Movies Like Portrait of Leonardo: The Kid Who Took Hollywood

If you liked Portrait of Leonardo: The Kid Who Took Hollywood (1998), a documentary movie directed by Chris Case, 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
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.
2
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.
3
Directed by John Ford (1971)
★ 7/10Also documentary
A documentary about the life and films of director John Ford.
4
Casting By (2012)
★ 6.9/10Also documentary
This essential new documentary pays tribute to the legacy of the late, legendary casting director Marion Dougherty and shines a light on one of the most overlooked and least understood crafts in filmmaking.
5
Sidney (2022)
★ 6.9/10Also documentary
This revealing documentary honors the legendary Sidney Poitier—iconic actor, filmmaker, and civil rights activist. Featuring interviews with Denzel Washington, Spike Lee, Halle Berry, and more.
6
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.
7
Justin Bieber's Believe (2013)
★ 6.9/10Also documentary
A backstage and on-stage look at Justin Bieber during his rise to super stardom.
8
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.
9
The Curious Birth of Benjamin Button (2009)
★ 7/10Also documentary
A documentary about the making of David Fincher's 2008 film THE CURIOUS CASE OF BENJAMIN BUTTON. Virtually every element in the evolution of the Fincher's film is documented here, from the project's attachment to…
10
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…
11
A Decade Under the Influence (2003)
★ 7.9/10Also documentary
A documentary examining the decade of the 1970s as a turning point in American cinema. Some of today's best filmmakers interview the influential directors of that time.
12
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)…
13
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.
14
A Toxic Love Story (2026)
★ 6.4/10Also documentary
A string of threatening emails escalates into a revenge plot involving a newly married US marshal and his ex-girlfriend.
15
Charlie: The Life and Art of Charles Chaplin (2003)
★ 7/10Also documentary
Brilliant, long in-the-works story of the life and art of the world's greatest comedian and the cinema's first genius, Charlie Chaplin. Produced, written and directed by renowned film critic Richard Schickel.
16
Come See Me in the Good Light (2025)
★ 7.1/10Also documentary
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.
17
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.
18
Drew: The Man Behind the Poster (2013)
★ 7/10Also documentary
A documentary on legendary movie-poster artist Drew Struzan.
19
35 Up (1991)
★ 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.
20
McQueen (2018)
★ 7.4/10Also documentary
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…