At 104 years old, Olivia de Havilland has this physical status:
De Havilland made her screen debut in Reinhardt's A Midsummer Night's Dream, which was filmed at Warner Brothers studios from December 19, 1934, to March 9, 1935. During the production, de Havilland picked up film acting techniques from the film's co-director William Dieterle and camera techniques from cinematographer Hal Mohr, who was impressed with her questions about his work. By the end of filming, she had learned the effect of lighting and camera angles on how she appeared on screen and how to find her best lighting. Following premieres in New York City and Beverly Hills, the film was released on October 30, 1935. Despite the publicity campaign, the film generated little enthusiasm with audiences. While the critical response was mixed, de Havilland's performance was praised by The San Francisco Examiner critic. In his review in the Brooklyn Daily Eagle, Winston Burdett wrote that she "acts graciously and does greater justice to Shakespeare's language than anyone else in the cast". Two minor comedies followed, Alibi Ike with Joe E. Brown and The Irish in Us (both 1935) with James Cagney. In both films, she played the sweet and charming love interest—a role into which she would later become typecast. After the experience of being a Reinhardt player, de Havilland felt disappointed being assigned these routine heroine roles. In March, de Havilland and her mother moved into an apartment at the Chateau des Fleurs at 6626 Franklin Avenue in Hollywood.
Although Warner Brothers studio had assumed that the many costumed films that studios such as MGM had earlier produced would never succeed during the years of the American Great Depression, they nonetheless took a chance by producing Captain Blood (also 1935).: 63 The film is a swashbuckler action drama based on the novel by Rafael Sabatini and directed by Michael Curtiz.: 63 Captain Blood starred a then little-known contract bit-part actor and former extra, Errol Flynn, with the equally little-known de Havilland. According to film historian Tony Thomas, both actors had "classic good looks, cultured speaking voices, and a sense of distant aristocracy about them". Filmed between August 5 and October 29, 1935, Captain Blood gave de Havilland the opportunity to appear in her first costumed historical romance and adventure epic, a genre to which she was well suited, given her beauty and elegance. In the film, she played Arabella Bishop, the niece of a Jamaica plantation owner who purchases at auction an Irish physician wrongly condemned to servitude. The on-screen chemistry between de Havilland and Flynn was evident from their first scenes together, where clashes between her character's spirited hauteur and his character's playful braggadocio did not mask their mutual attraction to each other. Arabella is a feisty young woman who knows what she wants and is willing to fight for it. The bantering tone of their exchanges in the film—the healthy give-and-take and mutual respect—became the basis for their on-screen relationship in subsequent films. Captain Blood was released on December 28, 1935, and received good reviews and wide public appeal. De Havilland's performance was singled out in The New York Times and Variety. The film was nominated for four Academy Awards, including Best Picture. The popular success of the film, as well as the critical response to the on-screen couple, led to seven additional collaborations: The Charge of the Light Brigade (1936), The Adventures of Robin Hood (1938), Four's a Crowd (1938), Dodge City (1939), The Private Lives of Elizabeth and Essex (1939, although de Havilland played a supporting role with Bette Davis as Flynn's leading lady), Santa Fe Trail (1940), and They Died with Their Boots On (1941).
De Havilland appeared in Mervyn LeRoy's historical drama Anthony Adverse (1936) with Fredric March. Based on the popular novel by Hervey Allen, the film follows the adventures of an orphan raised by a Scottish merchant whose pursuit of fortune separates him from the innocent peasant girl he loves, marries, and eventually loses. De Havilland played a peasant girl, Angela, who after being separated from her slave-trader husband becomes opera star Mademoiselle Georges, the mistress of Napoleon. The film earned six Academy Award nominations, including Best Picture. It garnered de Havilland good exposure and the opportunity to portray a character as she develops over time. Howard Barnes of the New York Herald Tribune found her later scenes as Mademoiselle Georges "not very credible", but Frank S. Nugent of The New York Times called her "a winsome Angela". That same year, she was re-united with Flynn in Michael Curtiz's period action film The Charge of the Light Brigade (also 1936), featuring Flynn look-alike Patric Knowles (playing Flynn's brother) and David Niven. The picture was set during the Crimean War and became a major box office hit.
