Movies Like Jack Dee - The Best of Jack Dee's Happy Hour

If you liked Jack Dee - The Best of Jack Dee's Happy Hour (2000), a 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
Bo Burnham: Make Happy (2016)
★ 8/10
Combining his trademark wit and self-deprecating humor with original music, Bo Burnham offers up his unique twist on life in this stand-up special about life, death, sexuality, hypocrisy, mental illness and Pringles…
2
Jim Jefferies: This Is Me Now (2018)
★ 7/10
The gleefully irreverent Jefferies skewers “grabby” celebrities, political hypocrisy and his own ill-advised career moves in a brash stand-up special.
3
The Aristocrats (2005)
★ 5.9/10
One hundred superstar comedians tell the same very, VERY dirty, filthy joke--one shared privately by comics since Vaudeville.
4
Larry David: Curb Your Enthusiasm (1999)
★ 7.5/10
Mock documentary about Seinfeld writer Larry David featuring contributions from his friends and colleagues. Larry makes a return to stand-up comedy and prepares to film a television special for HBO. This is the…
5
Monty Python's The Meaning of Life (1983)
★ 7.3/10
Life's questions are 'answered' in a series of outrageous vignettes, beginning with a staid London insurance company which transforms before our eyes into a pirate ship. Then there's the National Health doctors who try…
6
Dave Chappelle: The Dreamer (2023)
★ 6.9/10
From his onstage tackle to the slap heard round the world, Dave Chappelle lets loose in this freewheeling and unfiltered stand-up comedy special.
7
Popstar: Never Stop Never Stopping (2016)
★ 6.6/10
When his new album fails to sell records, pop/rap superstar Conner4real goes into a major tailspin and watches his celebrity high life begin to collapse. He'll try anything to bounce back, anything except reuniting…
8
Adam Sandler: Love You (2024)
★ 6.3/10
Adam Sandler hits the stage for a thrillingly unpredictable comedy special featuring songs, jokes, party-crashing dogs and plenty of love.
9
Sarah Silverman: A Speck of Dust (2017)
★ 6.8/10
In her first comedy special post-health scare, Sarah Silverman shares a mix of fun facts, sad truths and yeah-she-just-went-there moments.
10
Adam Sandler: 100% Fresh (2018)
★ 7.1/10
Adam Sandler takes his comical musical musings back out on the road, from comedy clubs to concert halls to one very unsuspecting subway station.
11
21 & Over (2013)
★ 5.8/10
Brilliant student Jeff Chang has the most important interview of his life tomorrow. But today is still his birthday, what starts off as a casual celebration with friends evolves into a night of debauchery that risks to…
12
Monty Python Live at the Hollywood Bowl (1982)
★ 7.4/10
Monty Python perform many of their greatest sketches at the Hollywood Bowl, including several from pre-Python days.
13
Office Romance (2026)
★ 6.4/10
Jackie, President and CEO of Air Cruz, runs a tight ship in her business, including a rigid anti-fraternization policy for all her employees. When a new sexy lawyer begins working for her, that policy becomes very…
14
Fear of a Black Hat (1994)
★ 6.2/10
Chronicling the controversial career of bad boys N.W.H. (Niggaz With Hats), this uproarious 'mockumentary' lampoons all of hardcore rap's hot-button issues. This underground laugh riot recounts the rise, fall and…
15
David Brent: Life on the Road (2016)
★ 6.1/10
A camera crew catches up with David Brent, the former star of the fictional British series, "The Office" as he now fancies himself a rockstar on the road.
16
Norm Macdonald: Nothing Special (2022)
★ 6.6/10
In his final comedy special, Norm Macdonald ponders casinos, cannibalism, living wills and why you have to be ready for whatever life throws your way.
17
Super Troopers 2 (2018)
★ 5.9/10
When an international border dispute arises between the U.S. and Canada, the Super Troopers- Mac, Thorny, Foster, Rabbit and Farva, are called in to set up a new Highway Patrol station in the disputed area.
18
Mr. & Mrs. Smith (1941)
★ 5.9/10
Happily married for three years, Ann and David Smith live in New York. One morning Ann asks David if he had to do it over again, would he marry her? To her shock, he answers, "No". Later that day, they separately…
19
Eddie Murphy Raw (1987)
★ 7.2/10
Eddie Murphy delights, shocks and entertains with dead-on celebrity impersonations, observations on '80s love, sex and marriage, a remembrance of Mom's hamburgers and much more.
20
Bill Burr: Drop Dead Years (2025)
★ 7.2/10
In what might be his most personal and introspective hour yet, Bill offers hilarious takes on everything from male sadness to dating advice.