Both Errol and Olivia were screen newcomers when they appeared in their first film together Captain Blood. Olivia was only 18. Errol only got a part in the film because Robert Donat, who was originally to play Dr. Peter Blood, dropped out. Warners scrambled to find a replacement and took a chance on Flynn.
From 1935-1941 they would make eight full-length feature films together. Their third pairing would end up to be their best, the 1938 film The Adventures Of Robin Hood. It's almost like this is the climax of their partnership. The film in still a classic and is most likely the best Robin Hood film ever created. This is the model for all the versions to come.
Flynn and de Havilland were never an official pair. In fact, they both weren't the big stars at Warner Bros. during the 1930s and early 1940s. So that was most likely the reason they were paired up so often. I also suspect that that is why they also had the same sort of roles. Flynn the heroic swashbuckler of some sort and de Havilland the sweet girl with a bit of sass. It's clear that these eight films they made together weren't made for the benefit of their film partnership. Unlike Fred Astaire and Ginger Rogers movies, you couldn't predict the ending. It wasn't clear if Flynn's character would end up with de Havilland's at the end. Nor was it clear that Flynn's character would even survive till the end. There was only one film that was an odd one out for the pair and that was Four's A Crowd in 1938. It was the only romantic comedy the two made together. One thing that was always the same was the amazing chemistry between them.
The two were never involved romantically. They both did have an affection for each other. Never an ounce of bitterness between the two. They made their last film together in 1941: They Died With Their Boots On. Their last scene together in the film is that of a husband and wife saying good-bye, as if they know they'll never see each other alive again. That scene, in a way, is that of Flynn and de Havilland saying good-bye. Flynn's character looks at Olivia and says, Walking through life with you, ma'am, has been a very gracious thing.. They embrace and kiss and he walks off. They show Olivia and the camera pans back and she faints. That whole scene is a symbol of their six-year partnership ending. Color me a sap, but I shed a few tears at that moment.
Their films together:
Captain Blood (1935)
The Charge Of The Light Brigade (1936)
The Adventures Of Robin Hood (1938)
Four's A Crowd (1938)
Dodge City (1939)
The Private Lives Of Elizabeth And Essex (1939)
Sante Fe Trail (1940)
They Died With Their Boots On (1941)