Movies Like My Date with Drew

If you liked My Date with Drew (2005), a documentary movie directed by Brett Winn and Jon Gunn, 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
Whitney (2018)
★ 7.3/10Also documentary
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.
2
John Candy: I Like Me (2025)
★ 7.9/10Also documentary
Those who knew iconic funnyman John Candy best share his story, in their own words, through never-before-seen archival footage, imagery, and interviews.
3
I Am Heath Ledger (2017)
★ 7.4/10Also documentary
The life and career of an actor, artist, and icon. His own journey through his own camera.
4
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.
5
Making Squid Game: The Challenge (2023)
★ 8/10Also documentary
Go behind the scenes and witness how the "Squid Game"-inspired reality show transformed from a scripted drama to a cutthroat, nail-biting competition.
6
Seduced and Abandoned (2013)
★ 6.2/10Also documentary
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…
7
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…
8
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…
9
Beyond Infinity: Buzz and the Journey to Lightyear (2022)
★ 7/10Also documentary
Explore the evolution of Buzz Lightyear from toy to human in the making of Pixar’s Lightyear. Dive into the origin and cultural impact of everyone’s favorite Space Ranger, the art of designing a new “human Buzz,” and…
10
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.
11
The Bee Gees: How Can You Mend a Broken Heart (2020)
★ 7.7/10Also documentary
The story of the triumphs and hurdles of brothers Barry, Maurice, and Robin Gibb, otherwise known as the Bee Gees. The iconic trio, who found early fame in the 1960s, went on to write over 1,000 songs and have 20 No. 1…
12
For the Love of Spock (2016)
★ 7.4/10Also documentary
The life of Mr. Spock, as well as that of Leonard Nimoy, the actor who played him for almost fifty years, written and directed by his son: Adam.
13
The AI Doc: Or How I Became an Apocaloptimist (2026)
★ 7/10Also documentary
A father-to-be tries to figure out what is happening with all this AI insanity, and explores the most powerful technology humanity has ever created... and what's at stake if we get it wrong.
14
Marvel Studios Assembled: The Making of Eternals (2022)
★ 7.1/10Also documentary
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…
15
Looking for Richard (1996)
★ 6.8/10Also documentary
Al Pacino's deeply-felt rumination on Shakespeare's significance and relevance to the modern world through interviews and an in-depth analysis of "Richard III."
16
180° South (2010)
★ 7.2/10Also documentary
The film follows adventurer Jeff Johnson as he retraces the epic 1968 journey of his heroes Yvon Chouinard and Doug Tompkins to Patagonia.
17
Obi-Wan Kenobi: A Jedi's Return (2022)
★ 6.8/10Also documentary
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…
18
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…
19
Justin Bieber's Believe (2013)
★ 6.9/10Also documentary
A backstage and on-stage look at Justin Bieber during his rise to super stardom.
20
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…