Hollywood's Golden Era Leading Actress, Olivia de Havilland, And Her Real Life Love Interests

Date March 23, 2018 18:06

Long before Angelina Jolie or Jennifer Lawrence, there was Olivia de Havilland. She was one of the leading female actresses of Hollywood's golden age. Needless to say, she had her pick of men.


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Illustrious career

The iconic actress who starred in the classic 1939 film, Gone With the Wind, turned 101 in 2017. And she is still very passionate when she engages with fans on her illustrious 53-year career.


Her first recorded acting job was an appearance on an LA production of Shakespeare's A Midsummer Night’s Dream at 18. Her effort earned her great reviews and a contract with Warner Bros. Studios.


She went on to star in numerous films including The Adventures of Robin Hood, considered by the United States Library of Congress as “culturally, historically, or aesthetically significant”. 

She was nominated 5 times by the Academy for Best Actress in a Leading Role and won twice.

The leading men she dated.

It is not easy to determine every single man she had intimate affairs with because, apparently, this was long before the word paparazzi became a thing, but somehow, in the 30s and 40s, the world still goes around.

The actress, who featured in no less than 49 feature films to her credit, is known to have kicked it off with a number of Hollywood hunks, including Clark Gable and James Stewart.

Here's a list of De Havilland's men:

Brian Aherne


The English actor was known for his work on stage and on screen. He also has some silent films to his credit. His notable works include King of the Castle, Safety First, and Quality Street. He is known to have dated De Havilland and married her sister, Joan Fontaine

Burgess Meredith


The American actor and cross-disciplinary director had a career spanning 60 years. He is considered one of the most accomplished actors of his time. He is known for his work on Rocky, Of Mice and Men and Batman. He was married 5 times and dated about 6 women, including De Havilland

Clark Gable


Regarded as 'The King of Hollywood' in his prime, Clark Gable could have his pick of women. Think George Clooney or Idris Elba. He was married 5 times and dated no less than 30 women, including Nancy Reagan and Grace Kelly.

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George Brent


Brent is most remembered for his film The Great Lie. He was married 5 times and dated De Havilland in 1938.

James Stewart


Stewart was reportedly in a relationship with De Havilland from 1939 - 1942. He was also associated with a long list of leading female actresses in his time, including Katherine Hepburn and Joan Crawford. 

Strained relationship with her sister

De Havilland was born in Tokyo and only came to live in the U.S. when her family made a diversion after she and her sister fell sick. They were on their way to Britain but ended up staying in California.


She and her sister, the actress, Joan Fontaine, did not get along. In fact, she changed her last name primarily to distance herself from her sister.

In 1962, the twice married actress published a book on French culture titled Every Frenchman Has One. She has admitted in detail that she and Errol Flynn, with whom she starred in 6 films, shared an emotional connection that they never acted on.

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