During the film's production, de Havilland renegotiated her contract with Warner Bros. and signed a seven-year contract on April 14, 1936, with a starting weekly salary of $500 (equivalent to $9,800 in 2021). Toward the end of the year, 20-year-old de Havilland and her mother moved to 2337 Nella Vista Avenue in the Los Feliz section of Los Angeles.
De Havilland had her first top billing in Archie Mayo's comedy Call It a Day (1937), about a middle-class English family struggling with the romantic effects of spring fever during the course of a single day. De Havilland played daughter Catherine Hilton, who falls in love with the handsome artist hired to paint her portrait. The film did not do well at the box office and did little to advance her career.
She fared better in Mayo's screwball comedy It's Love I'm After (also 1937) with Leslie Howard and Bette Davis. De Havilland played Marcia West, a debutante and theatre fan enamoured with a Barrymore-like matinee idol who decides to help the girl's fiancé by pretending to be an abominable cad. The film received good reviews, with Variety calling it "fresh, clever, excellently directed and produced, and acted by an ensemble that clicks from start to finish" and praising de Havilland.
Also released during 1937 was another period film with de Havilland, beginning with The Great Garrick, a fictional romantic comedy about the 18th-century English actor's encounter with jealous players from the Comédie-Française who plot to embarrass him on his way to Paris. Wise to their prank, Garrick plays along with the ruse, determined to get the last laugh, even on a lovely young aristocrat, de Havilland's Germaine Dupont, whom he mistakenly believes to be one of the players. With her refined demeanour and diction, de Havilland delivers a performance that is "lighthearted and thoroughly believable", according to Judith Kass. Variety praised the film, calling it "a production of superlative workmanship". Despite the positive reviews, the film did not do as well at the box office.
The Michael Curtiz-directed romantic drama Gold Is Where You Find It is a film about the late 19th-century conflict in the Sacramento Valley between gold miners and their hydraulic equipment and farmers whose land is being flooded. De Havilland played the daughter of a farmer, Serena Ferris, who falls in love with the mining engineer responsible for the flooding portrayed by George Brent. The picture also stars Claude Rains. The film was released in February 1938, and was her first appearance in a Technicolor film but not her last. She would make three more Technicolor films within the next two years, two of which would arguably remain her most fondly remembered by audiences across the decades since their release.
In September 1937, de Havilland was selected by Warner Bros. studio head Jack L. Warner to play Maid Marian opposite Errol Flynn in The Adventures of Robin Hood (1938). Principal photography for this Technicolor production took place between September 26, 1937, and January 14, 1938, including location work at Bidwell Park, Busch Gardens in Pasadena, and Lake Sherwood in California. Directed by William Keighley and Michael Curtiz, the film is about the legendary Saxon knight who opposes the corrupt and brutal Prince John and his Norman lords while good King Richard is away fighting in the Third Crusade. The king's ward Maid Marian initially opposes Robin Hood, but she later supports him after learning his true intentions of helping his oppressed people. No mere bystander to events, Marian risks her life to save Robin by providing his men with a plan for his escape. As defined by de Havilland, Marian is both a beautiful fairy-tale heroine and a spirited, intelligent woman "whose actions are governed by her mind as well as her heart", according to author Judith Kass. The Adventures of Robin Hood was released on May 14, 1938, and was an immediate critical and commercial success, earning an Academy Award nomination for Best Picture. It went on to become one of the most popular adventure films of the Classical Hollywood era.
The success of The Adventures of Robin Hood raised de Havilland's status, but this was not reflected in her subsequent film assignments at Warner Bros. Her next several roles were more routine and less challenging. In the romantic comedy Four's a Crowd (also 1938), she played Lorri Dillingwell, a flighty rich girl being romanced by a conniving public relations man looking to land an account with her eccentric grandfather. In Ray Enright's romantic comedy Hard to Get (1938), she played another frivolous rich girl, Margaret Richards, whose desire to exact revenge on a gas station attendant leads to her own comeuppance. In the summer of 1938, she portrayed the love interest between two U.S. Navy pilot brothers in Wings of the Navy, released in early 1939. While de Havilland was certainly capable of playing these kinds of characters, her personality was better suited to stronger and more dramatic roles, according to Judith Kass. By this time, de Havilland had serious doubts about her career at Warner Bros.
