Movies Like Milk Boy - A film essay

If you liked Milk Boy - A film essay, a documentary and comedy movie directed by Josh Whiteman, 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
Evil Influencer: The Jodi Hildebrandt Story (2025)
★ 6.2/10Also documentary
Unravel the case of Utah therapist Jodi Hildebrandt, whose child abuse arrest with parenting YouTuber Ruby Franke exposed a twisted tale of manipulation.
2
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.
3
American Teen (2008)
★ 6.4/10Also documentary
A documentary on seniors at a high school in a small Indiana town and their various cliques.
4
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.
5
In the Realms of the Unreal (2004)
★ 7.2/10Also documentary
In the Realms of the Unreal is a documentary about the reclusive Chicago-based artist Henry Darger. Henry Darger was so reclusive that when he died his neighbors were surprised to find a 15,145-page manuscript along…
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
Overnight (2003)
★ 6.4/10Also documentary
Alternately hilarious and horrifying, Overnight chronicles one man's misadventures of making a Hollywood movie. It starts out as a rags to riches story as Troy Duffy, a Boston-bred bartender, sells his first screenplay…
8
Looking for Richard (1996)
★ 6.8/10Also documentary
Al Pacino's deeply-felt rumination on Shakespeare's significance and relevance to the modern world through interviews and an in-depth analysis of "Richard III."
9
Roger & Me (1989)
★ 7.1/10Also documentary and comedy
A documentary about the closure of General Motors' plant at Flint, Michigan, which resulted in the loss of 30,000 jobs. Details the attempts of filmmaker Michael Moore to get an interview with GM CEO Roger Smith.
10
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.
11
Aziz Ansari: Right Now (2019)
★ 7.1/10Also comedy and documentary
In a comedy special directed by Spike Jonze, Aziz Ansari shares deep personal insights and hilarious takes on wokeness, family and the social climate.
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
Unknown Number: The High School Catfish (2025)
★ 6.7/10Also documentary
Vulgar, taunting texts blow up the phones of a teen and her boyfriend. Who's sending them — and why? This twisty documentary reveals the shocking answer.
14
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.
15
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…
16
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.
17
56 Up (2012)
★ 7.2/10Also documentary
When a cross-section of seven-year-olds were interviewed for 7 Up in 1964 it was immediately evident that their social backgrounds influenced their attitudes towards life. While the upper class children were confident…
18
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.
19
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.
20
Audrey (2020)
★ 7.1/10Also documentary
An unprecedented and intimate look at the life, work and enduring legacy of British actress Audrey Hepburn (1929-1993).