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The Best Jonathan Winters Movies 

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Updated June 11, 2019 196 votes 58 voters 5.9k views 35 items

List Rules Vote for your favorite movies, regardless of critic reviews or how big the role was.

List of the best Jonathan Winters movies, ranked best to worst with movie trailers when available. Jonathan Winters's highest grossing movies have received a lot of accolades over the years, earning millions upon millions around the world. The order of these top Jonathan Winters movies is decided by how many votes they receive, so only highly rated Jonathan Winters movies will be at the top of the list. Jonathan Winters has been in a lot of films, so people often debate each other over what the greatest Jonathan Winters movie of all time is. If you and a friend are arguing about this then use this list of the most entertaining Jonathan Winters films to end the squabble once and for all.

If you think the best Jonathan Winters role isn't at the top, then upvote it so it has the chance to become number one. The greatest Jonathan Winters performances didn't necessarily come from the best movies, but in most cases they go hand in hand.

The Shadow and It's a Mad, Mad, Mad, Mad World are a great starting point for your to rank your favorites on this list

"This list answers the questions, "What are the best Jonathan Winters movies?" and "What are the greatest Jonathan Winters roles of all time?"

Brian Levant and Raja Gosnell both worked with Jonathan Winters over the years, as have plenty of other well-known directors.

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1
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Mickey Rooney, Spencer Tracy, Buster Keaton

Released: 1963

Directed by: Stanley Kramer

It's a Mad, Mad, Mad, Mad World is a 1963 American epic comedy film produced and directed by Stanley Kramer and starring Spencer Tracy with an all-star cast, about the madcap pursuit of $350,000 ...more

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#745 of 1,699 The Most Rewatchable Movies #69 of 1,030 The All-Time Greatest Comedy Filmslisted on Every Oscar Winning Film Ever

2
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Carl Reiner, Alan Arkin, Eva Marie Saint

Released: 1966

Directed by: Norman Jewison

The Russians Are Coming, the Russians Are Coming is a 1966 American comedy film directed by Norman Jewison. It is based on the Nathaniel Benchley novel The Off-Islanders, and was adapted for the ...more

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#232 of 375 The 50+ Best War Movies Ever Made, Ranked #798 of 1,030 The All-Time Greatest Comedy Films #401 of 1,209 The Absolute Funniest Movies Of All Time

3
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James Coburn, Milton Berle, John Gielgud

Released: 1965

Directed by: Tony Richardson

The Loved One is a 1965 black and white comedy film about a business in Los Angeles, which is based on The Loved One: An Anglo-American Tragedy, a short satirical novel by Evelyn Waugh. It was ...more
4
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Halle Berry, Elizabeth Taylor, Rosie O'Donnell

Released: 1994

Directed by: Brian Levant

The Flintstones is a 1994 American buddy comedy film directed by Brian Levant and written by Tom S. Parker, Jim Jennewein and Steven E. de Souza. A live-action adaptation of the 1960s animated ...more

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#9 of 24 Movies You Loved As a Child That Just Don't Hold Up #168 of 302 The Greatest Soundtracks of All Time #54 of 141 The Most Rewatchable Comedy Movies

5
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Peter Ustinov, Jonathan Winters, Keenan Wynn

Released: 1969

Directed by: Jerry Paris

Viva Max! is a 1969 comedy film starring Peter Ustinov, Jonathan Winters and John Astin, directed by Jerry Paris. The film was written by Elliott Baker and based on a 1966 novel by Jim Lehrer.
6
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Sean Connery, Matthew Broderick, Toni Collette

Released: 1993

Directed by: Richard Williams

This film is a British animated fantasy film directed, co-written and co-produced by Canadian animator Richard Williams. The film is famous for its animation and its long, troubled history. It ...more

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#189 of 601 The Best Animated Films Ever #455 of 493 The Funniest '90s Movies #382 of 388 The Best Movies to Watch While Stoned

7
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Dana Delany, Richard Dreyfuss, Jonathan Winters

Released: 1988

Directed by: Paul Mazursky

Moon over Parador is a 1988 romantic comedy film, starring Richard Dreyfuss, Raúl Juliá and Sonia Braga. It is a remake of the 1939 film The Magnificent Fraud, based on the ...more
8
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Jonathan Winters, Danny Cooksey, Frank Welker

Released: 1992

Directed by: Alfred Gimeno, Barry Caldwell, Kent Butterworth, Ken Boyer, Rich Arons, + more

Tiny Toon Adventures: How I Spent My Vacation is a 1992 American direct-to-video animated film from Warner Bros. Animation and Amblin Entertainment. Plans for the film began as early as 1990 and ...more
9
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Stella Stevens, Jonathan Winters, Harvey Korman

