Movies Like Chester P for Mayor: Hip-Hop, Homelessness and the Housing Crisis

If you liked Chester P for Mayor: Hip-Hop, Homelessness and the Housing Crisis (2015), a documentary movie directed by Greg Hall, 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
49 Up (2006)
★ 7.4/10Also documentary
49 Up is the seventh film in a series of landmark documentaries that began 42 years ago when UK-based Granada's World in Action team, inspired by the Jesuit maxim "Give me the child until he is seven and I will give…
2
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.
3
Harmontown (2014)
★ 6.6/10Also documentary
A comedic, brutally honest documentary following self-destructive TV writer Dan Harmon as he takes his live podcast on a national tour.
4
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.
5
Biggie & Tupac (2002)
★ 6.4/10Also documentary
In 1997, rap superstars Tupac Shakur and Christopher Wallace (aka Biggie Smalls, The Notorious B.I.G.) were gunned down in separate incidents, the apparent victims of hip hop's infamous east-west rivalry. Nick…
6
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…
7
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…
8
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.
9
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.
10
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…
11
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.
12
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…
13
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.
14
Oasis: Don't Look Back in Anger (2026)
★ 6.9/10Also documentary
Experience the meteoric rise of Oasis through rare footage and untold stories as the band reunites for Oasis Live '25, chronicling their journey from Manchester streets to global rock stardom.
15
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…
16
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.
17
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…
18
Chris Brown: Welcome to My Life (2017)
★ 6.4/10Also documentary
This compelling Documentary moves beyond the spotlight and past the attention-grabbing headlines to give pop superstar Chris Brown a chance to tell his own story. New interviews with the international phenomenon reveal…
19
The Greatest Night in Pop (2024)
★ 7.9/10Also documentary
On a January night in 1985, music's biggest stars gathered to record "We Are the World." This documentary goes behind the scenes of the historic event.
20
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.