Movies Like How to Live with Regret

If you liked How to Live with Regret (2018), a documentary and comedy movie directed by John Wilson, 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
American Pie: Revealed (2004)
★ 6/10Also documentary and comedy
Documentary about the making of American Pie (1999), American Pie 2 (2001) and American Wedding (2003).
2
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.
3
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.
4
Trevor Noah: You Laugh But It's True (2011)
★ 6.7/10Also documentary and comedy
In the world of stand-up comedy in South Africa, Trevor Noah uses his childhood experiences in a biracial family during apartheid to prepare for his first one-man show.
5
Sherman's March (1986)
★ 6.3/10Also documentary
Documentarian Ross McElwee originally set out to make a travelogue of sorts tracing General William T. Sherman's infamous scorched-earth march through the Confederacy in the latter stages of the Civil War. Instead…
6
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.
7
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.
8
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…
9
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.
10
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…
11
The Amazing Johnathan Documentary (2019)
★ 6.1/10Also documentary and comedy
What begins as a documentary following the final tour of a dying magician - "The Amazing Johnathan" - becomes an unexpected and increasingly bizarre journey as the filmmaker struggles to separate truth from illusion.
12
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.
13
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.
14
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.
15
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…
16
Jackass Presents: Bad Grandpa .5 (2014)
★ 6/10Also comedy and documentary
Bad Grandpa .5 gives you a whole new perspective on the world of Irving Zisman with bonus scenes and pranks also featuring Spike Jonze as "Gloria" and Catherine Keener as Irving's wife "Ellie", plus a look at the…
17
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.
18
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."
19
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.
20
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.