Movies Like To Leo with Love

If you liked To Leo with Love (1998), a documentary movie directed by J.W. Engwell, 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
Drew: The Man Behind the Poster (2013)
★ 7/10Also documentary
A documentary on legendary movie-poster artist Drew Struzan.
2
As I Was Moving Ahead Occasionally I Saw Brief Glimpses of Beauty (2000)
★ 7.8/10Also documentary
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.
3
28 Up (1985)
★ 7.5/10Also documentary
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.
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
The Class of ‘92 (2013)
★ 7.1/10Also documentary
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)…
6
Directed by John Ford (1971)
★ 7/10Also documentary
A documentary about the life and films of director John Ford.
7
The Summers of It - Chapter Two: It Ends (2019)
★ 7.1/10Also documentary
This documentary focuses on the actors and their journey over two summers to create the remake to the original IT, by Stephen King. The documentary originally released as bonus material, bundled with IT: Chapter Two.
8
Fuck (2006)
★ 6.4/10Also documentary
A documentary on the expletive's origin, why it offends some people so deeply, and what can be gained from its use.
9
S4: The Bob Lazar Story (2026)
★ 8.4/10Also documentary
Over 35 years after Bob Lazar's revelations, this documentary exposes secrets of a facility the government still denies. Featuring Lazar's testimony, recreations, and new evidence, it reopens a case that continues to…
10
Ex Libris: The New York Public Library (2017)
★ 6.4/10Also documentary
A documentary about how a dominant cultural and demographic institution both sustains their traditional activities and adapts to the digital revolution.
11
Elstree 1976 (2015)
★ 6.2/10Also documentary
A documentary about ten very different lives connected by having appeared onscreen wearing masks or helmets in Star Wars.
12
Justin Bieber's Believe (2013)
★ 6.9/10Also documentary
A backstage and on-stage look at Justin Bieber during his rise to super stardom.
13
Above Majestic (2018)
★ 7.4/10Also documentary
A look at the origins, history and conspiracies behind the "Majestic 12", a clandestine group of military and corporate figureheads charged with reverse-engineering extraterrestrial technology.
14
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.
15
Diego Maradona (2019)
★ 7.4/10Also documentary
Constructed from over 500 hours of never-before-seen footage, this documentary centers on the personal life and career of the controversial football player Diego Maradona who played for SSC Napoli and Argentina in the…
16
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…
17
Being Eddie (2025)
★ 6.8/10Also documentary
From teen comedian to Hollywood legend, Eddie Murphy revisits his extraordinary showbiz ride with raw honesty and humor.
18
42 Up (1999)
★ 7.6/10Also documentary
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.
19
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…
20
Love, Antosha (2019)
★ 7.4/10Also documentary
From a prolific career in film and television, Anton Yelchin left an indelible legacy as an actor. Through his journals and other writings, his photography, the original music he wrote, and interviews with his family…