Top 10 Films: Olivia de Havilland
- Lindsay Blenkarn
- Jul 6
- 15 min read
Updated: Aug 2
Dame 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. Today, Dame 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, one cannot talk about Olivia de Havilland without mentioning her most frequent co-star, Errol Flynn. Flynn and de Havilland formed one of Hollywood’s most beloved screen teams of the 1930s and '40s. Behind the scenes, the two stars harbored very real feelings for one another, greatly amplifying their chemistry onscreen. But in real life, their mutual crushes never quite moved past friendship.
Yet, 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”. This landmark ruling granted actors greater creative freedom and lessened the almighty powers of the studios. And the "De Havilland Law" still remains a ubiquitous tenet of entertainment law to this very day. In 2009, the De Havilland Law actually helped the band Thirty Seconds to Mars get out of their contract with music label EMI, prompting frontman Jared Leto to thank Olivia personally afterwards for helping to establish this important precedent. Whether they know it or not, every single entertainer in Hollywood owes a debt to the lovely Olivia. But, which of Olivia de Havilland's movies still remain the most popular in 2026...??
10. In This Our Life (1942)
Based on the Pulitzer Prize-winning novel by Ellen Glasgow and directed by John Huston, In This Our Life is the 3rd of 5 movies Olivia de Havilland made with her friend Bette Davis. In the movie, Olivia and Bette play the roles of the Timberlake sisters. Roy Timberlake (Olivia) is a successful interior decorator and married to a doctor named Peter. Meanwhile, Stanley Timberlake (Bette Davis) is engaged to a successful attorney named Craig. But, the day before Stanley and Craig's wedding, Stanley suddenly runs off with Peter instead, leaving both Roy and Craig heartbroken. After Roy and Peter’s divorce is finalized, Peter marries Stanley. But, married life with Peter does not exactly turn out the way that Stanley had hoped. And so, just as Roy and Craig are starting to put their lives back together, the self-absorbed Stanley is right on cue to shake things up once again. Except this time, Craig and Roy’s feelings may not be the only casualties.
During production of In This Our Life, Olivia de Havilland was, actually, having a not-so-secret affair with director John Huston. The head of Warner Bros., Jack Warner, joked that “it was Valentine’s Day on the set, Bette has the lines, but Livvie is getting the best camera shots.” John Huston’s desire to stay close to Olivia was, actually, one of the main reasons he agreed to direct In This Our Life in the first place. The movie was only Huston’s 2nd time directing a feature film and, unfortunately, he didn’t even get to finish it. After the attack on Pearl Harbor, John Huston ended up being called away on a war assignment and director Raoul Walsh was called in to finish the film. Unfortunately, Bette Davis did not get along with Raoul Walsh at all, to the point that Walsh actually threatened to quit and the movie’s producer, Hal Wallis, had to frequently come in to mediate.
When In This Our Life was first released, it actually ended up being barred from being shown internationally by the wartime Office of Censorship. This was because a major part of the movie’s plot ends up dealing with the issue of racial discrimination. The film’s studio, Warner Bros., was even added to The Honor Roll of Race Relations of 1942 because of the movie’s sensitive portrayal of racial issues.
9. To Each His Own (1946)
The film that won Olivia de Havilland her first Oscar for Best Actress, To Each His Own was actually her first film in 3 years, after her landmark suit against Warner Bros. made her a bit of a pariah to the Hollywood studio heads. But, it was Paramount Pictures that finally gave her this triumphant return to the screen. Olivia plays the role of Josephine "Jody" Norris, a small town girl who works in her father's drugstore during World War I. One day, an Army fighter pilot named Captain Bart Cosgrove comes into town to promote war bonds and the two fall madly in love. Although they only have one night together, Jody and Bart keep in touch when he goes back to the front. Not long after Bart leaves, Jody realizes that she's pregnant. However, this seems to be a moot point at first since, due to a medical complication, her doctor recommends her for a surgery that will save her life but, cause her to lose the baby.
But, Jody decides to take the risk when she learns that Bart has been killed in action, leaving their baby as the last remaining piece of him. She manages to survive the birth but, to protect her newborn son from small town gossip, she comes up with a plan that she hopes will hide the circumstances of his birth from the rest of the town. But, her elaborate plan does not go nearly as well as she'd hoped and Jody will be forced to deal with the consequences of this choice for years to come.
The bulk of this film is actually told in flashback so, we are first introduced to Jody as a middle-aged woman. The subtle aging makeup and lighting effects used are extremely well done and Olivia's Oscar-winning performance makes the illusion that we actually watch Jody age from her 20s to her 40s complete (in reality, Olivia was 30 at the time). Extra Fun Fact: the aircraft Bart flies is specified to be a DH, short for De Havilland. This is a reference to Olivia's real-life cousin, Sir Geoffrey de Havilland, who was a pioneering aviation engineer and founder of the revolutionary De Havilland Aircraft Company.
