Errol Flynn and Olivia de Havilland
This is my favorite classic couple of all time! Olivia de Havilland and Errol Flynn (drool!)
Both were incredibly beautiful people. They both made a total of 8 movies together. Their first movie was Captain Blood. They almost didn't end up together in this movie, the original leads were supposed to be Bette Davis and Robert Donat. Donat got sick so George Brent was tried for the role, he didn't look too good in the historical costumes so Flynn got it. Davis had schedual problems so an unknown named Olivia de Havilland got hired. This was a risky move. Two unknowns in a major production. But the choice proved incredibly successful. The New York Post wrote "If you haven't heard of Errol Flynn, it won't be long now." The Daily Mirrorcalled him the next Valentino. Olivia de Havilland recieved five thousand marriage proposals and was called "a lady of rapturous loveliness and well worth fighting for."(New York Times).
Most of their movies would consist of westerns and other costume films. Errol Flynn always played the dashing hero with eyes only for De Havilland. De Havilland's character was always the proper ladylike heroine who never gave into his magnetic charm too easily.
Their most famous film was The Adventures of Robin Hood, this film is a classic. De Havilland is smart and sassy. Errol Flynn is the perfect Robin Hood, cocky and brave.
They were the odd actors at Warner Bros. The depression studio's major stars were gritty and tough like Cagney, Boghart and Bette Davis. Pretty boy Errol Flynn and the ladylike Olivia de Havilland were the odd ones out. Warner Bros. didn't really know what to do with a talented actress like De Havilland and they put her in roles she never really liked. She finally rebelled and sued. She went on to win a Academy award and a Oscar for the movies To Each His Own and The Heiress.
They never became real life lovers. De Havilland did admit to having a bit of a crush on him. Flynn also had feelings for De Havilland, he claimed he had an "ardor for her". He would play school boy tricks like putting a dead snake in her underwear. Some claimed that he later insisted on saying all flattering dialog to her himself and was jealous on anyone who tried to talk with her other than himself. Bette Davis theorized decades later that "it was Olivia de Havilland whom Flynn truly adored and who evaded him successfully in the end. I really believe that he was deeply in love with her."
Then again Davis never really liked Flynn much so how come she thought she knew him so well? They're movies:
Captain Blood*(1935)<---kinda outdated but what the heck?
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)
Santa Fe Trail*(1940)
They Died with Their Boots On*(1941)

some links!
Errol Flynn Page
Olivia de Havilland Superstar Page