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Top 10 Olivia De Havilland Films

Lindsay is a working actress and honors graduate of Texas Christian University with a Bachelor of Fine Arts degree in Theatre: Film/TV.

Who Was Olivia De Havilland?

Olivia De Havilland stumbled into movies practically by accident. Discovered by director Max Reinhardt while performing in a community college production of A Midsummer Night’s Dream, this event ultimately led to a starring role in the successful 1935 film version of the play and inevitable Hollywood stardom.

But, one can not talk about Olivia De Havilland without mentioning her most frequent co-star, Errol Flynn. Flynn and Olivia formed one of Hollywood’s most beloved screen teams and you’ll find four of their eight films together on this list. Behind the scenes, the two stars harbored very real feelings for one another, greatly amplifying their chemistry onscreen (in real life, their mutual crushes never quite moved past friendship). Today Olivia is best remembered for her roles as good girls and damsels-in-distress, but, in reality, her acting range was much wider, earning her two Academy Awards and an impressive five nominations.

But, Olivia’s greatest legacy, actually, occurred off-screen. When she successfully sued Warner Bros for extending her contract past seven years, it resulted in the establishment of the “De Havilland Law”. The landmark ruling granted actors with greater creative freedom and lessened the almighty powers of the studios. “The De Havilland Law” remains a ubiquitous tenant of entertainment law to this very day. So, whether they know it or not, every entertainer in Hollywood owes a debt to the lovely Olivia.

Top 10 Olivia De Havilland Films

  1. Gone With The Wind
  2. The Heiress
  3. The Adventures of Robin Hood
  4. Captain Blood
  5. The Snake Pit
  6. The Strawberry Blonde
  7. Hush...Hush, Sweet Charlotte
  8. They Died With Their Boots On
  9. The Proud Rebel
  10. The Charge of the Light Brigade

1. Gone With the Wind (1939)

Based on the Pulitzer Prize-winning book by Margaret Mitchell, this iconic romantic epic is considered by many to be one of the greatest films ever made. It chronicles the journey of spoiled Southern belle Scarlett O’Hara (Vivien Leigh) as she lives through the death of the old South, from the brutality of the Civil War to the just-as-turbulent Reconstruction. However, the true driving force of this film is the tortured love triangle (or, more accurately, love square) between Scarlett, the man she’s long held a torch for, Ashley Wilkes (Leslie Howard), Ashley’s fiancée, Melanie Hamilton (Olivia), and the roguish Rhett Butler (Clark Gable), who has developed a particular fascination with the fiery Scarlett. Featuring an iconic score by Max Steiner and powerful visuals that have since become legendary, Gone With the Wind comes pretty close to being a perfect film. Although Olivia's role as Melanie is, technically, just a supporting role, it is, nevertheless, the role she will forever be remembered for. The compassionate and selfless Melanie provides a perfect counterpoint to the more self-serving Scarlett. Unlike most Hollywood starlets at the time (who were fighting to play Scarlett), Olivia only had eyes for the role of Melanie and fought for Warner Bros to let her out of her contract in order to play her. Gone With The Wind became the first color film to win a Best Picture Oscar and walked away with 10 Academy Awards in total (a record that wouldn’t be beaten until 1960). Be forewarned that this film is very long, clocking in at over 3 ½ hours, but, honestly, this movie is so jam-packed that it’s unlikely you’ll even notice. In fact, the original preview audience begged the filmmakers not to cut it any shorter. Gone With The Wind is the definition of a film in which not a single frame is wasted.