Some film scholars consider 1939 to be the high point of the golden age of Classic Cinema, producing award-winning, box office hits in many genres, including the Western. Warner Bros. produced Michael Curtiz's Technicolor adventure Dodge City (1939), Flynn and de Havilland's first Western film. Set during the American Civil War, the film is about a Texas trailblazer who witnesses the brutal lawlessness of Dodge City, Kansas, and becomes sheriff to clean up the town. De Havilland played Abbie Irving, whose initial hostility towards Flynn's character Wade Hatton is transformed by events, and the two fall in love—by now a proven formula for their on-screen relationships. Curtiz's action sequences, Sol Polito's cinematography, Max Steiner's expansive film score, and perhaps the "definitive saloon brawl in movie history" all contributed to the film's success. Variety described the film as "a lusty western, packed with action". For de Havilland, playing yet one more supporting love interest in a limited role, Dodge City represented the emotional low point of her career to that point. She later said, "I was in such a depressed state that I could hardly remember my lines."
In a letter to a colleague dated November 18, 1938, film producer David O. Selznick wrote, "I would give anything if we had Olivia de Havilland under contract to us so that we could cast her as Melanie." The film he was preparing to shoot was the Technicolor epic Gone with the Wind, and Jack L. Warner was unwilling to lend her out for the project. De Havilland had read the novel, and unlike most other actresses, who wanted the Scarlett O'Hara role, she wanted to play Melanie Hamilton—a character whose quiet dignity and inner strength she understood and felt she could bring to life on the screen.
De Havilland turned to Warner's wife Anne for help. Warner later recalled: "Olivia, who had a brain like a computer concealed behind those fawn-like eyes, simply went to my wife and they joined forces to change my mind." Warner relented, and de Havilland was signed to the project a few weeks before the start of principal photography on January 26, 1939. Set in the American South during the Civil War and Reconstruction eras, the film is about Scarlett O'Hara, the strong-willed daughter of a Georgia plantation owner in love with the husband of her sister-in-law Melanie, whose kindness stands in sharp contrast to those around her. According to film historian Tony Thomas, de Havilland's skillful and subtle performance effectively presents this character of selfless love and quiet strength in a way that keeps her vital and interesting throughout the film. Gone with the Wind had its world premiere in Atlanta, Georgia, on December 15, 1939, and was well received. Frank S. Nugent of The New York Times wrote that de Havilland's Melanie "is a gracious, dignified, tender gem of characterization", and John C. Flinn Sr. in Variety called her "a standout". The film won 10 Academy Awards, including Best Picture, and de Havilland received her first nomination for Best Supporting Actress.
Within days of completing her work in Gone with the Wind in June 1939, de Havilland returned to Warner Bros. and began filming Michael Curtiz's historical drama The Private Lives of Elizabeth and Essex (also 1939) with Bette Davis and Errol Flynn. She had hoped her work on Selznick's prestige picture would lead to first-rate roles at Warner Bros., but instead, she received third billing below the title as the queen's lady-in-waiting. In early September, she was lent out to Samuel Goldwyn Productions for Sam Wood's romantic caper film Raffles (also 1939) with David Niven, about a high-society cricketer and jewel thief. She later complained, "I had nothing to do with that style of film."
In early 1940, de Havilland refused to appear in several films assigned to her, initiating the first of her suspensions at the studio. She did agree to play in Curtis Bernhardt's musical comedy drama My Love Came Back (1940) with Jeffrey Lynn and Eddie Albert, who played a classical music student turned swing jazz bandleader. De Havilland played violinist Amelia Cornell, whose life becomes complicated by the support of a wealthy sponsor. In his review in The New York Times, Bosley Crowther described the film as "a featherlight frolic, a rollicking roundelay of deliciously pointed nonsense", finding that de Havilland "plays the part with pace and wit".
That same year, de Havilland was re-united with Flynn in their sixth film together, Michael Curtiz's Western adventure Santa Fe Trail, set against the backdrop of abolitionist John Brown's fanatical anti-slavery attacks in the days leading up to the American Civil War. The mostly fictional story follows West Point cadets J. E. B. Stuart, played by Flynn, and George Armstrong Custer, played by Ronald Reagan, as they make their way west, both vying for the affection of de Havilland's Kit Carson Halliday. Playing Kit in a provocative, tongue-in-cheek manner, de Havilland creates a character of real substance and dimension, according to Tony Thomas. Following a world premiere on December 13, 1940, at the Lensic Theatre in Santa Fe, New Mexico—attended by cast members, reporters, the governor, and over 60,000 fans — Santa Fe Trail became one of the top-grossing films of 1940. De Havilland, who accompanied Flynn on the well-publicised train ride to Santa Fe, did not attend the premiere, having been diagnosed with appendicitis that morning and rushed into surgery.
