Movies like Caddyshack: The 19th Hole (1999)
The best movies like Caddyshack: The 19th Hole (1999) are Windy City Heat (2003), Blue Collar Comedy Tour: The Movie (2003) and The Aristocrats (2005). If Caddyshack: The 19th Hole hooked you with its documentary and comedy, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedRoger & Me (1989)7.1/10 from 329 votes
- NewestBlood Sugar (2026)Released 2026
Windy City Heat (2003)
A man caught up in the glamor of being a Hollywood celebrity has no idea that the production he's in is a fake.
Why it matches: Recommended by TMDB viewers · both comedy & documentary
Worth the HypeMovies like thisBlue Collar Comedy Tour: The Movie (2003)
The comedic stylings of four sort-of famous funnymen are brought to the big screen courtesy of this 2002 documentary.
Why it matches: Recommended by TMDB viewers · both comedy & documentary
Popcorn FlickMovies like thisThe Aristocrats (2005)
One hundred superstar comedians tell the same very, VERY dirty, filthy joke--one shared privately by comics since Vaudeville.
Why it matches: Recommended by TMDB viewers · both comedy & documentary
SnoozefestMovies like thisTrevor Noah: You Laugh But It's True (2011)
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.
Why it matches: Recommended by TMDB viewers · both documentary & comedy
Popcorn FlickMovies like thisJackass Presents: Bad Grandpa .5 (2014)
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 evolution of Johnny Knoxville's naughty alter-ego, the makeup effects, and a behind-the-scenes peek at the idiocy it takes to make a hidden camera movie in public.
Why it matches: Recommended by TMDB viewers · both comedy & documentary
Popcorn FlickMovies like thisKevin Hart: What Now? (2016)
Comedian Kevin Hart performs in front of a crowd of 50,000 people at Philadelphia's outdoor venue, Lincoln Financial Field.
Why it matches: Recommended by TMDB viewers · both comedy & documentary
Popcorn FlickMovies like thisRoger & Me (1989)
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.
Why it matches: Recommended by TMDB viewers · both documentary & comedy
Worth the HypeMovies like thisThe Amazing Johnathan Documentary (2019)
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.
Why it matches: Recommended by TMDB viewers · both documentary & comedy
Popcorn FlickMovies like thisJackass 3D (2010)
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, launching themselves into the air and crashing through various objects, the guys perform in segments such as "Sweatsuit Cocktail," "Beehive Tetherball" and "Lamborghini Tooth Pull."
Why it matches: Recommended by TMDB viewers · both comedy & documentary
Popcorn FlickMovies like thisAnthony Jeselnik: Fire in the Maternity Ward (2019)
Forging his own comedic boundaries, Anthony Jeselnik revels in getting away with saying things others can't in this stand-up special shot in New York.
Why it matches: Recommended by TMDB viewers · both comedy & documentary
Worth the HypeMovies like thisFuck (2006)
A documentary on the expletive's origin, why it offends some people so deeply, and what can be gained from its use.
Why it matches: Recommended by TMDB viewers · both documentary
Popcorn FlickMovies like thisElectric Boogaloo: The Wild, Untold Story of Cannon Films (2014)
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.
Why it matches: Recommended by TMDB viewers · both documentary
Worth the HypeMovies like thisHurricane of Fun: The Making of Wet Hot (2015)
Exclusive behind-the-scenes footage offers a glimpse into the comic minds behind a "Wet Hot" summer-camp cult hit featuring many future stars.
Why it matches: Recommended by TMDB viewers · both documentary
Popcorn FlickMovies like thisGame of Thrones: The Last Watch (2019)
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 after the series 8 finale, GAME OF THRONES: THE LAST WATCH delves deep into the mud and blood to reveal the tears and triumphs involved in the challenge of bringing the fantasy world of Westeros to life in the very real studios, fields and car-parks of Northern Ireland. Made with unprecedented access, GAME OF THRONES: THE LAST WATCH is an up-close and personal portrait from the trenches of production, following the crew and the cast as they contend with extreme weather, punishing deadlines and an ever-excited fandom hungry for spoilers. Much more than a “making of” documentary, this is a funny, heartbreaking story, told with wit and intimacy, about the bittersweet pleasures of what it means to create a world – and then have to say goodbye to it.
Why it matches: Recommended by TMDB viewers · both documentary
Worth the HypeMovies like thisThe Kid Stays in the Picture (2002)
Documentary about legendary Paramount producer Robert Evans, based on his famous 1994 autobiography.
Why it matches: Recommended by TMDB viewers · both documentary
Popcorn FlickMovies like thisEvil Influencer: The Jodi Hildebrandt Story (2025)
Unravel the case of Utah therapist Jodi Hildebrandt, whose child abuse arrest with parenting YouTuber Ruby Franke exposed a twisted tale of manipulation.
Why it matches: Recommended by TMDB viewers · both documentary
Popcorn FlickMovies like thisWick Is Pain (2025)
Witness the never-before-seen footage and true story behind the John Wick phenomenon – from independent film to billion-dollar franchise.
Why it matches: Recommended by TMDB viewers · both documentary
Worth the HypeMovies like thisJackie Chan: My Story (1998)
Jackie Chan is one of the world's biggest action stars, famed for his wacky sense of humor, remarkable martial arts techniques, and willingness to perform incredible stunts without the use of doubles -- or a net. This video takes a personal look at Chan as he works on screen projects in Hollywood and Beijing and candidly discusses his life and work.