2. The Heiress (1949)

Based on the Broadway play of the same name (which is, itself, an adaptation of Henry James’ novel, Washington Square), The Heiress is best described as a human tragedy filled with bitter irony. Set in the mid-1800s, the movie stars Olivia as Catherine Sloper, a shy and awkward girl who has been raised entirely by her rich and emotionally distant father, Dr. Austin Sloper. Dr. Sloper makes no secret of his disappointment in Catherine’s inability to live up to the memory of her beautiful and vivacious mother, continually crushing the poor girl's self-esteem. So when a handsome newcomer named Morris Townsend (Montgomery Clift) begins to show an interest in Catherine, it brings untold happiness to the lonely girl’s life. But, it, also, raises her father’s suspicions. He's convinced that Morris is only interested in Catherine’s very large inheritance, a prize he is determined to keep out of the young man’s reach at any cost (even if it means destroying his daughter’s chance at happiness in the process). Olivia gives a stunning performance as the awkward Catherine, growing into a very different woman by the film’s almost chilling finish. The talented Montgomery Clift is, also, perfectly cast as Morris: handsome and charming, yet unreadable in a suspicious and subtle way. But, behind the scenes, Olivia and Clift did not get along at all. A trained Method actor, Clift had very little respect for Olivia’s more classical acting process and was not afraid to show it. Luckily, Olivia had personally selected William Wyler as the film’s director. Wyler looked out for Olivia and stood up for her when needed, providing her with the confidence to give one of the defining performances of her career (earning herself an Oscar for Best Actress in the process).

3. The Adventures of Robin Hood (1938)

This rousing action film retells the famous Robin Hood legend on a grand scale, full of bright and colorful pageantry. In fact, it took every Technicolor camera in existence to film it. The film stars Olivia as the willful and intelligent Lady Marian and Errol Flynn in his definitive portrayal as the roguish Robin Hood. The movie follows Robin as he makes his transition from Saxon knight to outlaw, forming his band of Merry Men and defying the wicked Prince John (Claude Rains) by daring to rob from the rich and give to the poor. Yet, all the while, Robin remains eternally loyal to the kingdom’s true king, King Richard. The most iconic moment from The Adventures of Robin Hood is the epic duel between Errol Flynn’s Robin and Basil Rathbone’s Sir Guy of Gisbourne, considered by many to be one of the greatest (and certainly most famous) swordfights in movie history. As for Robin Hood’s iconic archery, the most difficult shots were performed by professional archer Howard Hill. Hill, also, helped the sound department develop the movie’s distinctive “arrow sound”, achieved by using oversized arrows. Years later, these recordings were used again by sound designer Ben Burtt, who has since named it as his favorite sound (using it in most of the Star Wars films and nearly every film he has worked on since).

4. Captain Blood (1935)

Based on the very successful novel by Rafael Sabatini, Captain Blood is the film that turned Olivia and Errol Flynn into instant stars, creating one of cinema’s most successful screen partnerships. Set in the 17th century, the film follows the story of Peter Blood (Flynn), a noble doctor who is wrongfully arrested for treason and sent to Jamaica as a slave. Olivia plays the part of Arabella Bishop, a wealthy citizen of Port Royal who takes a liking to Peter after he dares to stand up to her cruel uncle’s prodding. She convinces her uncle to buy Peter despite his defiant attitude, but Peter is not nearly as grateful as Arabella may have hoped. In fact, he is so intent on escaping his bondage in any way possible, that no matter how many favors she tries to do for him, Peter merely rewards Arabella with continued resentment for his subservient status. But when a band of pirates attack the city, it just might be Peter Blood’s lucky break. Captain Blood marked Errol Flynn’s very first starring role, but the way he manages to command every scene makes that hard to believe. Behind the scenes, sparks flew immediately when Olivia met Flynn for the first time and their mutual attraction is palpable on screen. This movie was immensely popular when first released, causing something unprecedented to occur when it came time to vote for the Academy Awards. Although director Michael Curtiz, screenwriter Casey Robinson, and composer Erich Wolfgang Korngold, were not nominated for their work on the film, all three received enough write-in ballots to bypass most of the actual nominees. Robinson and Korngold each ranked third in the final ballots, but Curtiz, actually, came in second in the final tally (barely losing out to winner John Ford). If that's not a solid recommendation for the work done in this movie, I don’t know what is.

