Movies Like Roy's World: Barry Gifford's Chicago

If you liked Roy's World: Barry Gifford's Chicago (2020), a documentary movie directed by Rob Christopher, 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
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.
2
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…
3
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…
4
Directed by John Ford (1971)
★ 7/10Also documentary
A documentary about the life and films of director John Ford.
5
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.
6
Gilbert (2017)
★ 6.7/10Also documentary
The life and career of one of comedy's most inimitable modern voices, Mr. Gilbert Gottfried.
7
My Mom Jayne (2025)
★ 8/10Also documentary
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…
8
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.
9
The U.S. vs. John Lennon (2006)
★ 6.6/10Also documentary
A documentary on the life of John Lennon, with a focus on the time in his life when he transformed from a musician into an antiwar activist.
10
Drew: The Man Behind the Poster (2013)
★ 7/10Also documentary
A documentary on legendary movie-poster artist Drew Struzan.
11
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.
12
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.
13
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.
14
Dawg Fight (2015)
★ 6.4/10Also documentary
In a crime-plagued neighborhood near Miami, brutal, bare-knuckled backyard fights give young men a chance to earn money -- and self-respect.
15
Naqoyqatsi (2002)
★ 6.2/10Also documentary
A visual montage portrait of our contemporary world dominated by globalized technology and violence.
16
One Last Adventure: The Making of Stranger Things 5 (2026)
★ 7.2/10Also documentary
An inside look at the years of effort and craft that went into the final installment of the Duffer Brothers' generation-defining series.
17
Untold: Jake Paul the Problem Child (2023)
★ 5.8/10Also documentary
Pro boxing sensation — and perennial troublemaker — Jake Paul shares his unlikely journey from online prankster to power puncher in this documentary.
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
Selena Gomez: My Mind & Me (2022)
★ 8.4/10Also documentary
After years in the limelight, Selena Gomez achieves unimaginable stardom. But just as she reaches a new peak, an unexpected turn pulls her into darkness. This uniquely raw and intimate documentary spans her six-year…
20
21 Up (1977)
★ 7.4/10Also documentary
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…