Following her emergency surgery, de Havilland began a long period of convalescence in a Los Angeles hospital during which time she rejected several scripts offered to her by Warner Bros., leading to another suspension. She appeared in three commercially successful films released in 1941, beginning with Raoul Walsh's romantic comedy The Strawberry Blonde with James Cagney. Set during the Gay Nineties, the story involves a man who marries an outspoken advocate for women's rights after a rival steals his glamorous "strawberry blonde" girlfriend, and later discovers he ended up with a loving and understanding wife. The film was a critical and commercial success. In Mitch Leisen's romantic drama Hold Back the Dawn with Charles Boyer for Paramount Pictures, she transitioned to a different type of role for her—an ordinary, decent small-town teacher whose life and sexuality are awakened by a sophisticated European gigolo, whose own life is positively affected by her love. Leisen's careful direction and guidance appealed to de Havilland—much more than the workman-like approach of her Warner Bros. directors. Bosley Crowther of The New York Times wrote that the actress "plays the school teacher as a woman with romantic fancies whose honesty and pride are her own—and the film's—chief support. Incidentally, she is excellent." For this performance, she garnered her second Academy Award nomination—this time for Best Actress.
De Havilland was re-united with Flynn for their eighth movie together, Raoul Walsh's epic They Died with Their Boots On. The film is loosely based on the courtship and marriage of George Armstrong Custer and Elizabeth "Libbie" Bacon. Flynn and de Havilland had a falling out the previous year—mainly over the roles she was being given—and she did not intend to work with him again. Even Flynn acknowledged, "She was sick to death of playing 'the girl' and badly wanted a few good roles to show herself and the world that she was a fine actress." After she learned from Warner that Flynn had come to his office saying he needed her in the film, de Havilland accepted. Screenwriter Lenore Coffee was brought in to add several romantic scenes and improve the overall dialogue. The result is a film that includes some of their finest work together. Their last appearance on screen is Custer's farewell to his wife. "Errol was quite sensitive", de Havilland would later remember, "I think he knew it would be the last time we worked together." Flynn's final line in that scene would hold special meaning for her: "Walking through life with you, ma'am, has been a very gracious thing." They Died with Their Boots On was released on November 21, 1941, and while some reviewers criticised the film's historical inaccuracies, most applauded the action sequences, cinematography, and acting. Thomas M. Pryor of The New York Times found de Havilland "altogether captivating". The film went on to earn $2,550,000 (equivalent to $47,000,000 in 2021), Warner Bros' second-biggest money-maker of that year.
De Havilland appeared in Elliott Nugent's romantic comedy The Male Animal (1942) with Henry Fonda, about an idealistic professor fighting for academic freedom while trying to hold onto his job and his wife Ellen, portrayed by de Havilland. While her role was not particularly challenging, de Havilland's delineation of an intelligent, good-natured woman trying to resolve the unsettling circumstances of her life played a major part in the film's success, according to Tony Thomas. The film was a critical and commercial success, with Bosley Crowther of The New York Times noting that de Havilland "concocts a delightfully pliant and saucy character as the wife".
Around the same time, she appeared in John Huston's drama In This Our Life (also 1942) with Bette Davis. Based on the Pulitzer Prize-winning novel of the same name by Ellen Glasgow, the story is about two sisters whose lives are destroyed by the anger and jealousy of one of the sisters. Crowther gave the film a negative review, but praised de Havilland's "warm and easy performance". During production, de Havilland and Huston began a romantic relationship that lasted three years.
According to de Havilland, one of the few truly satisfying roles she played for Warner Bros. was the title character in Norman Krasna's romantic comedy Princess O'Rourke (1943), with Robert Cummings. Filmed in July and August 1942, the story is about a European princess in New York City visiting her diplomat uncle, who is trying to find her an American husband. Intent on marrying a man of her own choosing, she boards a plane heading west and ends up falling in love with an American pilot, who is unaware of her true identity. The film was released on October 23, 1943, and did well at the box office. Bosley Crowther called it "a film which is in the best tradition of American screen comedy", and found de Havilland's performance "charming".