5. The Snake Pit (1948)

Adapted from the book by Mary Jane Ward, The Snake Pit tells the harrowing story of Virginia Cunningham (Olivia), a woman who finds herself locked in an insane asylum with no memory of how she got there. Now Virginia must fight to regain her sanity within the walls of a mental hospital that seems to be more concerned with regulations than the patients’ wellbeing. Her only ally is a psychiatrist everyone refers to as “Dr. Kik”, a compassionate and forward-thinking man who believes that psychoanalysis is the key to Virginia’s cure rather than the more “conventional” procedures. This film proved to be a great opportunity for Olivia, who gives one of her most realistic and raw performances as Virginia, a woman struggling for sanity while being unable to remember exactly what that means. Director Anatole Litvak insisted that the entire cast and crew prepare for filming by undergoing three months of intensive research, including visits to various mental hospitals and lectures by leading psychiatrists. However, Olivia didn’t stop there and did even more research on her own time. This included sitting in on electro-shock and hydrotherapy treatments, attending some of the patients’ social functions, and even observing individual psychotherapy sessions (when permitted). Undoubtedly, her research paid off and the impact of The Snake Pit was more than artistic. The film has been credited with opening the public’s eyes to the indifferent treatment of mental patients in insane asylums, resulting in widespread changes in the conditions of mental institutions across the country.

6. The Strawberry Blonde (1941)

Directed by Raoul Walsh, this light nostalgic movie is based on the play, One Sunday Afternoon by James Hagan. The play had already been (unsuccessfully) made into a movie once before in the '30s, but a major change made for this adaptation was moving the setting from a small Mid-West town to the bustling city of New York. This change allowed for the casting of non-traditional leading man Jimmy Cagney, a brilliant move that pays off in spades. Set in the 1890s, the movie stars Cagney as Biff Grimes, a dental student hopelessly in love with the local coquette, Virginia Brush (played by Rita Hayworth). But, Biff’s love goes unrequited as his so-called “friend”, Hugo, keeps stealing Virginia away from him. Instead, Biff is continually forced to spend time with Virginia’s best friend, Amy (Olivia). Although he, eventually, settles for a life with the less glamorous Amy, Biff continues to hold a torch for the one that got away. So when Biff gets a chance to, finally, get even with the unscrupulous Hugo, will he do it? Produced by Cagney’s brother William, The Strawberry Blonde was intended as a nostalgic gift to the Cagneys’ aging mother and, indeed, the 1890s have never looked more charming. Olivia adored working with Raoul Walsh, whom she respected enormously and her enjoyment is obvious onscreen. She is absolutely adorable as the intelligent and (slightly) rebellious Amy. But, you can’t talk about this movie without mentioning the titular “Strawberry Blonde”, Rita Hayworth. Actually, The Strawberry Blonde is the film responsible for Hayworth's iconic red hair. Originally, it was assumed that her hair would be dyed back to its natural black after filming, but the red hair suited the actress so well that Hayworth wound up retaining it for the majority of her career.

7. Hush . . . Hush, Sweet Charlotte (1964)

Made to capitalize on the success of What Ever Happened To Baby Jane, this Grand Guignol-style film pairs Olivia with both the star and director of Baby Jane: Bette Davis and Robert Aldrich (respectively). It tells the story of Charlotte Hollis (Davis), a wealthy New Orleans spinster whom many believe to be crazy. As a young woman, she had an affair with a married man and her lover was mysteriously (and brutally) murdered the day he tried to break up with her. The murder has since become town legend and most believe Charlotte to be the killer. Unstable and fragile, Charlotte has never left her childhood home and even after receiving an eviction notice from the Louisiana Highway Commission, she refuses to leave. Looking for help, she contacts her cousin, Miriam (Olivia), and Miriam quickly decides to stay with her troubled cousin until the inevitable move. But, Charlotte’s mental health seems to be deteriorating rapidly. Is Charlotte really crazy, or is something else going on in that house? Originally, the role of Miriam was written with Joan Crawford in mind, but Crawford bowed out after contracting pneumonia (however, many speculate that the real reason was Bette Davis' hostile attitude towards her). In a brilliant piece of casting, Olivia was brought in late into the production and gives a perfectly layered and restrained performance as Miriam. She, also, provided the character with a gentle elegance completely absent from the original script. Olivia and Davis were good friends and their mutual respect for one another made the rest of the shoot go by very pleasantly. Now regarded as a cult classic, Hush, Hush, Sweet Charlotte is surprisingly effective dramatically, filled with great cinematography and first-rate performances that should not be missed.

