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The Best Jonathan Winters Movies

Updated June 11, 2019 371 votes 61 voters 6.2k views35 items

List RulesVote 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?"

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  • 1
    The Russians Are Coming, the Russians Are Coming is a 1966 American comedy film directed by...  more

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    #241 of 376 The 50+ Best War Movies Ever Made, Ranked#634 of 923 The All-Time Greatest Comedy Films

  • 2
    25
    6

    The Loved One

    James Coburn, Milton Berle
    The Loved One is a 1965 black and white comedy film about a business in Los Angeles, which is...  more
  • 3
    21
    2

    Viva Max!

    Peter Ustinov, Jonathan Winters
    Viva Max! is a 1969 comedy film starring Peter Ustinov, Jonathan Winters and John Astin,...  more
  • 4
    18
    2

    Moon over Parador

    Dana Delany, Richard Dreyfuss
    Moon over Parador is a 1988 romantic comedy film, starring Richard Dreyfuss, Raúl Juliá and...  more
  • 5
    24
    9

    The Flintstones

    Halle Berry, Elizabeth Taylor
    The Flintstones is a 1994 American buddy comedy film directed by Brian Levant and written by...  more

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    #360 of 440 Your Favorite Movies of the 1990s#12 of 24 Movies You Loved As A Child That Just Don't Hold Up

  • 6
    19
    4

    The Thief and the Cobbler

    Sean Connery, Matthew Broderick
    This film is a British animated fantasy film directed, co-written and co-produced by Canadian...  more

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    #207 of 534 The Best Animated Films Ever#84 of 113 The Absolute Worst Animated Movies

  • 7
    13
    0

    The Longshot

    Stella Stevens, Jonathan Winters
    The Longshot is a 1986 film directed by Paul Bartel starring Tim Conway....  more
  • 8
    16
    3

    The Shadow

    Alec Baldwin, Ian McKellen
    The Shadow is a 1994 American superhero film, directed by Russell Mulcahy and starring Alec...  more

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    Everything Doctor Strange Basically Stole from The Shadow#51 of 116 The Worst Superhero Movies Ever Made

  • 9
    12
    0

    Tiny Toon Adventures: How I Spent My Vacation

    Jonathan Winters, Danny Cooksey
    Tiny Toon Adventures: How I Spent My Vacation is a 1992 American direct-to-video animated film...  more
  • 10
    14
    6

    Alice in Wonderland

    Ringo Starr, John Stamos
    Alice in Wonderland is a two-part film adaptation of Lewis Carroll's Alice books. An Irwin...  more
  • 11
    14
    6

    The Smurfs

    Katy Perry, Sofía Vergara
    The Smurfs is a 2011 American 3D live-action/computer-animated comedy film loosely based on...  more

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    #69 of 91 The Funniest Movies About Family#86 of 117 The Best Movies Based on TV Shows

  • 12
    10
    2

    The Adventures of Rocky and Bullwinkle

    Robert De Niro, Whoopi Goldberg
    The Adventures of Rocky and Bullwinkle is a 2000 American live-action/animated adventure...  more

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    #42 of 59 The Best Movies Released July 4th Weekend#42 of 116 The Best Comedy Movies for 11-Year-Old Kids

  • 13
    12
    6

    The Fish That Saved Pittsburgh

    Julius Erving, Stockard Channing
    The Fish That Saved Pittsburgh is an American sports/fantasy comedy film that was released in...  more
  • 14
    15
    13

    It's a Mad, Mad, Mad, Mad World

    Mickey Rooney, Spencer Tracy
    It's a Mad, Mad, Mad, Mad World is a 1963 American epic comedy film produced and directed by...  more

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    #764 of 1,195 Every Oscar Winning Film Ever#36 of 170 The Most Rewatchable Comedy Movies

  • 15
    6
    2

    Alice Through the Looking Glass

    Mr. T, Phyllis Diller
    Alice Through the Looking Glass is a 1987 Australian-Italian animated film nominally based on...  more
  • 16
    2
    2

    Alakazam the Great

    Hideo Kinoshita, Nobuaki Sekine
    Alakazam the Great is a 1960 Japanese musical anime film, based on the Chinese novel Journey...  more
  • 17
    6
    0

    Comic Book: The Movie

    Mark Hamill, Stan Lee
    Comic Book: The Movie is a 2004 direct-to-DVD mockumentary starring and directed by Mark...  more
  • 18
    6
    2

    Penelope

    Natalie Wood, Peter Falk
    Penelope is a 1966 comedy film directed by Arthur Hiller and starring Natalie Wood, Ian...  more
  • 19
    4
    4

    Santa vs. the Snowman 3D

    Ben Stein, Jonathan Winters
    Santa vs. the Snowman 3D is a half-hour computer-animated short, created by Steve Oedekerk and...  more
  • 20
    0
    0

    Yogi the Easter Bear

    Jonathan Winters, Rob Paulsen
    Yogi the Easter Bear is an animated TV special from Hanna-Barbera first aired on syndication...  more
  • 21
    2
    0

    The Bears Who Saved Christmas

    Jonathan Winters, Brad Garrett
    The Bears Who Saved Christmas is a 1994 Animation, Short, Adventure and Family film written by...
  • 22
    2
    2

    The Wish That Changed Christmas

    Jonathan Winters
  • 23
    0
    0

    Daisy-Head Mayzie

    Tim Curry, Jonathan Winters
    Daisy-Head Mayzie is a 1995 short animated family TV movie directed by Tony Collingwood and...  more
  • 24
    6
    2

    Swing

    Jacqueline Bissett, Jonathan Winters
    Swing is an American romantic comedy film starring Constance Brenneman, Innis Casey, Tom...  more
  • 25
    0
    0

    Sonic Boom

    Jonathan Winters, Sal Mineo
    Sonic Boom is a 1974 short comedy film....