After fulfilling her seven-year Warner Bros. contract in 1943, de Havilland was informed that six months had been added to her contract for the times that she had been suspended. At the time, the studios had adopted the position that California law allowed them to suspend contract players for rejecting a role, and the period of suspension could be added to the contract period. Most contract players accepted this, but a few tried to challenge this assumption, including Bette Davis, who mounted an unsuccessful lawsuit against Warner Bros. in the 1930s. On August 23, 1943, acting on the advice of her lawyer Martin Gang, de Havilland filed suit against Warner Bros. in Los Angeles County Superior Court seeking declaratory judgment that she was no longer bound by her contract on the grounds that an existing section of the California Labor Code forbade an employer from enforcing a contract against an employee for longer than seven years from the date of first performance. In November 1943, the court found in de Havilland's favour, and Warner Bros. immediately appealed. A little over a year later, the California Court of Appeal for the Second District ruled in her favour. The decision was one of the most significant and far-reaching legal rulings in Hollywood, reducing the power of the studios and extending greater creative freedom to performers. California's resulting "seven-year rule", as articulated by the Court of Appeal in analysing Labor Code Section 2855 in the De Havilland case, is still known as the De Havilland Law. Her legal victory, which cost her $13,000 (equivalent to $200,000 in 2021) in legal fees, won de Havilland the respect and admiration of her peers, among them her own sister Joan Fontaine, who later commented, "Hollywood owes Olivia a great deal." Warner Bros. reacted to de Havilland's lawsuit by circulating a letter to other studios that had the effect of a "virtual blacklisting." As a consequence, de Havilland did not work at a film studio for nearly two years.
De Havilland became a naturalized citizen of the United States on November 28, 1941, 10 days before the United States entered World War II militarily. During the war years, she actively contributed to the war effort. In May 1942, she joined the Hollywood Victory Caravan, a three-week train tour of the country that raised money through the sale of war bonds. Later that year, she began attending events at the Hollywood Canteen, meeting and dancing with troops. In December 1943, de Havilland joined a USO tour that travelled throughout the United States and the South Pacific, visiting wounded soldiers in military hospitals. She earned the respect and admiration of the troops for visiting the isolated islands and battlefronts in the Pacific. She survived flights in damaged aircraft and a bout with viral pneumonia requiring several days' stay in one of the island barrack hospitals. She later remembered, "I loved doing the tours because it was a way I could serve my country and contribute to the war effort."
After the California Court of Appeal ruling freed her from her Warner Bros. contract, de Havilland signed a two-picture deal with Paramount Pictures. In June 1945, she began filming Mitchell Leisen's drama To Each His Own, (1946) about an unwed mother who gives up her child for adoption and then spends the rest of her life trying to undo that decision. De Havilland insisted on bringing in Leisen as director, trusting his eye for detail, his empathy for actors, and the way he controlled sentiment in their previous collaboration, Hold Back the Dawn. The role required de Havilland to age nearly 30 years over the course of the film—from an innocent, small-town girl to a shrewd, ruthless businesswoman devoted to her cosmetics company. While de Havilland never formally studied acting, she did read Stanislavsky's autobiography My Life in Art and applied one of his "methods" for this role. To help her define her character during the four periods of the story, she used a different perfume for each period. She also lowered the pitch of her voice incrementally in each period until it became a mature woman's voice. Her performance earned her the Academy Award for Best Actress for 1946—her first Oscar. According to film historian Tony Thomas, the award represented a vindication of her long struggle with Warner Bros. and confirmation of her abilities as an actress.
Her next two roles were challenging. In Robert Siodmak's psychological thriller The Dark Mirror (also 1946), de Havilland played twin sisters Ruth and Terry Collins—one loving and normal, the other psychotic. In addition to the technical problems of showing her as two characters interacting with each other on screen at the same time, de Havilland needed to portray two separate and psychologically opposite people. While the film was not well received by critics—Variety said the film "gets lost in a maze of psychological gadgets and speculation"—de Havilland's performance was praised by Tony Thomas, who called her final scene in the film "an almost frighteningly convincing piece of acting". In his review in The Nation, James Agee wrote that "her playing is thoughtful, quiet, detailed, and well sustained, and since it is founded, as some more talented playing is not, in an unusually healthful-seeming and likable temperament, it is an undivided pleasure to see". Later that year while appearing in a summer stock production of What Every Woman Knows in Westport, Connecticut, her second professional stage appearance, de Havilland began dating Marcus Goodrich, a U.S. Navy veteran, journalist, and author of the novel Delilah (1941). The couple married on August 26, 1946.