8. They Died With Their Boots On (1941)

Directed by Raoul Walsh, They Died With Their Boots On is a highly fictionalized and romanticized version of the life of George Armstrong Custer. The film starts off with his first day at West Point and goes all the way up to his infamous Last Stand at Little Bighorn. Basically, if you’re looking for the true life story of General Custer, you best walk away now. However, if you’re just looking for a good story, than you’ve come to the right place. This is a beautiful movie and it’s easy to forget any prejudices you may have harbored against the real Custer within the first half hour. The film’s version of Custer (played by Errol Flynn) is brash, careless, and impatient to a fault, but, also, extremely charismatic. Interestingly, the film starts out in an almost comedic tone and grows gradually darker as the story goes on. Flynn, actually, gives one of his best performances in They Died With Their Boots On, as we watch Custer grow from an incompetent and impetuous youth into a man of true nobility and strength of character. Olivia plays the part of Elizabeth “Libby” Bacon, Custer’s great love and eventual wife, who desires nothing more than for her husband to put down his sword forever, and yet is still willing to sacrifice anything for his happiness. Olivia gives a wonderful and subtle performance as Libby and the film’s sumptuous Civil War era gowns suit her beautifully. This film ended up being the last Olivia and Flynn would make together and their chemistry has never been more potent. Appropriately, the last scene the two shot together was the scene in which George and Libby say their final goodbyes.

9. The Proud Rebel (1958)

Directed by Olivia’s frequent collaborator, Michael Curtiz, this lesser known Western stars Alan Ladd as John Chandler, a former Confederate soldier whose wife was killed in a house fire during the war. John’s son, David, was a witness to his mother’s death and hasn’t uttered a word since that day. Hoping to find a cure for his son’s condition, John has traveled with David from town to town and doctor to doctor with no results. While passing through Illinois, John gets into a scuffle with an unscrupulous rancher that results in John being arrested. Local farmer Linnett Moore (Olivia) takes pity on the young David and agrees to pay his father’s fine as long as John works it off as a farmhand. Up until now, Linnett has been satisfied with her independent, yet solitary, existence as lone inhabitant of her family's aging farm, but the sudden presence of John and David may just be enough to change her mind. The tough and strong-willed Linnett in a far cry from many of Olivia’s most iconic roles and she pulls off the part beautifully. But, you can’t really talk about The Proud Rebel without mentioning David Ladd (Alan Ladd’s real-life son), who gives a miraculously realistic and heartfelt performance as the mute David Chandler. The chemistry between Ladd and his real-life son is palpable, giving extra emotional weight to their interactions. The Proud Rebel is a great family film and one deserving of far more recognition than it gets.

10. The Charge of the Light Brigade (1936)

Loosely based on historical events, The Charge of the Light Brigade even goes so far as to open with a disclaimer that clarifies that the interpretation is highly fictionalized. Actually, this film is based, primarily, on the poem of the same name by Alfred Lord Tennyson. The film once again reunites Olivia with frequent co-star, Errol Flynn and her Captain Blood director, Michael Curtiz. However, the dynamics between Olivia and Errol’s characters are very different from most of the movies they did together. Set in the 1850s, the film stars Flynn as Captain Geoffrey Vickers, a member of the British Army’s 27th Lancers who has been stationed in India for some time. While he’s been away on duty, Geoffrey’s fiancée, Elsa (played by Olivia), has fallen in love with his brother, Perry (also, a member of the British army). Geoffrey remains blissfully ignorant of this turn of events and both parties are terrified to tell him. Meanwhile, a former ally of the British government, tribal leader Surat Khan, has turned on Britain and taken Russia’s side at the onset of the Crimean War. The British government is hesitant to break the peace they’ve long maintained with Surat Khan’s people, but the headstrong monarch may be more bloodthirsty than anyone thought possible. Naturally, the major set piece of this film is the titular “charge of the light brigade”. The charge is an epic and overwhelming scene unlike anything that’s likely to be seen onscreen again, full of life-threatening stunts that will take your breath away. However, this dangerous sequence came at a high cost, resulting in the deaths of dozens of stunt horses and one stuntman. The carnage prompted Congress to intervene and new laws were passed to ensure the safety of animals in film from that moment onward.

