To me, nothing says soulmates like co-starring in a string of movies. And yes, I know that screen teams were set up by studio executives and had no real control over whether they made two films together or ten. But some on-screen couples had off-screen chemistry, and it just begs the question of what might have been.
Errol Flynn and Olivia de Havilland made eight movies together between 1935 and 1941. Beloved by audiences for their charm, wit, swashbuckling, and screen chemistry, their adventure romances were some of Warner Brothers' biggest hits of the late 1930s. After their partnership ended, Olivia went on to win an Oscar while Errol faced a steady decline in both health and reputation. However, for a few shining years, they were Hollywood's golden couple. Of all the co-stars who never got together, Errol and Olivia might have been the closest.
Errol and Olivia made their first movie together, Captain Blood, in 1935. They were both relatively unknown - Errol was an Australian-born actor who had played bit parts in British films before arriving in Hollywood in 1935, and Olivia was a 19-year-old with one movie under her belt: A Midsummer Night's Dream. Captain Blood, a swashbuckling pirate romance, was a major hit at the box office. Two years after its release, Errol was Warner Brothers' #1 star.
The following year, they made their second co-starring adventure, The Charge of the Light Brigade. "By the time we made The Charge of the Light Brigade, I was sure I was in love with her," Errol wrote in his autobiography. At this point, Errol was married to actress Lili Damita, whom he had met on the boat from England to the U.S. Olivia had her own feelings for Errol, as she stated in several interviews before her death. They played pranks on each other on the sets of their movies, like when Errol hid a dead snake in Olivia's costume during The Charge of the Light Brigade. While making The Adventures of Robin Hood in 1937, Olivia purposefully messed up takes while Errol's wife Lili looked on. "And so we had one kissing scene, which I looked forward to with great delight. I remember I blew every take, at least six in a row, maybe seven, maybe eight, and we had to kiss all over again," she said in an interview.
In 1937, Errol and Olivia attended a coronation ball for England's King George VI at the Coconut Grove nightclub in Los Angeles. There, Errol told Olivia he was in love with her while they danced to "Sweet Leilani" (a Hollywood moment if ever there was one). Olivia told him that she couldn't be in a relationship with him until he got a divorce from Lili. Later in the year, Errol and Lili reunited, and nothing ever came of his slow-dance confession. Magically, a picture actually exists from that night:
They continued to make films together, with 1938's Robin Hood being their biggest success. It was Warner Brothers' most expensive film to date and their first time using three-strip Technicolor, which produces gorgeous, vibrant colors. Their last co-starring movie was 1941's They Died With Their Boots On. Olivia began to make more serious dramas and won a lawsuit against Warner Brothers in 1943 that established the De Havilland Law, preventing studios from keeping their stars in prolonged contracts.
Errol never quite broke out of his stereotypical swashbuckling persona, despite a few dramatic efforts like Green Light. His reputation for heavy drinking and womanizing steadily damaged his screen image until he struggled to find studios that would hire him. As Olivia's fame grew, Errol's declined. He passed away in 1959, only 50 years old, while she lived until 104.
The story of Errol and Olivia doesn't have a happy ending, but it has its shining moments, much like their relationship. Like other co-stars of the era, they became famous and beloved through their efforts as a team before audiences got to know their individual personas. It's impossible to know exactly what happened or how they felt - would Errol's life have been happier if he'd been with Olivia? What if they'd met before he was married? We can imagine whatever we want, but one thing is certain, and that's the timelessness of Errol Flynn and Olivia de Havilland's screen chemistry.
(P.S. I love casual photos like this one from the Dodge City press tour. Look at them holding hands!)
Errol and Olivia were so beautiful together, especially in Robin Hood, for me. They certainly seemed to share a special love for each other.
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