De Havilland was praised for her performance as Virginia Cunningham in Anatole Litvak's drama The Snake Pit (1948), one of the first films to attempt a realistic portrayal of mental illness and an important exposé of the harsh conditions in state mental hospitals, according to film critic Philip French. Based on a novel by Mary Jane Ward and produced by Darryl F. Zanuck, the film is about a woman placed in a mental institution by her husband to help her recover from a nervous breakdown. Virginia Cunningham was one of the most difficult of all her film roles, requiring significant preparation both mentally and physically—she deliberately lost weight to help create her gaunt appearance on screen. She consulted regularly with psychiatrists hired as consultants for the film, and visited Camarillo State Mental Hospital to research her role and observe the patients. The extreme physical discomfort of the hydrotherapy and simulated electric shock therapy scenes were especially challenging for the slight 5-foot-3-inch (160 cm) actress. In her performance, she conveyed her mental anguish by physically transforming her face with furrowed brow, wild staring eyes, and grimacing mouth.
According to author Judith Kass, de Havilland delivered a performance both "restrained and electric", portraying varied and extreme aspects of her character—from a shy young woman to a tormented and disorientated woman. For her performance in The Snake Pit, de Havilland received an Academy Award nomination for Best Actress, the New York Film Critics Circle Award for Best Actress, and the Venice Film Festival Volpi Cup.
De Havilland appeared in William Wyler's period drama The Heiress (1949), the fourth in a string of critically acclaimed performances. After seeing the play on Broadway, de Havilland called Wyler and urged him to fly to New York to see what she felt would be a perfect role for her. Wyler obliged, loved the play, and with de Havilland's help arranged for Paramount to secure the film rights. Adapted for the screen by Ruth and Augustus Goetz and based on the 1880 novel Washington Square by Henry James, the film is about a young naïve woman who falls in love with a young man (Montgomery Clift), over the objections of her cruel and emotionally abusive father, who suspects the young man of being a fortune seeker. As she had done in Hold Back the Dawn, de Havilland portrayed her character's transformation from a shy, trusting innocent to a guarded, mature woman over a period of years. Her delineation of Catherine Sloper is developed through carefully crafted movements, gestures, and facial expressions that convey a submissive and inhibited young woman. Her timid voice, nervous hands, downcast eyes, and careful movements all communicate what the character is too shy to verbalise. Throughout the production, Wyler pressed de Havilland hard to elicit the requisite visual points of the character. When Catherine returns home after being jilted, the director had the actress carry a suitcase filled with heavy books up the stairs to convey the weight of Catherine's trauma physically instead of using a planned speech in the original script. The Heiress was released in October 1949 and was well received by critics. For her performance, she received the New York Film Critics Award, the Golden Globe Award, and the Academy Award for Best Actress—her second Oscar.
After giving birth to her first child, Benjamin, on September 27, 1949, de Havilland took time off from making films to be with her infant son. She turned down the role of Blanche DuBois in A Streetcar Named Desire, later explaining that becoming a mother was a "transforming experience" and that she could not relate to the character. In 1950, her family moved to New York City, where she began rehearsals for a major new stage production of Shakespeare's Romeo and Juliet; it was her life-long ambition to play Juliet on the stage. The play opened at the Broadhurst Theatre on March 11, 1951, to mixed reviews, with some critics believing the 35-year-old actress was too old for the role. The play closed after 45 performances. Undaunted, de Havilland accepted the title role in the stage production of George Bernard Shaw's comedy Candida, which opened at the National Theatre on Broadway in April 1952. While reviews of the play were mixed, de Havilland's performance was well received, and following the scheduled 32 performances, she went on tour with the company and delivered 323 additional performances, many to sold-out audiences. While de Havilland achieved major accomplishments during this period of her career, her marriage to Goodrich, 18 years her senior, had grown strained because of his unstable temperament. In August 1952, she filed for divorce, which became final the following year.
