The Best Errol Flynn Movies

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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 vote it up 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 and 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.

Most divisive: King's Rhapsody
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  • The Adventures of Robin Hood
    Errol Flynn, Olivia de Havilland, Basil Rathbone
    589 votes
    • Released: 1938
    • Directed by: Michael Curtiz, William Keighley

    This swashbuckler film chronicles the legendary exploits of Robin Hood and his band of merry outlaws, focusing on their fight against tyranny in medieval England. Errol Flynn's portrayal of the dashing hero Robin Hood cemented his status as one of the greatest screen legends of all time, giving a charismatic and energetic performance that delighted audiences. With its thrilling action sequences, lush Technicolor cinematography, and strong supporting cast, the film has endured as a beloved classic and remains the definitive version of the Robin Hood legend. Undoubtedly, this masterpiece has influenced countless adaptations of the iconic tale for generations.

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  • Captain Blood
    Errol Flynn, Olivia de Havilland, Basil Rathbone
    494 votes
    • Released: 1935
    • Directed by: Michael Curtiz

    As an exhilarating adventure on the high seas, this movie centers around a group of wrongly convicted rebels who escape from a British prison and turn to piracy under the leadership of Captain Peter Blood, a former physician. Flynn's breakthrough role as the dashing, fearless, and morally driven Captain Blood showcased his natural charisma and athletic prowess, paving the way for his future career as an action star. Tightly paced storytelling, captivating performances, and impressive special effects for its time contribute to the film's enduring appeal and lasting legacy. This swashbuckler classic has continued to inspire pirate stories and action-adventure films since its release.

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  • The Sea Hawk
    Errol Flynn, Brenda Marshall, Flora Robson
    456 votes
    • Released: 1940
    • Directed by: Michael Curtiz

    This rousing adventure film tells the story of an English privateer who, during a time of war with Spain, uncovers a plan to conquer England and usurp Queen Elizabeth I. Flynn's magnetic portrayal of the heroic privateer Captain Geoffrey Thorpe has been hailed as one of his finest cinematic achievements, blending his trademark charm with powerful dramatic moments. The combination of spectacular sea battles, lush period details, and well-crafted dialogue ensures its status as a timeless classic and ranks it among the best of the genre. The film has left an indelible mark on subsequent period adventures and stands as a testament to Flynn's enduring appeal as an action star.

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  • They Died with Their Boots On
    Errol Flynn, Olivia de Havilland, Arthur Kennedy
    400 votes
    • Released: 1941
    • Directed by: Raoul Walsh

    Portraying the life and military career of General George Armstrong Custer, this biographical war film focuses specifically on his controversial role in the Battle of the Little Bighorn. Flynn's compelling performance as Custer paints the historical figure as a complex, flawed but ultimately noble character, showcasing the actor's impressive dramatic range. Despite its historical inaccuracies, the film remains a captivating viewing experience, thanks to its engaging storytelling, strong supporting cast, and authentic production design. This tale of heroism and tragedy has stood the test of time as a memorable depiction of one of America's most famous battles.

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  • Gentleman Jim
    Errol Flynn, Alexis Smith, Jack Carson
    359 votes
    • Released: 1942
    • Directed by: Raoul Walsh

    This biographical sports drama showcases the life and career of James J. Corbett, a 19th-century boxer who revolutionized the sport by incorporating scientific techniques and ultimately became the heavyweight champion of the world. Flynn's enthusiastic and charismatic portrayal of the title character highlights his natural athletic talent and proved he could excel in both action and dramatic roles. The movie's success lies not only in its thrilling boxing sequences but also in its exploration of the social and political landscape of the era. As a result, it has cemented its position as a classic of the sports film genre.

  • The Charge of the Light Brigade
    Errol Flynn, Olivia de Havilland, Patric Knowles
    321 votes
    • Released: 1936
    • Directed by: Michael Curtiz

    Set during the Crimean War, this epic historical drama follows the doomed charge of the British cavalry against Russian forces, focusing primarily on the personal stories of several officers involved. Flynn's commanding performance as the idealistic and passionate Captain Geoffrey Vickers demonstrates his ability to convey both emotional depth and physical prowess in his acting. Bolstered by thrilling battle scenes, a sweeping musical score, and its powerful exploration of loyalty and honor, this film has stood as a lasting example of the historical epic genre. It remains a cinematic tribute to the bravery and sacrifice of those involved in the titular military disaster.

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