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The Best Errol Flynn Movies

Updated June 14, 2019 6.4k votes 1.1k voters 64.2k 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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  • The Adventures of Robin Hood1
    371
    35

    The Adventures of Robin Hood

    Olivia de Havilland, Errol Flynn

    Released1938

    Directed byMichael Curtiz, William Keighley

    The Adventures of Robin Hood is a 1938 American swashbuckler film directed by Michael Curtiz... more on Wikipedia

    More The Adventures of Robin Hood 

    #131 of 1,189 Every Oscar Winning Film Ever#1440 of 1,540 The Most Rewatchable Movies

  • Captain Blood2
    311
    26

    Captain Blood

    Olivia de Havilland, Errol Flynn

    Released1935

    Directed byMichael Curtiz

    Captain Blood is a 1935 American swashbuckling film directed by Michael Curtiz and starring... more on Wikipedia

    More Captain Blood 

    #50 of 224 The Best Black and White Movies Ever Made#2 of 143 The Best Swashbuckler Movies

  • The Sea Hawk3
    281
    29

    The Sea Hawk

    Errol Flynn, Claude Rains

    Released1940

    Directed byMichael Curtiz

    The Sea Hawk is a 1940 American Warner Bros. feature film starring Errol Flynn as an English... more on WikipediaAmazon buy button
  • They Died with Their Boots On4
    237
    34

    They Died with Their Boots On

    Olivia de Havilland, Errol Flynn

    Released1941

    Directed byRaoul Walsh

    This film is a 1941 American western film directed by Raoul Walsh and starring Errol Flynn and... more on Wikipedia

    More They Died with Their Boots On 

    #18 of 28 Civil War Movies List#142 of 374 The 50+ Best War Movies Ever Made, Ranked

  • Gentleman Jim5
    203
    40

    Gentleman Jim

    Errol Flynn, Ward Bond

    Released1942

    Directed byRaoul Walsh

    Gentleman Jim is a 1942 film starring Errol Flynn as heavyweight boxing champion James J.... more on WikipediaAmazon_watch buy button
  • The Charge of the Light Brigade6
    196
    31

    The Charge of the Light Brigade

    Olivia de Havilland, David Niven

    Released1936

    Directed byMichael Curtiz

    The Charge of the Light Brigade is a 1936 American historical adventure film made by Warner... more on WikipediaAmazon buy button
  • The Dawn Patrol7
    169
    33

    The Dawn Patrol

    David Niven, Errol Flynn

    Released1938

    Directed byEdmund Goulding

    The Dawn Patrol is a 1938 American war film, a remake of the pre-Code 1930 film of the same... more on WikipediaAmazon_watch buy button
  • Dodge City8
    183
    35

    Dodge City

    Olivia de Havilland, Errol Flynn

    Released1939

    Directed byMichael Curtiz

    Dodge City is a 1939 American Western film directed by Michael Curtiz and starring Errol... more on WikipediaAmazon_watch buy button
  • Adventures of Don Juan9
    188
    37

    Adventures of Don Juan

    Errol Flynn, Raymond Burr

    Released1948

    Directed byVincent Sherman

    Adventures of Don Juan, known in the United Kingdom as The New Adventures of Don Juan, is a... more on WikipediaAmazon_watch buy button
  • Objective, Burma!10
    172
    43

    Objective, Burma!

    Errol Flynn, James Brown

    Released1945

    Directed byRaoul Walsh

    Objective, Burma! is a 1945 war film which was loosely based on the six-month raid by... more on WikipediaAmazon_watch buy button
  • The Private Lives of Elizabeth and Essex11
    157
    51

    The Private Lives of Elizabeth and Essex

    Bette Davis, Olivia de Havilland

    Released1939

    Directed byMichael Curtiz

    The Private Lives of Elizabeth and Essex is a 1939 American historical romantic drama film... more on Wikipedia

    More The Private Lives of Elizabeth and Essex 

    #26 of 88 The Best Bette Davis Movies#22 of 41 The Best Movies About Queens

  • The Prince and the Pauper12
    132
    30

    The Prince and the Pauper

    Errol Flynn, Claude Rains

    Released1937

    Directed byWilliam Dieterle, William Keighley

    The Prince and the Pauper is a 1937 film adaptation of the novel of the same name by Mark... more on Wikipedia
  • Santa Fe Trail13
    156
    37