8. It's Love I'm After (1937)
Probably the most surprising movie to make it into this top 10, this screwball comedy was the very first movie Olivia de Havilland made with Bette Davis and it’s definitely the most fun. Based on the short story Gentlemen After Midnight by Maurice Hanlin, it stars Leslie Howard and Bette Davis as Basil Underwood and Joyce Arden. Basil and Joyce are both respected theatre actors and have been engaged in a stormy on-again off-again romantic relationship for quite some time. They’re in a constant loop of getting engaged, having a fight, calling it off, and then making up again. After a performance of Romeo and Juliet ends with yet another one of their squabbles, Basil goes back to his dressing room and is surprised by a fan named Marcia (Olivia), who has snuck backstage to meet him. Basil offers Marcia an autograph or a picture but, she politely refuses. Instead, she merely gives a heartfelt declaration of love for him and quietly disappears into the night, leaving Basil charmed and flattered. Despite the speech she just gave to Basil, Marcia actually already has a fiancé, named Henry. Henry is understandably concerned about his fiancée’s devotion to Basil and decides he must find a way to stifle this infatuation. And possibly the best way to do that is to enlist the help of Basil, himself.
When Leslie Howard first signed on to make It’s Love I’m After, it was originally imagined that the role of Joyce would be played by either Gertrude Lawrence or Ina Claire, both highly respected stage actresses with a lot of experience with comedic roles. However, since neither of them had very much experience on film, the movie’s producer, Hal Wallis, decided that the role of Joyce might be a really good change of pace for Bette Davis, who had become much more well-known for her dramatic roles. Leslie Howard and Bette Davis had been paired up in 2 other movies before this one but, It’s Love I’m After actually ended up being the very last film they would appear in together (as well as their only comedy).
At first, Bette Davis was hesitant to take the role of Joyce since she considered Olivia’s role of Marcia the better part. She also didn’t like getting 2nd billing under Leslie Howard. So, to convince her to take the role, Hal Wallis agreed to replace the movie’s cinematographer, James Van Trees, with one that Davis already trusted could photograph her well (Tony Gaudio). Despite this, only Van Trees was officially given credit for his work on the film.
7. Hold Back the Dawn (1941)
Based on the novel by Ketti Frings, Hold Back the Dawn stars Olivia de Havilland opposite Charles Boyer. Boyer plays the role of Georges Iscovescu, a Romanian con man living in Mexico after fleeing the Nazi occupation in Europe. Georges originally came to Mexico in the hopes that he would easily be able to immigrate into the US from there. However, it turned out that according to America’s immigration quota system, Georges is required to wait 5 to 8 years before he can gain entry into the US. So, in the meantime, he has been unhappily waiting it out in Tijuana. But, when Georges runs into an old girlfriend who has just gotten her American citizenship by marrying an American, he immediately makes marrying an American citizen his new plan. He sets his sights on Emmy Brown (Olivia), a naive schoolteacher from California who is visiting Mexico with her students for a field trip. Although Georges only has a limited time to seduce Emmy before she has to return back to the States with her students, he manages to win her over and his plan to catch an American wife seems to be working. But, Emmy is nothing like the women Georges usually deals with and his plan to abandon her shortly after their marriage may not work out quite as simply as he thought.
The screenplay for Hold Back the Dawn was actually co-written by legendary writer/director Billy Wilder. While Wilder would later go on to have great success writing & directing his own films, Hold Back the Dawn was one of the very last screenplays he ever wrote that he didn’t direct himself. Some have even claimed that it was Wilder’s disagreement with Hold Back the Dawn director Mitchell Leisen’s directorial choices that inspired him to focus on directing his own films. Incidentally, Mitchell Leisen actually has a cameo in this film as himself (he even joined the Screen Actors Guild in order to do it). He’s seen directing a rehearsal scene from another movie he directed (I Wanted Wings) with actress Veronica Lake, also, appearing in a cameo as herself.
Olivia’s performance in Hold Back the Dawn earned her an Oscar nomination for Best Actress, marking her very first time being nominated in the Lead Actress category. Coincidentally, Olivia’s sister, Joan Fontaine, was also nominated that year, making it the very first time a pair of siblings had ever been nominated in the same category. The sisters were known for having a stormy relationship with one another so a lot of press was made about the face-off. In the end, it was Joan who ultimately won the Oscar for her performance in the movie Suspicion.
6. The Snake Pit (1948)
Adapted from the book by Mary Jane Ward, The Snake Pit tells the harrowing story of Virginia Cunningham (Olivia de Havilland), 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 well-being of its patients. Virginia's only ally is a psychiatrist everyone refers to as “Dr. Kik”, a compassionate and forward-thinking man who believes that psychoanalysis is the solution, rather than the more “conventional” procedures.
The Snake Pit was a great opportunity for Olivia, who gives a realistic and raw performance 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. Olivia 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.
