Movies Like Python at 50: Silly Talks and Holy Grails

If you liked Python at 50: Silly Talks and Holy Grails (2019), a documentary and comedy movie, 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 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.
2
Talking Funny (2011)
★ 7.4/10Also comedy and documentary
What does it mean to be a successful comedian? How far can the boundaries of taste be pushed to get a laugh? Four top comics, Ricky Gervais, Louis C.K., Jerry Seinfeld and Chris Rock, discuss and debate their craft.
3
Good Hair (2009)
★ 6.5/10Also documentary and comedy
An exposé of comic proportions that only Chris Rock could pull off, GOOD HAIR visits beauty salons and hairstyling battles, scientific laboratories and Indian temples to explore the way hairstyles impact the…
4
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.
5
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.
6
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).
7
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.
8
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…
9
The Aristocrats (2005)
★ 5.9/10Also comedy and documentary
One hundred superstar comedians tell the same very, VERY dirty, filthy joke--one shared privately by comics since Vaudeville.
10
Lucy and Desi (2022)
★ 7.1/10Also documentary
Explore the unlikely partnership and enduring legacy of one of the most prolific power couples in entertainment history. Lucille Ball and Desi Arnaz risked everything to be together.
11
Jackass: The Lost Tapes (2009)
★ 6.4/10Also comedy and documentary
The deleted scenes and additional stunts and sketches that originally were not presented in the original series.
12
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…
13
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.
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
An Evening with Kevin Smith (2002)
★ 7.4/10Also comedy and documentary
Kevin Smith interacts in Q&A sessions throughout various college stops in the USA.
16
Patton Oswalt: Talking for Clapping (2016)
★ 6.7/10Also comedy and documentary
Patton Oswalt delivers a fresh hour plus of stand-up, covering everything from misery to defeat to hopelessness. It's his most upbeat special to date.
17
John Candy: I Like Me (2025)
★ 7.9/10Also documentary
Those who knew iconic funnyman John Candy best share his story, in their own words, through never-before-seen archival footage, imagery, and interviews.
18
Love, Antosha (2019)
★ 7.4/10Also documentary
From a prolific career in film and television, Anton Yelchin left an indelible legacy as an actor. Through his journals and other writings, his photography, the original music he wrote, and interviews with his family…
19
Comedy Central Roast of Pamela Anderson (2005)
★ 6.6/10Also comedy and documentary
Comedy Central's best roasters and stand up comedians take a whack at actor/model Pamela Anderson.
20
Being Eddie (2025)
★ 6.8/10Also documentary
From teen comedian to Hollywood legend, Eddie Murphy revisits his extraordinary showbiz ride with raw honesty and humor.