    Santa Fe Trail

    Ronald Reagan, Olivia de Havilland

    Released1940

    Directed byMichael Curtiz

    Santa Fe Trail is a 1940 American western film directed by Michael Curtiz and starring Errol... more on Wikipedia
  • San Antonio14
    121
    31

    San Antonio

    Errol Flynn, Monte Blue

    Released1945

    Directed byRaoul Walsh, Robert Florey, David Butler

    San Antonio is a 1945 Western Technicolor film starring Errol Flynn and Alexis Smith. The... more on Wikipedia
  • Desperate Journey15
    116
    32

    Desperate Journey

    Ronald Reagan, Errol Flynn

    Released1942

    Directed byRaoul Walsh

    Desperate Journey is a 1942 American World War II action and aviation film starring Errol... more on WikipediaAmazon buy button
  • Edge of Darkness16
    102
    26

    Edge of Darkness

    Errol Flynn, Ann Sheridan

    Released1943

    Directed byLewis Milestone

    Edge of Darkness is a 1943 World War II film directed by Lewis Milestone that features Errol... more on WikipediaAmazon buy button
  • Virginia City17
    124
    36

    Virginia City

    Humphrey Bogart, Errol Flynn

    Released1940

    Directed byMichael Curtiz

    Virginia City is a 1940 American Western film directed by Michael Curtiz and starring Errol... more on WikipediaAmazon buy button

    More Virginia City 

    #220 of 399 The Best Western Movies Ever Made#19 of 49 The Best 1940s Western Movies

  • The Master of Ballantrae18
    109
    31

    The Master of Ballantrae

    Errol Flynn, Felix Aylmer

    Released1953

    Directed byWilliam Keighley

    The Master of Ballantrae is a 1953 British Technicolor adventure film starring Errol Flynn and... more on WikipediaAmazon buy button
  • Northern Pursuit19
    101
    28

    Northern Pursuit

    Errol Flynn, Monte Blue

    Released1943

    Directed byRaoul Walsh

    Northern Pursuit is a 1943 World War II film directed by Raoul Walsh and starring Errol Flynn... more on WikipediaAmazon buy button
  • Against All Flags20
    96
    37

    Against All Flags

    Maureen O'Hara, Errol Flynn

    Released1952

    Directed byFred de Cordova, George Sherman

    Against All Flags is a 1952 American pirate film starring Errol Flynn as Brian Hawke, Maureen... more on WikipediaAmazon buy button
  • Rocky Mountain21
    94
    28

    Rocky Mountain

    Errol Flynn, Slim Pickens

    Released1950

    Directed byWilliam Keighley

    Rocky Mountain is a 1950 western film directed by William Keighley and starring Errol Flynn.... more on WikipediaAmazon buy button
  • Silver River22
    82
    22

    Silver River

    Errol Flynn, Ann Sheridan

    Released1948

    Directed byRaoul Walsh

    Silver River is a 1948 western film directed by Raoul Walsh and starring Errol Flynn and Ann... more on WikipediaAmazon buy button
  • Uncertain Glory23
    78
    20

    Uncertain Glory

    Errol Flynn, Paul Lukas

    Released1944

    Directed byRaoul Walsh

    Uncertain Glory is a 1944 film directed by Raoul Walsh and starring Errol Flynn and Paul Lukas... more on WikipediaAmazon buy button
  • The Sun Also Rises24
    72
    35

    The Sun Also Rises

    Ava Gardner, Errol Flynn

    Released1957

    Directed byHenry King

    The Sun Also Rises is a 1957 film adaptation of the Ernest Hemingway novel of the same name... more on Wikipedia
  • Dive Bomber25
    85
    37

    Dive Bomber

    Errol Flynn, Fred MacMurray

    Released1941

    Directed byMichael Curtiz

    Dive Bomber is a 1941 American aviation film directed by Michael Curtiz and starring Errol... more on WikipediaAmazon buy button