Honorable Mention: Light in the Piazza (1962)

For my honorable mention, I have chosen this sweetly romantic tale, based on the novella by Elizabeth Spencer. Light in the Piazza stars Olivia as American tourist Meg Johnson, who is vacationing in Italy with her beautiful, but mentally impaired, daughter, Clara (played by Yvette Mimieux). While traveling, they meet a young man named Fabrizio (George Hamiltion), who takes an immediate romantic interest in Clara. Fabrizio and his wealthy Italian family absolutely adore the girl's charmingly naïve and childlike nature, completely unaware of her actual mental limitations. This new relationship puts Meg in an ethical quandary. Should she tell Fabrizio about Clara’s condition and risk her daughter’s heart being broken? Meg’s husband, Noel, is convinced that the boy and his family deserve to know. He, also, has been strongly suggesting that Clara be put into a home now that she’s older. Meg worries that life with Fabrizio might be Clara’s last chance at a normal life and if her disability is revealed, it could disappear forever. Shot on location in Rome and Florence, Light in the Piazza features gorgeous images of Italy, perfectly complimenting the film’s romantic tone. Olivia gives a realistic and sensitive performance as a mother desperate to do what’s right for her child, but struggling with what that might be. In 2005, Light in the Piazza was adapted into a successful Broadway musical, which has become even more famous than this gem of a movie. Before seeing it on stage, I highly recommend seeing this film first, if for no other reason than to see this story told among the genuine wonders of 1960s Italy.

Further Reading

If you would like to learn more about the lovely Olivia De Havilland, please read Victoria Amador's recent biography, Olivia De Havilland: Lady Triumphant (2021), as well as Olivia's own delightful memoir, Every Frenchman Has One (1962).

© 2013 Lindsay Blenkarn


Lindsay Blenkarn (author) from Nashville, TN on August 08, 2017:

@Robert E.

Yeah, I was surprised that LIBEL and DARK MIRROR didn't make the list as well. But, their ratings on Netflix, IMDB and Rotten Tomatoes at the time I wrote this just weren't high enough to make the list. :( However, a lot of Olivia's movies have recently become more readily available and therefore, had a nice boost in popularity (mostly thanks to streaming channels). Actually, out of curiosity, I recently rechecked my "algorithm" (or whatever you wanna call it) for my Olivia list to see if anything had changed. The ones at the top of the list pretty much stayed the same but, a few of the ones lower on the list did get moved around or replaced. But, even with that, LIBEL and DARK MIRROR still didn't quite make the top 10. It was very close though! Just too many good movies to choose from, apparently! :)

Robert E. on August 08, 2017:

I'm quite surprised not to see LIBEL and THE DARK MIRROR on Every Olivia Best List, near the top!

Tyya on January 25, 2015:

Tip top stfuf. I'll expect more now.

Lindsay Blenkarn (author) from Nashville, TN on February 15, 2013:

Thanks for checking out my list! I hope it helped you learn a little bit more about Olivia De Havilland. The stories I've read about her (particularly those involving her relationships with Errol Flynn or her sister, Joan Fontaine) have been very interesting so, I'm sure that book you have will make a nice read. "Robin Hood" is definitely a classic and Basil Rathbone is great! That's the thing I love about Rathbone. He makes the best villain yet he was, also, capable of being a great leading man. He will always be the definitive Sherlock Holmes to me too. Ironic how an actor who played so many bad guys ended up becoming most famous for playing one of literature's greatest heroes! (BTW, Rathbone, also, makes an appearance in "Captain Blood" with De Havilland and Flynn so, if you haven't already, you may want to check that movie out as well!)

Rich from New Jersey on February 14, 2013:

While I don't know that much about De Havilland, I always liked her.... I've had a book about her for many years, I just never got around to reading it, maybe I should give it a try. Also, I love Robin Hood, mostly for Basil Rathbone. It's one of the best bad guys ever. Oddly enough, I think he was also the best Sherlock Holmes, too.