Movies Like Whiskey 2: The Adventures of Boozy the Clown

If you liked Whiskey 2: The Adventures of Boozy the Clown (1996), 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
Jackass: Best and Last (2026)
★ 7.3/10Also comedy and documentary
The fifth and final installment to Jackass franchise where the crew go on one last insane crusade.
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
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.
4
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.
5
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."
6
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.
7
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…
8
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.
9
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.
10
Comedy Central Roast of David Hasselhoff (2010)
★ 6.8/10Also comedy and documentary
Time to hassle the Hoff at the rudest, raunchiest television event of the year--The Comedy Central Roast of David Hasselhoff. From running in slo-mo on the beach to inspiring Germany with the power of cheesy pop--it's…
11
Kevin Hart: What Now? (2016)
★ 6.5/10Also comedy and documentary
Comedian Kevin Hart performs in front of a crowd of 50,000 people at Philadelphia's outdoor venue, Lincoln Financial Field.
12
Nitro Circus: The Movie (2012)
★ 6.4/10Also comedy and documentary
You will see Travis Pastrana and the whole Nitro Circus crew perform some of the most ridiculous, awe-inspiring, and simply insane stunts ever caught on camera. Coming to you in three dimensional glory, it will feel…
13
American Movie (1999)
★ 7.5/10Also documentary and comedy
American Movie documents the story of filmmaker Mark Borchardt, his mission, and his dream. Spanning over two years of intense struggle with his film, his family, financial decline, and spiritual crisis, American Movie…
14
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…
15
Lionel Messi: Destiny (2023)
★ 7.8/10Also documentary
Behind-the-scenes documentary about how Lionel Messi succeeded in lifting the World Cup – the only trophy to have eluded him in an incredible career.
16
Richard Pryor: Here and Now (1983)
★ 6.7/10Also comedy and documentary
One of comedian Richard Pryor's later stand-up performances. As foul-mouthed as ever, Pryor touches on most of the same topics as in his previous live shows. Filmed at the Saenger Theatre in New Orleans.
17
Robin Williams: Live on Broadway (2002)
★ 7.8/10Also comedy and documentary
2002 HBO Stand-up Special starring Robin Williams. Recorded and broadcast live from New York City's Broadway Theater at the culmination of his historic 2002 sold-out tour, this special finds the Oscar-winning…
18
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.
19
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.
20
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.