Movies Like Caddyshack: The 19th Hole

If you liked Caddyshack: The 19th Hole (1999), a documentary and comedy movie directed by Bruce Stuart Greenberg, 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
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.
2
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…
3
The Kid Stays in the Picture (2002)
★ 6.6/10Also documentary
Documentary about legendary Paramount producer Robert Evans, based on his famous 1994 autobiography.
4
Game of Thrones: The Last Watch (2019)
★ 7/10Also documentary
For a year, acclaimed British filmmaker Jeanie Finlay was embedded on the set of the hit HBO series “Game of Thrones,” chronicling the creation of the show’s most ambitious and complicated season. Debuting one week…
5
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.
6
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.
7
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…
8
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.
9
Blue Collar Comedy Tour: The Movie (2003)
★ 6/10Also comedy and documentary
The comedic stylings of four sort-of famous funnymen are brought to the big screen courtesy of this 2002 documentary.
10
Jackass 3D (2010)
★ 6.6/10Also comedy and documentary
Johnny Knoxville, Bam Margera, Steve-O, Wee Man and the rest of their fearless and foolhardy friends take part in another round of outrageous pranks and stunts. In addition to standing in the path of a charging bull…
11
Electric Boogaloo: The Wild, Untold Story of Cannon Films (2014)
★ 7.2/10Also documentary
A documentary about the rise and fall of the Cannon Film Group, the legendary independent film company helmed by Israeli cousins Menahem Golan and Yoram Globus.
12
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.
13
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.
14
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.
15
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.
16
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.
17
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.
18
Jackass: The Movie (2002)
★ 6.3/10Also comedy and documentary
Johnny Knoxville and his band of maniacs perform a variety of stunts and gross-out gags on the big screen for the first time. They wander around Japan in panda outfits, wreak havoc on a once civilized golf course, they…
19
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.
20
Jackass Forever (2022)
★ 6.8/10Also comedy and documentary
The Jackass crew, along with some newcomers, returns for one more round of hilarious, absurd, and dangerous stunts.