5. Captain Blood (1935)
Based on the very successful novel by Rafael Sabatini, Captain Blood is the film that turned Olivia de Havilland and Errol Flynn into instant stars, creating one of classic Hollywood'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. Arabella convinces her uncle to buy Peter despite his defiant attitude, but Peter is not nearly as grateful as she hoped. In fact, he is so intent on escaping his bondage that no matter how many favors she does for him, Peter rewards Arabella with resentment for his continued subservient status. However, when a band of pirates attacks the city, it might be Peter’s lucky break.
Captain Blood was Errol Flynn’s breakout role and seeing the way he commands every scene, it's easy to understand why. Behind the scenes, sparks flew immediately when Olivia de Havilland met Flynn for the first time and their mutual attraction is palpable on screen. Captain Blood ended up being immensely popular with both fans and critics. In fact, even though director Michael Curtiz, screenwriter Casey Robinson, and composer Erich Wolfgang Korngold weren't even nominated for Academy Awards, all three received enough write-in ballots to bypass most of the actual nominees! Robinson and Korngold both ranked third in the final ballots, while Curtiz just barely lost to the actual Best Directing winner, John Ford.
4. 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 de Havilland with both the star and director of Baby Jane: Bette Davis and Robert Aldrich, respectively. The movie 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 he was mysteriously (and brutally) murdered after trying 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), who quickly decides to stay with her troubled cousin until the inevitable move. Charlotte’s mental health seems to be deteriorating rapidly. But, is Charlotte really crazy, or is something else going on in that house?
The role of Miriam was originally written with Joan Crawford in mind, but Crawford bowed out after contracting pneumonia (though 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 she gives a perfectly layered and restrained performance as Miriam. She provides the character with a gentle elegance completely absent from the original script. Davis and de Havilland were very good friends in real-life and their mutual respect made the rest of the shoot go by without a hitch. Now regarded as a cult classic, Hush...Hush, Sweet Charlotte is a surprisingly effective drama filled with great cinematography and fantastic performances.
3. The Heiress (1949)
Based on the Broadway play of the same name (itself an adaptation of Henry James’ 1880 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 de Havilland as Catherine Sloper, a shy and awkward girl raised entirely by her rich, 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) shows 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 de Havilland gives a stunning performance as the awkward Catherine, growing into a very different woman by the film’s finish. The talented Montgomery Clift is also perfectly cast as Morris: handsome and charming, yet unreadable in a suspicious and subtle way. Behind the scenes, de Havilland 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 an Oscar for Best Actress in the process).
2. 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 at the time to film it. The Adventures of Robin Hood stars Olivia de Havilland as the willful and intelligent Maid 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. All the while, Robin remains eternally loyal to England's one true king, Richard I (aka Richard the Lionheart).
The most iconic moment from The Adventures of Robin Hood is the epic sword fight 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) sword fights 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 by developing the movie’s distinctive “arrow sound”, achieved by using oversized arrows. Years later, these arrow recordings were actually used in the Star Wars films, with sound designer Ben Burtt even naming it as his favorite sound in movie history.
1. Gone With the Wind (1939)
And, of course, there was no other choice for number one. Based on the Pulitzer Prize-winning book by Margaret Mitchell, this iconic romantic epic is still 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, Ashley Wilkes (Leslie Howard), Ashley’s fiancée, Melanie Hamilton (Olivia de Havilland), 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, supporting, it is nevertheless the role for which she'll be forever remembered. The compassionate and selfless Melanie provides a perfect counterpoint to the self-serving Scarlett. Unlike most Hollywood starlets at the time that were fighting to play Scarlett, Olivia only had eyes for the role of Melanie and fought Warner Bros. to let her out of her contract for the role. Gone With The Wind became the very first color film to win a Best Picture Oscar and it 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 it's so jam-packed that it’s unlikely you’ll notice. In fact, the original preview audience begged the filmmakers not to cut it any shorter because, Gone With The Wind is the definition of a film in which not a single frame is wasted.
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 de Havilland as American tourist Meg Johnson, vacationing in Italy with her beautiful mentally impaired daughter, Clara (Yvette Mimieux). While traveling, they meet a young man named Fabrizio (George Hamilton), 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 or allow their relationship to continue unhindered?
Meg’s husband, Noel, is convinced that the boy and his family deserve to know. But, he has, also, implied that Clara should be put into a home now that she’s older. Meg worries that life with Fabrizio might be her daughter's last chance at a "normal" life. If her disability is revealed, that chance could disappear forever.
Shot on location in Rome and Florence, Light in the Piazza showcases gorgeous images of Italy, perfectly complementing 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 since become even more famous than this gem of a movie. But, before seeing it on stage, I highly recommend seeing the original film first. If for no other reason than just to see the genuine wonders of 1960s Italy.
To see this list on Letterboxd: https://boxd.it/z7GZK$3gNCPOM1sCc9x0hd
Which Olivia de Havilland Movie Is Your Favorite?
Gone with the Wind
It's Love I'm After
In This Our Life
Light in the Piazza
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