Released: 1986

Directed by: Paul Bartel

The Longshot is a 1986 film directed by Paul Bartel starring Tim Conway.
10
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Alec Baldwin, Ian McKellen, Tim Curry

Released: 1994

Directed by: Russell Mulcahy

The Shadow is a 1994 American superhero film, directed by Russell Mulcahy and starring Alec Baldwin, John Lone, Penelope Ann Miller, Ian McKellen, Peter Boyle, Jonathan Winters and Tim Curry. It ...more

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11
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Ringo Starr, John Stamos, Sammy Davis

Released: 1985

Directed by: Harry Harris

Alice in Wonderland is a two-part film adaptation of Lewis Carroll's Alice books. An Irwin Allen production, it was a special made for television and used a huge all-star cast of notable actors ...more
12
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Katy Perry, SofĂ­a Vergara, Joan Rivers

Released: 2011

Directed by: Raja Gosnell

The Smurfs is a 2011 American 3D live-action/computer-animated comedy film loosely based on The Smurfs comic book series created by the Belgian comics artist Peyo and the 1980s animated TV ...more

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13
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Robert De Niro, Whoopi Goldberg, Billy Crystal

Released: 2000

Directed by: Des McAnuff

The Adventures of Rocky and Bullwinkle is a 2000 American live-action/animated adventure comedy film produced by Universal Pictures, based on the television cartoon The Rocky and Bullwinkle Show ...more

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14
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Julius Erving, Stockard Channing, Jonathan Winters

Released: 1979

Directed by: Gilbert Moses

The Fish That Saved Pittsburgh is an American sports/fantasy comedy film that was released in 1979. The movie was directed by Gilbert Moses and co-produced by David Dashev and Gary Stromberg. It ...more
15
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Mr. T, Phyllis Diller, Jonathan Winters

Released: 1987

Alice Through the Looking Glass is a 1987 Australian-Italian animated film nominally based on the novel Through the Looking-Glass by Lewis Carroll. It was directed by Andrea Bresciani and ...more
16
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Hideo Kinoshita, Nobuaki Sekine, Kiyoshi Kawakubo

Released: 1960

Directed by: Osamu Tezuka, Taiji Yabushita, Daisaku Shirakawa

Alakazam the Great is a 1960 Japanese musical anime film, based on the Chinese novel Journey to the West, and was one of the earliest anime films to be released in the United States. Based on ...more
17
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Mark Hamill, Stan Lee, Hugh Hefner

Released: 2004

Directed by: Mark Hamill

Comic Book: The Movie is a 2004 direct-to-DVD mockumentary starring and directed by Mark Hamill.
18
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Natalie Wood, Peter Falk, Jonathan Winters

Released: 1966

Directed by: Arthur Hiller

Penelope is a 1966 comedy film directed by Arthur Hiller and starring Natalie Wood, Ian Bannen, Peter Falk, Jonathan Winters, and Dick Shawn. A novelisation of the screenplay was written by ...more
19
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Ben Stein, Jonathan Winters, Victoria Jackson

Released: 2002

Directed by: John A. Davis

Santa vs. the Snowman 3D is a half-hour computer-animated short, created by Steve Oedekerk and produced by O Entertainment. Originally made as a television special, the film was later presented ...more
20
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Jonathan Winters, Rob Paulsen, Don Messick

Released: 1994

Directed by: Robert Alvarez

Yogi the Easter Bear is an animated TV special from Hanna-Barbera first aired on syndication on April 3, 1994 starring Yogi Bear. This was the last time Don Messick voiced both Boo Boo and ...more
21
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The Bears Who Saved Christmas Jonathan Winters, Brad Garrett, Pam Dawber

Released: 1994

Directed by: Allen Foster

The Bears Who Saved Christmas is a 1994 Animation, Short, Adventure and Family film written by Rachel Koretsky and Steven Whitestone and directed by Allen Foster.
22
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The Wish That Changed Christmas Jonathan Winters
23
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Tim Curry, Jonathan Winters

Released: 1995

Directed by: Tony Collingwood

Daisy-Head Mayzie is a 1995 short animated family TV movie directed by Tony Collingwood and written by Dr. Seuss.
24
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Jacqueline Bissett, Jonathan Winters, Nell Carter

Released: 2003

Directed by: Martin Guigui

Swing is an American romantic comedy film starring Constance Brenneman, Innis Casey, Tom Skerritt, Jacqueline Bisset, Jonathan Winters, Nell Carter, Dahlia Waingort, Adam Tomei, Barry Bostwick, ...more
25
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Sonic Boom Jonathan Winters, Sal Mineo, Johnny Crawford

Released: 1974

Sonic Boom is a 1974 short comedy film.