With her mind still set on becoming a teacher, de Havilland initially wavered, but eventually, Reinhardt and executive producer Henry Blanke persuaded her to sign a five-year contract with Warner Bros. on November 12, 1934, with a starting salary of $200 a week, marking the beginning of a professional acting career which would span more than 50 years.

[41] Filmed between August 5 and October 29, 1935,[42] 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.

[49] The popular success of the film, as well as the critical response to the on-screen couple, led to seven additional collaborations:[43] 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).

[50] 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.

[66] 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.

[67] 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.

[68] 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.

[69] 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.

[81] 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.

[65] 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.

[89] 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.

[92] By this time, de Havilland had serious doubts about her career at Warner Bros.[93][94] Some film scholars consider 1939 to be the high point of the golden age of Classic Cinema,[95] producing award-winning, box office hits in many genres, including the Western.

[106] 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.

[13]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.

[113] In early September, she was lent out to Samuel Goldwyn Productions for Sam Wood's romantic caper film Raffles (also 1939) with David Niven,[114] about a high-society cricketer and jewel thief.

[116][Note 8] 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".

[118] 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 radical anti-slavery attacks in the days leading up to the American Civil War.

[124] 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.

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.

[172] 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.

[195] 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.

[201][202][203] 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.

[203] De Havilland returned to the screen in Michael Curtiz's Western drama The Proud Rebel (1958),[207] 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.

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".

[219] 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.

[223] 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.

[196] After the war, she joined The Independent Citizens Committee of the Arts, Sciences and Professions, a national public-policy advocacy group that included Bette Davis, Gregory Peck, Groucho Marx, and Humphrey Bogart in its Hollywood chapter.

[263] Disturbed at seeing a small group of communist members manipulating the committee, she removed the pro-communist material from her speeches and rewrote them to reflect Democratic president Harry S. Truman's anti-communist platform.

[272][273] The final break between the sisters occurred in 1975 over disagreements regarding their mother's cancer treatment; de Havilland wanted to consult other doctors and supported exploratory surgery but Fontaine disagreed.

[286] The moving-image collection of Olivia de Havilland is held at the Academy Film Archive, which preserved a nitrate reel of a screen test for Danton, Max Reinhardt's never-produced follow-up to A Midsummer Night's Dream (1935).