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The Best Errol Flynn Movies

Updated June 14, 2019 6.9k votes 1.1k voters 64.9k 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 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 and William Keighley, and starring Errol Flynn, Olivia de Havilland, Basil Rathbone, and Claude Rains....  more

    More The Adventures of Robin Hood 

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  • 2
    290
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    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 Errol Flynn, Olivia de Havilland, Basil Rathbone, and Ross Alexander. The film was made by First National...  more

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  • 3
    266
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    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 privateer who defends his nation's interests on the eve of the Spanish Armada. The film was the tenth...  more
  • 4
    225
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    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 Olivia de Havilland. Written by Æneas MacKenzie and Wally Kline, the film is a highly fictionalized...  more

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  • 5
    199
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    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. Corbett. The supporting cast includes Alexis Smith, Jack Carson, Alan Hale, William Frawley, and Ward Bond....  more
  • 6
    180
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    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 Bros. It was directed by Michael Curtiz and produced by Samuel Bischoff, with Hal B. Wallis as executive...  more
  • 7
    156
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    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 name. Both were based on the short story "The Flight Commander" by John Monk Saunders, an American writer...  more
  • 8
    183
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    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 1948 American adventure Technicolor romance film made by Warner Bros. It was directed by Vincent Sherman...  more
  • 9
    173
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    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 Flynn, Olivia de Havilland, and Ann Sheridan. Based on a story by Robert Buckner, the film is about a Texas...  more
  • 10
    159
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    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 Merrill's Marauders in the Burma Campaign during the Second World War. The film, made by Warner Brothers...  more
  • 11
    149
    47

    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 directed by Michael Curtiz and starring Bette Davis, Errol Flynn, and Olivia de Havilland. Based on the play...  more

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    126
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    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 Twain. It starred Errol Flynn, twins Billy and Bobby Mauch in the title roles, and Claude Rains. The film was...  more
  • 13
    146
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    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 Flynn, Olivia de Havilland, Raymond Massey and Ronald Reagan. Written by Robert Buckner, the film is about...  more

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  • 14
    116
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    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 movie was written by W. R. Burnett and Alan Le May, and directed by David Butler as well as uncredited Robert...  more
  • 15
    111
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    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 Flynn and Ronald Reagan, directed by Raoul Walsh. The supporting cast includes Raymond Massey, Alan Hale, Sr....  more
  • 16
    121
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    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 Flynn, Miriam Hopkins, Randolph Scott, and a mustachioed Humphrey Bogart in the role of the real-life...  more

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    106
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    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 Roger Livesey. It is a loose and highly truncated adaptation of the Robert Louis Stevenson novel of the...  more
  • 18
    97
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    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 as a member of the Royal Canadian Mounted Police who tries to uncover a Nazi plot against the Allied war...  more
  • 19
    91
    26

    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. The film is set near the end of the American Civil War....  more
  • 20
    79
    20

    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 Sheridan. The film is based on a Stephen Longstreet novel....  more
  • 21
    94
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    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 O'Hara as Prudence "Spitfire" Stevens and Anthony Quinn as Roc Brasiliano. The film's plot is set in...  more
  • 22
    99
    15

    Crossed Swords

    Errol Flynn, Gina Lollobrigida

    Released1954

    Directed byMilton Krims, Vittorio Vassarotti

    Crossed Swords is a 1954 Italian made swashbuckler film starring Errol Flynn. It was also known as Il Maestro di Don Giovanni and The Golden Blade....  more
  • 23
    73
    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 and....  more
  • 24
    68
    34

    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 directed by Henry King. The screenplay was written by Peter Viertel and it starred Tyrone Power, Ava...  more
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    80
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    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 Flynn and Fred MacMurray. The film is notable for both its Technicolor photography of pre-World War II...  more