In April 1953, at the invitation of the French government, she travelled to the Cannes Film Festival, where she met Pierre Galante, an executive editor for the French journal Paris Match. Following a long-distance courtship and the requisite nine-month residency requirement, de Havilland and Galante married on April 12, 1955, in the village of Yvoy-le-Marron, and settled together in a three-storey house near the Bois de Boulogne park in Paris' 16th Arrondissement. That same year, she returned to the screen in Terence Young's period drama That Lady (1955), about a Spanish princess and her unrequited love for King Philip II of Spain, whose respect she earned in her youth after losing an eye in a sword fight defending his honor. According to Tony Thomas, the film uses authentic Spanish locations effectively, but suffers from a convoluted plot and excessive dialogue, and while de Havilland delivered a warm and elegant performance as Ana de Mendoza, the film was disappointing. Following her appearances in the romantic melodrama Not as a Stranger (1955) and The Ambassador's Daughter (1956)—neither of which were successful at the box office—de Havilland gave birth to her second child, Gisèle Galante, on July 18, 1956.
De Havilland returned to the screen in Michael Curtiz's Western drama The Proud Rebel (1958), a film about a former Confederate soldier (Alan Ladd) whose wife was killed in the war and whose son lost the ability to speak after witnessing the tragedy. De Havilland played Linnett Moore, a tough yet feminine frontier woman who cares for the boy and comes to love his father. The movie was filmed on location in Utah, where de Havilland learned to hitch and drive a team of horses and handle a gun for her role. The Proud Rebel was released May 28, 1958, and was well received by audiences and critics. In his review for The New York Times, A. H. Weiler called the film a "truly sensitive effort" and "heartwarming drama", and praised de Havilland's ability to convey the "warmth, affection and sturdiness needed in the role".
One of de Havilland's best received performances during this period was in Guy Green's romantic drama Light in the Piazza (1962) with Rossano Brazzi. Filmed in Florence and Rome, and based on Elizabeth Spencer's novel of the same name, the film is about a middle-class American tourist on extended vacation in Italy with her beautiful 26-year-old daughter (Yvette Mimieux), who is mentally disabled as a result of a childhood accident. Faced with the prospect of her daughter falling in love with a young Italian, the mother struggles with conflicting emotions about her daughter's future. De Havilland projects a calm maternal serenity throughout most of the film, only showing glimpses of the worried mother anxious for her child's happiness. The film was released on February 19, 1962, and was well received, with a Hollywood Reporter reviewer calling it "an uncommon love story ... told with rare delicacy and force", and Variety noting that the film "achieves the rare and delicate balance of artistic beauty, romantic substance, dramatic novelty and commercial appeal". Variety singled out de Havilland's performance as "one of great consistency and subtle projection".
In early 1962, de Havilland traveled to New York City, and began rehearsals for Garson Kanin's stage play A Gift of Time. Adapted from the autobiographical book Death of a Man by Lael Tucker Wertenbaker, the play explores the emotionally painful struggle of a housewife forced to deal with the slow death of her husband, played by Henry Fonda. The play opened at the Ethel Barrymore Theatre on Broadway to positive notices, with de Havilland receiving her best reviews as a stage actress. Theatre critic Walter Kerr praised her final scene, writing, "As darkness gathers, the actress gains in stature, taking on the simple and resolute willingness to understand." The New York World Telegram and Sun reviewer concluded: "It is Miss de Havilland who gives the play its unbroken continuity. This distinguished actress reveals Lael as a special and admirable woman." She stayed with the production for 90 performances. The year 1962 also saw the publication of de Havilland's first book, Every Frenchman Has One, a lighthearted account of her often amusing attempts to understand and adapt to French life, manners, and customs. The book sold out its first printing prior to the publication date and went on to become a bestseller.
