Movies Like When Chicago Was Hollywood

If you liked When Chicago Was Hollywood (1964), a documentary and tv movie movie directed by Tony Verdi, 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
The Godfather Family: A Look Inside (1990)
★ 7.8/10Also documentary and tv movie
A documentary on the making of the three Godfather films, with interviews and recollections from the film makers and cast. This feature also includes the original screen tests of some of the actors for "The Godfather"…
2
Louis Theroux: Twilight of the Porn Stars (2012)
★ 6.3/10Also documentary and tv movie
In 1997, Louis Theroux made a documentary about the world of male porn performers in Los Angeles. 15 years later, he returns to find a business struggling with the deluge of free porn on the internet. Louis revisits…
3
Directed by John Ford (1971)
★ 7/10Also documentary
A documentary about the life and films of director John Ford.
4
No Half Measures: Creating the Final Season of Breaking Bad (2013)
★ 8.5/10Also documentary
A documentary about the making of season five of the acclaimed AMC series Breaking Bad.
5
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.
6
Making Waves: The Art of Cinematic Sound (2019)
★ 6.9/10Also documentary
The history of cinematic sound, told by legendary sound designers and visionary filmmakers.
7
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.
8
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.
9
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.
10
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.
11
Louis Theroux: Louis and the Nazis (2003)
★ 7.2/10Also documentary and tv movie
Louis Theroux travels to California to meet the man dubbed "the most dangerous racist in America"; Tom Metzger. Louis meets him, his family and his publicity manager as well as following him to skinhead rallies and on…
12
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…
13
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.
14
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.
15
The Making of Star Wars (1977)
★ 7.1/10Also documentary and tv movie
Learn the incredible behind-the-scenes story of how the original Star Wars movie was brought to the big screen in this fascinating documentary hosted by C-3PO and R2-D2 which includes interviews with George Lucas and…
16
Making The Witcher (2020)
★ 7.1/10Also documentary and tv movie
Journey into the extraordinary world of "The Witcher" — from casting the roles to Jaskier's catchy song — in this behind-the-scenes look at the series.
17
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…
18
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…
19
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.
20
4 Little Girls (1997)
★ 7.1/10Also documentary and tv movie
On September 15, 1963, a bomb destroyed a black church in Birmingham, Alabama, killing four young girls who were there for Sunday school. It was a crime that shocked the nation--and a defining moment in the history of…