Movies Like Jonathan Winters: Rare & Riotous

If you liked Jonathan Winters: Rare & Riotous (2005), 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
Man on the Moon (1999)
★ 7.2/10
The story of the life and career of eccentric avant-garde comedian, Andy Kaufman.
2
Broadway Danny Rose (1984)
★ 7.1/10
A hapless talent manager named Danny Rose, by helping a client, gets dragged into a love triangle involving the mob. His story is told in flashback, an anecdote shared amongst a group of comedians over lunch at New…
3
Whitney Cummings: Can I Touch It? (2019)
★ 6.7/10
In her fourth stand-up special, Whitney Cummings returns to her hometown of Washington, D.C., and riffs on modern feminism, technology and more.
4
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…
5
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…
6
A Hard Day's Night (1964)
★ 7.3/10
Capturing John Lennon, Paul McCartney, George Harrison and Ringo Starr in their electrifying element, 'A Hard Day's Night' is a wildly irreverent journey through this pastiche of a day in the life of The Beatles during…
7
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.
8
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…
9
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.
10
Saturday Night Live: The Best of Will Ferrell (2002)
★ 7.8/10
The best skits from Will Ferrell's days on Saturday Night Live 1995-2002
11
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.
12
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.
13
Being Eddie (2025)
★ 6.8/10
From teen comedian to Hollywood legend, Eddie Murphy revisits his extraordinary showbiz ride with raw honesty and humor.
14
Let's Make Love (1960)
★ 6.4/10
When billionaire Jean-Marc Clement learns that he is to be satirized in an off-Broadway revue, he passes himself off as an actor playing him in order to get closer to the beautiful star of the show, Amanda Dell.
15
Robin Williams: Come Inside My Mind (2018)
★ 7.9/10
A funny, intimate and heartbreaking portrait of one of the world’s most beloved and inventive comedians, Robin Williams, told largely through his own words. Celebrates what he brought to comedy and to the culture at…
16
Hot Shots! (1991)
★ 6.6/10
The gang that created Airplane! and The Naked Gun sets its sights on Top Gun in this spoof. Topper Harley is a talented but unstable fighter pilot with an axe to grind: clearing the family name. His mission is to…
17
Annie Hall (1977)
★ 7.7/10
New York comedian Alvy Singer falls in love with the ditsy Annie Hall.
18
Lucy and Desi (2022)
★ 7.1/10
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.
19
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.
20
Someone Like You... (2001)
★ 6/10
Jane Goodale has everything going for her. She's a producer on a popular daytime talk show, and is in a hot romance with the show's dashing executive producer Ray. But when the relationship goes terribly awry, Jane…