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The Best Errol Flynn Movies

Updated June 14, 2019 7.0k votes 1.1k voters 64.5k views52 items

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

Romance! Intrigue! Swashbuckling! This is a list of the best Errol Flynn movies, ranked best to worst with movie trailers when available. During the Golden Age of Hollywood, dashing actor Errol Flynn'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 Errol Flynn movies is decided by how many votes they receive, so only highly rated Errol Flynn movies will be at the top of the list. Errol Flynn has been in a lot of films, so people often debate each other over what the greatest Errol Flynn movie of all time is. If you and a friend are arguing about this then use this list of the most entertaining Errol Flynn films to end the squabble once and for all.

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

Examples of films on this list include The Prince and the Pauper and Edge of Darkness.

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

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  • 1
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    35

    The Adventures of Robin Hood

    Olivia de Havilland, Errol Flynn
    The Adventures of Robin Hood is a 1938 American swashbuckler film directed by Michael Curtiz...  more

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    #132 of 1,195 Every Oscar Winning Film Ever#1371 of 1,506 The Most Rewatchable Movies

  • 2
    294
    25

    Captain Blood

    Olivia de Havilland, Errol Flynn
    Captain Blood is a 1935 American swashbuckling film directed by Michael Curtiz and starring...  more

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    #67 of 196 The Best Adventure Movies#50 of 225 The Best Black and White Movies Ever Made

  • 3
    268
    27

    The Sea Hawk

    Errol Flynn, Claude Rains
    The Sea Hawk is a 1940 American Warner Bros. feature film starring Errol Flynn as an English...  more
  • 4
    226
    32

    They Died with Their Boots On

    Olivia de Havilland, Errol Flynn
    This film is a 1941 American western film directed by Raoul Walsh and starring Errol Flynn and...  more

    More They Died with Their Boots On 

    #16 of 28 Civil War Movies List#146 of 376 The 50+ Best War Movies Ever Made, Ranked

  • 5
    195
    38

    Gentleman Jim

    Errol Flynn, Ward Bond
    Gentleman Jim is a 1942 film starring Errol Flynn as heavyweight boxing champion James J....  more
  • 6
    183
    31

    The Charge of the Light Brigade

    Olivia de Havilland, David Niven
    The Charge of the Light Brigade is a 1936 American historical adventure film made by Warner...  more
  • 7
    180
    36

    Adventures of Don Juan

    Errol Flynn, Raymond Burr
    Adventures of Don Juan, known in the United Kingdom as The New Adventures of Don Juan, is a...  more
  • 8
    160
    32

    The Dawn Patrol

    David Niven, Errol Flynn
    The Dawn Patrol is a 1938 American war film, a remake of the pre-Code 1930 film of the same...  more
  • 9
    161
    40

    Objective, Burma!

    Errol Flynn, James Brown
    Objective, Burma! is a 1945 war film which was loosely based on the six-month raid by...  more
  • 10
    172
    34

    Dodge City

    Olivia de Havilland, Errol Flynn
    Dodge City is a 1939 American Western film directed by Michael Curtiz and starring Errol...  more
  • 11
    148
    48

    The Private Lives of Elizabeth and Essex

    Bette Davis, Olivia de Havilland
    The Private Lives of Elizabeth and Essex is a 1939 American historical romantic drama film...  more

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    #27 of 88 The Best Bette Davis Movies#74 of 87 The Best Vincent Price Movies

  • 12
    147
    35

    Santa Fe Trail

    Ronald Reagan, Olivia de Havilland
    Santa Fe Trail is a 1940 American western film directed by Michael Curtiz and starring Errol...  more

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    #40 of 51 Free Movies! The Best Films In The Public Domain#31 of 205 The Best Movies of 1940

  • 13
    116
    30

    San Antonio

    Errol Flynn, Monte Blue
    San Antonio is a 1945 Western Technicolor film starring Errol Flynn and Alexis Smith. The...  more
  • 14
    97
    25

    Edge of Darkness

    Errol Flynn, Ann Sheridan
    Edge of Darkness is a 1943 World War II film directed by Lewis Milestone that features Errol...  more
  • 15
    111
    30

    Desperate Journey

    Ronald Reagan, Errol Flynn
    Desperate Journey is a 1942 American World War II action and aviation film starring Errol...  more
  • 16
    119
    35

    Virginia City

    Humphrey Bogart, Errol Flynn
    Virginia City is a 1940 American Western film directed by Michael Curtiz and starring Errol...  more

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    #214 of 400 The Best Western Movies Ever Made#18 of 49 The Best 1940s Western Movies

  • 17
    103
    30

    The Master of Ballantrae

    Errol Flynn, Felix Aylmer
    The Master of Ballantrae is a 1953 British Technicolor adventure film starring Errol Flynn and...  more
  • 18
    95
    26

    Northern Pursuit

    Errol Flynn, Monte Blue
    Northern Pursuit is a 1943 World War II film directed by Raoul Walsh and starring Errol Flynn...  more
  • 19
    88
    28

    Rocky Mountain

    Errol Flynn, Slim Pickens
    Rocky Mountain is a 1950 western film directed by William Keighley and starring Errol Flynn....  more
  • 20
    91
    37

    Against All Flags

    Maureen O'Hara, Errol Flynn
    Against All Flags is a 1952 American pirate film starring Errol Flynn as Brian Hawke, Maureen...  more
  • 21
    77
    21

    Silver River

    Errol Flynn, Ann Sheridan
    Silver River is a 1948 western film directed by Raoul Walsh and starring Errol Flynn and Ann...  more
  • 22
    73
    20

    Uncertain Glory

    Errol Flynn, Paul Lukas
    Uncertain Glory is a 1944 film directed by Raoul Walsh and starring Errol Flynn and Paul Lukas...  more
  • 23
    80
    34

    Dive Bomber

    Errol Flynn, Fred MacMurray
    Dive Bomber is a 1941 American aviation film directed by Michael Curtiz and starring Errol...  more
  • 24
    124
    88

    The Prince and the Pauper

    Errol Flynn, Claude Rains
    The Prince and the Pauper is a 1937 film adaptation of the novel of the same name by Mark...  more
  • 25
    67
    35

    The Sun Also Rises

    Ava Gardner, Errol Flynn
    The Sun Also Rises is a 1957 film adaptation of the Ernest Hemingway novel of the same name...  more