This legendary couple appeared in 8 films together from 1935 to 1941, all for Warner Bros. Actually it's 9 if you count the 1943 musical Thank Your Lucky Stars, where the pair play themselves. They made a varied mix of swashbucklers, westerns, comedy, and period films. Their first pairing came in the rousing Captain Blood (1935), which was Flynn's first starring role, making him an overnight sensation. Olivia had already appeared in three films prior to Captain Blood. I've seen this film twice and it's a beaut. Terrific action sequences and the undeniable chemistry of Flynn and de Havilland on full display. Olivia beat out Jean Arthur and Bette Davis for the role of Arabella Bishop and the rest is history. Blood was so successful Warner Bros quickly paired the duo up the next year for The Charge Of The Light Brigade.
Set in 1854 India, the film had Flynn cast as a British officer fighting the Russians in The Crimean War. Olivia plays Flynn's fiancee. I have yet to see this film so I can't critique on it. But it sounds interesting. For their next film together would be their masterpiece, The Adventures of Robin Hood (1938). Everyone knows the legend of Hood and Flynn was positively electric as the dashing archer. Olivia was equally as good as Maid Marian. Everything came together for this entertaining film. To this day, I still say this is the most vibrant and gorgeous looking film ever made. And one of the best music scores in history.
Screwball comedy was in it's heyday during this time and Warner Bros decided to pair up Errol and Olivia for one called Four's A Crowd (1938). This is another of the duo's films that I have yet to see and since screwball comedy is my favorite genre, I am hankering to see it.
I did see their next film though, the terrific western Dodge City (1939). And let me tell ya something, Errol looks just as comfortable firing six shooters like he does shooting a bow and arrow or swordplay. Dodge City is one of the best westerns ever made and solidified Flynn and de Havilland as one of the premiere on screen couples in film.
They switched gears for their next film, with the historial drama The Private Lives of Elizabeth and Essex. And while this is not solely a Flynn and De Havilland production because of Bette Davis top billed role, this film showed that Errol and Olivia could make just about any type of film.
When Santa Fe Trail (1940) debuted, it marked the pair's seventh outing and it was another huge success. While it was a very entertaining western, I liked Dodge City more. Santa Fe did have an outstanding supporting cast of newcomers such as Ronald Reagan and Van Heflin.
And lastly, for their final film together, came 1941's They Died With Their Boots On, an film based on General George Custer and his infamous last stand. Another western and another solid hit. At this point, Olivia's star was rising and she wanted more starring roles, so the pair parted ways after a successful 8 film run. They firmly established themselves as the ideal romantic leads of Hollywood period adventures. No doubt. And while Olivia went on to have a successful career post Flynn, he was not as fortunate. Still but before his career ended, he did turn in two top notch performances in The Sun Also Rises (1957) and Too Much, Too Soon (1958). But we will always have those 8 wonderful films he and Olivia did. Nothing can ever change that.