Why it matches: Recommended by TMDB viewers · both documentary
Popcorn FlickMovies like thisLove, Antosha (2019)
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, friends, and colleagues, this film looks not just at Anton's impressive career, but at a broader portrait of the man.
Why it matches: Recommended by TMDB viewers · both documentary
Worth the HypeMovies like thisConan O'Brien Can't Stop (2011)
A documentary that follows the former Tonight Show host. Filmed during Conan’s ”Legally Prohibited From Being Funny on Television” comedy tour, after his departure from the Tonight Show, taking viewers on an intimate journey of O’Brien’s life.
Why it matches: Recommended by TMDB viewers · both documentary
Popcorn FlickMovies like thisExploring the Set of 'Moonrise Kingdom' (2015)
Martin Scali, who was Wes Anderson's assistant on "Fantastic Mr. Fox", shot this short documentary in Newport, Rhode Island, during the filming of "Moonrise Kingdom".
Why it matches: Similar story and style · both documentary & comedy
Farce of the Penguins (2006)
In this spoof of "March of the Penguins," nature footage of penguins near the South Pole gets a soundtrack of human voices. Carl and Jimmy, best friends, walk 70 miles to the mating grounds where the female penguins wait. The huddled masses of females - especially Melissa and Vicki - talk about males, mating, and what might happen this year. Carl, Jimmy, and the other males make the long trek talking about food, fornication and flatulence. Until this year, Carl's sex life has been dismal, but he falls hard for Melissa. She seems to like him. A crisis develops when Jimmy comes upon something soft in the dark. Can friends forgive? Does parenthood await Carl and Melissa?
Why it matches: Similar story and style · both comedy & documentary
SnoozefestMovies like thisLint: The Movie (2011)
Documents the life and work of cult SF author and philosopher Jeff Lint, creator of some of the strangest and most inventive works of the 20th century. Featuring clips from Lint's books, cartoons, music, comics and films, the movie follows Lint's life from the days of vintage pulp, psychedelia and his disastrous scripts for Star Trek and Patton. Newly discovered archive footage and recordings of Lint himself, and commentary by those who knew and read him, results in a compelling portrait of the creator of Clowns and Insects, Jelly Result, The Stupid Conversation, the Caterer comic, and Catty and the Major, the scariest kids' cartoon ever aired.
Why it matches: Similar story and style · both documentary & comedy
Back On Crack | The Cracked Tiles Documentary (2024)
In the mid 1990's Mr. Ball managed a band called The Cracked Tiles. Thanks to his Certificate III in Business (Administration) and his superior intuitive powers, Mr. Ball acquired the rights to their album 'Hi-Vis Factory'. Due to various circumstances, which Mr. Ball would rather not comment on, the album was never released. As a last ditch attempt to make some money he is now releasing it after 25-30 years, no one seems to be sure on the maths for some reason. Probably because we don't know when it will actually come out.
Why it matches: Similar story and style · both comedy
My Beautiful Laundrette (1985)
A young Pakistani Briton manages a rundown laundrette with his lover while dealing with tension in his family, the local Pakistani community, and a persistent mob of skinheads.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisMaking 1899 (2022)
Go behind the scenes and see how the creators of "Dark" used groundbreaking virtual technology "The Volume" to shoot their new mystery series.
Why it matches: Similar story and style · both documentary
Blood Sugar (2026)
Desperate to reinstate himself as cinema's top vampire, Dracula sells his castle to finance a vanity project that stars his roomate, a popular vampire influencer named Ishmael.
Why it matches: Similar story and style · both comedy
Helena from the Wedding: Cast Interviews (2011)
On-set interviews with the cast of Helena from the Wedding (2010).
Why it matches: Similar story and style · both documentary
Paradise Falls (2011)
The whole film was created in 48 hours as part of the "48 Hour Film Project - Dubai" competition. With his debut work 'The Bridge of Time' spending seven weeks on the New York Times Bestseller list, Karim Mushtak was once hailed as the most promising Arab novelist of his generation. And then he disappeared from the public eye. A group of filmmakers find him in a run down residential compound where he is the last remaining tenant, refusing to move out as he tries to complete perhaps the most difficult of all second novels.
Why it matches: Similar story and style · both comedy
My secretary is mad... mad... mad... (1967)
The aviation company for which Ricardo works gives a secretary a trip to Peru.
Why it matches: Similar story and style · both comedy
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Frequently asked questions
What are the best movies like Caddyshack: The 19th Hole?
The closest matches to Caddyshack: The 19th Hole are Windy City Heat (2003), Blue Collar Comedy Tour: The Movie (2003) and The Aristocrats (2005). Below are 27 more, each with the reason it matches.
What should I watch after Caddyshack: The 19th Hole?
Start with Windy City Heat (2003), the closest match to Caddyshack: The 19th Hole.
What is the highest-rated movie like Caddyshack: The 19th Hole?
Roger & Me (1989), rated 7.1/10 by 329 TMDB users.
What is the newest movie like Caddyshack: The 19th Hole?
Blood Sugar (2026) is the most recent release on this list.
Are there English movies like Caddyshack: The 19th Hole?
Yes: Windy City Heat (2003), Blue Collar Comedy Tour: The Movie (2003) and The Aristocrats (2005).
How are movies similar to Caddyshack: The 19th Hole chosen?
First come films that Trakt’s viewers watch alongside Caddyshack: The 19th Hole, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.