De Havilland appeared in her final motion picture leading roles in two films released in 1964, both of which were psychological thrillers. In Walter Grauman's Lady in a Cage, she played a wealthy poet who becomes trapped in her mansion's elevator and faces the threat of three terrorising hooligans in her own home. Critics responded negatively to the graphic violence and cruelty shown on screen. A. H. Weiler of The New York Times called it a "sordid, if suspenseful, exercise in aimless brutality". That same year, de Havilland appeared in Robert Aldrich's Hush...Hush, Sweet Charlotte with her close friend Bette Davis. After Joan Crawford left the picture owing to illness, Davis had Aldrich fly to Switzerland to persuade a reluctant de Havilland to accept the role of Miriam Deering, a cruel, conniving character hidden behind the charming façade of a polite and cultured lady. Her quiet, restrained performance provided a counterbalance to Davis. Film historian Tony Thomas described her performance as "a subtle piece of acting" that was "a vital contribution to the effectiveness of the film". The film was mainly well received and earned seven Academy Award nominations. In 1965 she served as the President of the Jury of the 18th Cannes Film Festival, the first woman to do so.
As film roles became more difficult to find, a common problem shared by many Hollywood veterans from her era, de Havilland began working in television dramas, despite her dislike of the networks' practice of breaking up story lines with commercials. Her first venture into the medium was a teleplay directed by Sam Peckinpah called Noon Wine (1966) on ABC Stage 67, a dark tragedy about a farmer's act of murder that leads to his suicide. The production and her performance as the farmer's wife Ellie were well received. In 1972, she starred in her first television film, The Screaming Woman, about a wealthy woman recovering from a nervous breakdown. In 1979, she appeared in the ABC miniseries Roots: The Next Generations in the role of Mrs. Warner, the wife of a former Confederate officer played by Henry Fonda. The miniseries was seen by an estimated 110 million people—nearly one-third of American homes with television sets. Throughout the 1970s, de Havilland's film work was limited to smaller supporting roles and cameo appearances. Her last feature film was The Fifth Musketeer (1979). During this period, de Havilland began doing speaking engagements in cities across the United States with a talk entitled "From the City of the Stars to the City of Light", a programme of personal reminiscences about her life and career. She also attended tributes to Gone with the Wind.
In the 1980s, her television work included an Agatha Christie television film Murder Is Easy (1982), the television drama The Royal Romance of Charles and Diana (1982) in which she played the Queen Mother, and the 1986 ABC miniseries North and South, Book II. Her performance in the television film Anastasia: The Mystery of Anna (1986), as Dowager Empress Maria, earned her a Golden Globe Award for Best Supporting Actress in a Series, Miniseries or Television Film. In 1988, de Havilland appeared in the HTV romantic television drama The Woman He Loved; it was her final screen performance.
In retirement, de Havilland remained active in the film community. In 1998, she travelled to New York City to help promote a special showing of Gone with the Wind. In 2003, she appeared as a presenter at the 75th Academy Awards, earning an extended standing ovation upon her entrance. In 2004, Turner Classic Movies produced a retrospective piece called Melanie Remembers in which she was interviewed for the 65th anniversary of the original release of Gone with the Wind. In June 2006, she made appearances at tributes commemorating her 90th birthday at the Academy of Motion Picture Arts and Sciences and the Los Angeles County Museum of Art.
On November 17, 2008, at the age of 92, de Havilland received the National Medal of Arts, the highest honor conferred to an individual artist on behalf of the people of the United States. The medal was presented to her by President George W. Bush, who commended her "for her persuasive and compelling skill as an actress in roles from Shakespeare's Hermia to Margaret Mitchell's Melanie. Her independence, integrity, and grace won creative freedom for herself and her fellow film actors." The following year, de Havilland narrated the documentary I Remember Better When I Paint (2009), a film about the importance of art in the treatment of Alzheimer's disease.
In 2010, de Havilland almost made her return to the big screen after a 22-year hiatus with James Ivory's planned adaptation of The Aspern Papers, but the project was never made. On September 9, 2010, de Havilland was appointed a Chevalier (knight) of the Légion d'honneur, the highest decoration in France, awarded by President Nicolas Sarkozy, who told the actress, "You honor France for having chosen us." In February the following year, she appeared at the César Awards in France, where she was greeted with a standing ovation. De Havilland celebrated her 100th birthday on July 1, 2016.
In June 2017, two weeks before her 101st birthday, de Havilland was appointed Dame Commander of the Order of the British Empire in the 2017 Birthday Honours for services to drama by Queen Elizabeth II. She is the oldest woman ever to receive the honor. In a statement, she called it "the most gratifying of birthday presents". She did not travel to the investiture ceremony at Buckingham Palace and received her honor from the hands of the British Ambassador to France at her Paris apartment in March 2018, four months before her 102nd birthday. Her daughter Gisèle was by her side.