 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 thisSupersonic (2016)
Supersonic charts the meteoric rise of Oasis from the council estates of Manchester to some of the biggest concerts of all time in just three short years. This palpable, raw and moving film shines a light on one of the most genre and generation-defining British bands that has ever existed and features candid new interviews with Noel and Liam Gallagher, their mother, and members of the band and road crew.
Why it matches: Recommended by TMDB viewers · both documentary
Worth the HypeMovies like thisJoan Didion: The Center Will Not Hold (2017)
Literary icon Joan Didion reflects on her remarkable career and personal struggles in this intimate documentary directed by her nephew, Griffin Dunne.
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 thisLemmy (2010)
Over four decades, Motorhead frontman Lemmy Kilmister has registered an immeasurable impact on music history. Nearly 65, he remains the living embodiment of the rock and roll lifestyle, and this feature-length documentary tells his story, one of a hard-living rock icon who continues to enjoy the life of a man half his age.
Why it matches: Recommended by TMDB viewers · both documentary
Worth the HypeMovies like thisThe Show Must Go On: The Queen + Adam Lambert Story (2019)
A documentary chronicling Queen and Lambert's incredible journey since they first shared the stage together on "American Idol" in 2009.
Why it matches: Recommended by TMDB viewers · both documentary
Worth the HypeMovies like thisObi-Wan Kenobi: A Jedi's Return (2022)
This special explores the return of Obi-Wan Kenobi and Anakin Skywalker to the screen, as well as Ewan McGregor and Hayden Christensen to their classic roles. Director Deborah Chow leads the cast and crew as they create new heroes and villains that live alongside new incarnations of beloved Star Wars characters, and an epic story that dramatically bridges the saga films.
Why it matches: Recommended by TMDB viewers · both documentary
Popcorn FlickMovies like thisThe Class of ‘92 (2013)
A detailing of the rise to prominence and global sporting superstardom of six supremely talented young Manchester United football players (David Beckham, Nicky Butt, Ryan Giggs, Paul Scholes, Phil and Gary Neville). The film covers the period 1992-1999, culminating in Manchester United's European Cup triumph.
Why it matches: Recommended by TMDB viewers · both documentary
Worth the HypeMovies like thisThe Collector (2024)
The offbeat, fairytale story of Wizard of Oz fanatic and obsessive pop culture collector Willard Carroll. From dining with Munchkins to owning the world’s largest private collection of Oz memorabilia, Willard is proof that one story can change the entire trajectory of your life.
Why it matches: Similar story and style · both documentary
Otaku - Children of the Virtual Empire (1994)
A documentary that explores the life styles of various otakus in Japan. Various interviews are given to selected otakus who express how interesting it is to be an otaku as oppose to not being one at all. Along with various shots of various Japanese city landscapes and the inside of an average otaku home from rooms filled with videos, models, and the latest in technology.
Why it matches: Similar story and style · both documentary
Alone (1990)
A documentary-like film about Jussi Parviainen's divorce.
Why it matches: Similar story and style · both documentary
The Art of Evil (2024)
Vae Victis tells about the life story of painter Valerio De Filippis, a man who has made art his way of being in the world but currently in the grip of the dreaded artist's block in view of a very important exhibition.
Why it matches: Similar story and style · both documentary
Grizzly Man (2005)
Follows the story of "Grizzly Man" Timothy Treadwell and what the thirteen summers in a National Park in Alaska were like in his attempt to protect the grizzly bears. The film is full of unique images and a look into the spirit of a man who sacrificed himself for nature.
Why it matches: Similar story and style · both documentary
Worth the HypeMovies like thisNightcrawlers (2019)
For five years, Stephen McCoy documented street life in Boston. This is what he captured.
Why it matches: Similar story and style · both documentary
The Faraway Nearby (2024)
The Faraway Nearby follows the tragic life of pioneer physicist Joseph Weber, whose pursuit of gravitational waves takes him on a dizzying journey from the height of acclaim to the depths of despair and disdain when he breaks the cardinal rule of science and clings to his ideas though his results can't be duplicated. Physicists, artists, and other creatives explore the emotional side of discovery and question whether the risk is worth the journey.
Why it matches: Similar story and style · both documentary
From Dogma to Dogville: Don't Try This at Home (2006)
A documentary with the three cinematographers known for breaking away cinema away from celluloid with the introduction of digital video.
Why it matches: Similar story and style · both documentary
American Movie (1999)
American Movie documents the story of filmmaker Mark Borchardt, his mission, and his dream. Spanning over two years of intense struggle with his film, his family, financial decline, and spiritual crisis, American Movie is a portrayal of ambition, obsession, excess, and one man's quest for the American Dream.
Why it matches: Similar story and style · both documentary
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Frequently asked questions
What are the best movies like My Date with Drew?
The closest matches to My Date with Drew are John Candy: I Like Me (2025), The September Issue (2009) and Whitney (2018). Below are 27 more, each with the reason it matches.
What should I watch after My Date with Drew?
Start with John Candy: I Like Me (2025), the closest match to My Date with Drew.
What is the highest-rated movie like My Date with Drew?
Making Squid Game: The Challenge (2023), rated 8.0/10 by 241 TMDB users.
What is the newest movie like My Date with Drew?
Paradise Morbid (2025) is the most recent release on this list.
Are there English movies like My Date with Drew?
Yes: John Candy: I Like Me (2025), The September Issue (2009) and Whitney (2018).
How are movies similar to My Date with Drew chosen?
First come films that Trakt’s viewers watch alongside My Date with Drew, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.