Watchworthy

The Best Errol Flynn Movies 

Reference
Originally by
Updated June 14, 2019 7.3k votes 1k voters 63.1k views 52 items

List Rules Vote 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?"

If Errol Flynn movies are your thing, then check out the greatest movies by Tyrone Power and Rod Steiger too.

Data-driven recommendations based on voting from over 40 million monthly visits to Ranker. Try the free app
list ordered by
1
Ranker Video
Olivia de Havilland, Errol Flynn, Claude Rains

Released: 1938

Directed by: Michael 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 ...more

More The Adventures of Robin Hood 

#114 of 599 The Greatest Epic Movies Ever Made #1,160 of 1,699 The Most Rewatchable Movieslisted on Every Oscar Winning Film Ever

2
Ranker Video
Olivia de Havilland, Errol Flynn, Basil Rathbone

Released: 1935

Directed by: Michael 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 ...more

More Captain Blood 

#126 of 212 The Best Adventure Movies #61 of 232 The Best Black and White Movies Ever Made #2 of 134 The Best Swashbuckler Movies

3
Ranker Video
Errol Flynn, Claude Rains, Gilbert Roland

Released: 1940

Directed by: Michael 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
Ranker Video
Olivia de Havilland, Errol Flynn, Anthony Quinn

Released: 1941

Directed by: Raoul 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 ...more

More They Died with Their Boots On 

#153 of 375 The 50+ Best War Movies Ever Made, Ranked #88 of 395 The Best Western Movies Ever Made #13 of 50 The Best 1940s Western Movies

5
Ranker Video
Errol Flynn, Ward Bond, William Frawley

Released: 1942

Directed by: Raoul 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 ...more
6
Ranker Video
Olivia de Havilland, David Niven, Errol Flynn

Released: 1936

Directed by: Michael 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 ...more
7
Ranker Video
Olivia de Havilland, Errol Flynn, Ann Sheridan

Released: 1939

Directed by: Michael 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 ...more
8
Ranker Video
Errol Flynn, James Brown, William Prince

Released: 1945

Directed by: Raoul 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
9
Ranker Video
David Niven, Errol Flynn, Basil Rathbone

Released: 1938

Directed by: Edmund 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 ...more
10
Ranker Video
Errol Flynn, Raymond Burr, Ann Rutherford

Released: 1948

Directed by: Vincent 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 ...more
11
Ranker Video
Bette Davis, Olivia de Havilland, Vincent Price

Released: 1939

Directed by: Michael 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 ...more

More The Private Lives of Elizabeth and Essex 

#48 of 87 The Best Vincent Price Movies #25 of 38 The Best Movies About Royalty

12
Ranker Video
Ronald Reagan, Olivia de Havilland, Errol Flynn

Released: 1940

Directed by: Michael 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 ...more

More Santa Fe Trail 

#178 of 395 The Best Western Movies Ever Made #42 of 58 Free Movies! The Best Films in the Public Domain #17 of 50 The Best 1940s Western Movies

13
Ranker Video
Errol Flynn, Claude Rains, Barton MacLane

Released: 1937

Directed by: William 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 ...more
14
Ranker Video
Humphrey Bogart, Errol Flynn, Randolph Scott

Released: 1940

Directed by: Michael 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

More Virginia City 

#203 of 395 The Best Western Movies Ever Made #19 of 50 The Best 1940s Western Movies #30 of 253 The Best Movies of 1940

15
Ranker Video
Errol Flynn, Monte Blue, Alexis Smith

Released: 1945

Directed by: Raoul 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 ...more

More San Antonio 

14 Chilling Ghost Stories From San Antonio, Texas #209 of 395 The Best Western Movies Ever Made #23 of 50 The Best 1940s Western Movies

16
Ranker Video
Ronald Reagan, Errol Flynn, Arthur Kennedy

Released: 1942

Directed by: Raoul 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 ...more
17
Ranker Video
Errol Flynn, Ann Sheridan, Ruth Gordon

Released: 1943

Directed by: Lewis Milestone

Edge of Darkness is a 1943 World War II film directed by Lewis Milestone that features Errol Flynn, Ann Sheridan and Walter Huston. The feature is based on a script written by Robert Rossen ...more
18
Ranker Video
Errol Flynn, Felix Aylmer, Roger Livesey

Released: 1953

Directed by: William 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 ...more
19
Ranker Video
Errol Flynn, Monte Blue, Gene Lockhart

Released: 1943

Directed by: Raoul 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 ...more
20
Ranker Video
Errol Flynn, Fred MacMurray, Ralph Bellamy

Released: 1941

Directed by: Michael 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
21
Ranker Video
Maureen O'Hara, Errol Flynn, Anthony Quinn

Released: 1952

Directed by: Fred 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 ...more
22
Ranker Video
Ava Gardner, Errol Flynn, Tyrone Power

Released: 1957

Directed by: Henry 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
23
Ranker Video
Errol Flynn, Slim Pickens, Scott Forbes

Released: 1950

Directed by: William 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.
24
Ranker Video
Errol Flynn, Ann Sheridan, Thomas Mitchell

Released: 1948

Directed by: Raoul 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.
25
Ranker Video
Errol Flynn, Paul Lukas, Sheldon Leonard

Released: 1944

Directed by: Raoul Walsh

Uncertain Glory is a 1944 film directed by Raoul Walsh and starring Errol Flynn and Paul Lukas and.