Loosely coupled for decades, they made one of the most iconic pairings in cinema history. This tremendous onscreen attraction of theirs eventually led to them frequently appearing on screen, and coupled with memorable pairings, made them an integral part of the Hollywood golden age. Together, the two- who would go on to star in eight films together- had one of the most successful partnerships of classic film.
Their initial collaboration was Captain Blood, helmed by Michael Curtiz. Flynn played the footloose pirate, Peter Blood, and de Havilland the love interest, Arabella Bishop. The movie was a smash hit and launched one of Hollywood’s most famous on-screen pairings. Flynn’s charisma and swashbuckling heroism combined effortlessly with de Havilland’s image as a strong-willed, intelligent woman, establishing a dynamic for their future collaborations.
### 2. **The Charge of the Light Brigade (1936)**
The following year, Flynn and de Havilland reunited for *The Charge of the Light Brigade*, a historical drama about the infamous military disaster during the Crimean War. While their roles were not as romantically charged as in *Captain Blood*, the film featured their familiar dynamic of strong personalities facing difficult circumstances. Flynn played the heroic Major Vickers, while de Havilland starred as the love interest, Lady Vivian, adding another layer to their cinematic partnership.
### 3. **The Adventures of Robin Hood (1938)**
Perhaps their most famous and beloved collaboration, *The Adventures of Robin Hood* is a timeless classic that cemented both actors’ places in film history. Flynn’s portrayal of the legendary outlaw Robin Hood and de Havilland’s portrayal of Maid Marian are iconic roles that have been adored by audiences for generations. The film was a massive success, and their chemistry as the daring hero and his virtuous love interest became the standard for the swashbuckling genre. This film is widely regarded as one of the greatest adventure films ever made.
### 4. **Dodge City (1939)**
In *Dodge City*, a Western directed by Michael Curtiz, Flynn played a lawman named Wade Hatton, who seeks to bring order to a wild frontier town. De Havilland starred as the feisty and independent Ruby, a woman who finds herself caught between Flynn’s character and the violence of the frontier. The film was another successful pairing of the two stars, though it featured a more traditional Western plot than their previous adventures.
### 5. **The Private Lives of Elizabeth and Essex (1939)**
*The Private Lives of Elizabeth and Essex* saw Flynn and de Havilland in a historical drama set in the reign of Queen Elizabeth I. Flynn portrayed the infamous Robert Devereux, the Earl of Essex, while de Havilland took on the role of Queen Elizabeth. Their roles in this film were a departure from their usual swashbuckling adventures, with de Havilland portraying a more commanding, regal character while Flynn’s character struggled with ambition and betrayal. Their performances were a stark contrast to their earlier romantic roles, showcasing the range of their talents.
### 6. **The Sea Hawk (1940)**
In *The Sea Hawk*, Flynn again took on the role of a daring pirate, while de Havilland played the beautiful and strong-willed Lady Viola. The film was a classic example of the adventure genre, with Flynn’s swashbuckling hero and de Havilland’s determined heroine once again playing off each other’s strengths. Their chemistry was still evident, and the film was another success for the duo, cementing their status as one of Hollywood’s most beloved on-screen pairs.
### 7. **They Died with Their Boots On (1941)**
In *They Died with Their Boots On*, Flynn portrayed General George Armstrong Custer, the iconic and tragic figure of the American frontier. De Havilland played Elizabeth Bacon, Custer’s wife. The film was a biographical drama that told the story of Custer’s rise to fame and his eventual demise at the Battle of Little Bighorn. While it was not as widely acclaimed as some of their previous films, it still showcased the strong partnership between Flynn and de Havilland, even as they tackled more serious historical subject matter.
### 8. **Santa Fe Trail (1940)**
Their final collaboration, *Santa Fe Trail*, was a Western epic about the life of Confederate General J.E.B. Stuart, played by Flynn, and his relationship with his fellow soldiers, including de Havilland’s character, who portrayed the spirited and independent Kit Carson Holliday. Though the film was a more traditional historical Western, it provided the last opportunity for audiences to see Flynn and de Havilland together on screen.
### Conclusion
The partnership between Errol Flynn and Olivia de Havilland is one of Hollywood’s most cherished, with the two stars appearing together in eight films that spanned a vari