10 Greatest Films of Olivia de Havilland

Robert Frost
The Greatest Films (according to me)
6 min readApr 10, 2017

Olivia de Havilland celebrated her 100th birthday a few days ago. She is one of the last remaining stars of Hollywood’s golden age. She was nominated for five Best Actress in a Leading Role Oscars and won two of them; one for To Each His Own and one for The Heiress. She was nominated for three Golden Globes and won two of them; one for The Heiress and the other for the 1987 television miniseries Anastasia.

Olivia was born in Tokyo, Japan, where her father was teaching at the Imperial University. When she was three, her family decided to move back to England, but paused enroute in California because Olivia and her sister Joan (actress Joan Fontaine) were ill. Her mother, a British stage actress, decided to raise the two girls there, in California.

Her first acting role was as Alice in Wonderland in a local community theatre. A lucky break occurred when she was the second understudy for the role of Hermia in a theatre production of A Midsummer Night’s Dream and both the lead actress and first understudy quit. The director was so impressed that when he, not long after, was assigned to direct a cinematic adaptation of the play, he asked Olivia to star in it. She took the role and gave up her plans to be a teacher. That role earned her a five year contract with Warner Brothers. She went on to make 49 films and continued acting in television movies and mini-series until 1988.

She comes from good genes. Her sister Joan Fontaine lived to be 96, her father lived to be 96, and her mother lived to be 89. Happy 100th birthday Olivia de Havilland.

10. To Each His Own (1946) — The story starts with Olivia as a young woman in love with a soldier during WWI. She becomes pregnant and then he is killed before they can marry. She is forced to give the baby up for adoption. Two decades later, in WWII she has a chance to be with her son. Olivia received her first Oscar for this role.

Holy Canarsie!” — Gregory

9. My Cousin Rachel (1952) — Twenty-seven year old Richard Burton costarred with Olivia in this mystery and received his first Oscar nomination. His character starts to fall for her, even though he suspects she may have killed his cousin and may be after his money.

Because I love her and nothing else! It isn’t a little loving. It isn’t a fancy. It isn’t something you’d turn on and off. It’s everything I think and feel and want and know. And there’s no room in me for anything else. And never will be again.” — Philip Ashley

8. Hold Back the Dawn (1941) — Charles Boyer plays a gigolo trying to get into the United States. His plan is to marry an American schoolteacher in Mexico and through that gain entry and then dump her for the woman he really is pursuing. Billy Wilder co-wrote the script.

You see, I come from a small town. We don’t have any of those fine hotels. We eat at the drugstore… But we leave a tip just the same.” — Emmy

7. Hush…Hush, Sweet Charlotte (1964) — I watched this film just a few days after visiting Houmas House in Burnside and Oak Alley Plantation in Vacherie, the two primary locations where it was filmed. While at Houmas House, our guide told us a story about the filming. Originally the film was to have starred Joan Crawford in Olivia’s role, but just as filming was starting, Bette Davis and Joan Crawford got into a fierce fistfight just outside the house. Crawford received a black eye and quit the film.

It’s a great film full of twists and nastiness.

You just can’t keep hogs away from the trough, can you?” — Miriam

6. Gone With the Wind (1939) — The adaptation of Margaret Mitchell’s epic novel won eight Oscars. Olivia received her first nomination. She plays Scarlett’s best friend and potential love rival.

Oh, Mammy, Mammy! He has lost his mind!” — Melanie

5. The Snake Pit (1948) — Anatole Litvak directed this adaptation of Mary Ward’s novel about a woman’s ordeal at a mental hospital. The film was nominated for six Oscars, including one for de Havilland for Best Actress.

I’ll tell you where it’s gonna end, Miss Somerville… When there are more sick ones than well ones, the sick ones will lock the well ones up.” — Virginia

4. The Heiress (1949) — Montgomery Clift plays a gold digger that once pursued Olivia’s character. The story has her seeking revenge against him. William Wyler directed the film. It received eight Oscar nominations, winning four, including Olivia’s second Best Actress Oscar.

He’s grown greedier over the years. Before he only wanted my money; now he wants my love as well. Well, he came to the wrong house — and he came twice. I shall see that he does not come a third time.” — Catherine Sloper

3. Captain Blood (1935) — Before Errol Flynn clashed swords with Basil Rathbone in Adventures of Robin Hood, he clashed swords with him in this beautiful film that established Errol Flynn as Hollywood’s greatest swashbuckler. He plays a gentlemen and physician sent to Jamaica as a prisoner. He becomes a pirate. Olivia has said that Errol was her favorite co-star. The two did eight films together.

This is interesting. I’ve had men tell me they had reasons for admiring me… and some few have even laid claims to reasons for loving me. But for a man to store up reasons for resenting me… how refreshing! You must tell me a few of them.” — Arabella Bishop

2. The Strawberry Blonde (1941) — Raoul Walsh directed this film that starts Olivia, Jimmy Cagney, and Rita Hayworth (all of whom have posts in work) along with Alan Hale and George Reeves. Jimmy plays a guy that is infatuated with a beautiful redhead (Hayworth), but when he loses his chance with her, he “settles” for her friend. Rita Hayworth died her hair red for this film and it became her trademark.

An outmoded, silly convention started by the cavemen and encouraged by the florists and jewelers. After all, what’s marriage?” — Amy Lind

1. The Adventures of Robin Hood (1938) — Errol Flynn, Olivia de Havilland, Basil Rathbone, Claude Rains, and Alan Hale star in this classic telling of a classic legend.

Almost every telling of the Robin Hood story, since this one, has sought a fresh take, trying to deconstruct or be revisionist, trying to adapt the story to the times. This telling says “screw that” and just goes for full up swashbuckling adventure; Howard Pyle rendered in technicolor.

He won’t. He’ll stick your funny head on London’s Gate.” — Marian

What would make your list?

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