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1957–1963: Royal Court and Chichester

During the production of The Prince and the Showgirl, Olivier, Monroe and her husband, the American playwright Arthur Miller, went to see the English Stage Company's production of John Osborne 's Look Back in Anger at the Royal Court. Olivier had seen the play earlier in the run and disliked it, but Miller was convinced that Osborne had talent, and Olivier reconsidered. He was ready for a change of direction; in 1981 he wrote:

I had reached a stage in my life that I was getting profoundly sick of—not just tired—sick. Consequently the public were, likely enough, beginning to agree with me. My rhythm of work had become a bit deadly: a classical or semi-classical film; a play or two at Stratford, or a nine-month run in the West End, etc etc. I was going mad, desperately searching for something suddenly fresh and thrillingly exciting. What I felt to be my image was boring me to death.

Osborne was already at work on a new play, The Entertainer, an allegory of Britain's post-colonial decline, centred on a seedy variety comedian, Archie Rice. Having read the first act—all that was completed by then—Olivier asked to be cast in the part. He had for years maintained that he might easily have been a third-rate comedian called "Larry Oliver", and would sometimes play the character at parties. Behind Archie's brazen façade there is a deep desolation, and Olivier caught both aspects, switching, in the words of the biographer Anthony Holden, "from a gleefully tacky comic routine to moments of the most wrenching pathos". Tony Richardson 's production for the English Stage Company transferred from the Royal Court to the Palace Theatre in September 1957; after that it toured and returned to the Palace. The role of Archie's daughter Jean was taken by three actresses during the various runs. The second of them was Joan Plowright, with whom Olivier began a relationship that endured for the rest of his life. Olivier said that playing Archie "made me feel like a modern actor again". In finding an avant-garde play that suited him, he was, as Osborne remarked, far ahead of Gielgud and Ralph Richardson, who did not successfully follow his lead for more than a decade. Their first substantial successes in works by any of Osborne's generation were Alan Bennett 's Forty Years On (Gielgud in 1968) and David Storey 's Home (Richardson and Gielgud in 1970).

Olivier received another BAFTA nomination for his supporting role in 1959's The Devil's Disciple. The same year, after a gap of two decades, Olivier returned to the role of Coriolanus, in a Stratford production directed by the 28-year-old Peter Hall. Olivier's performance received strong praise from the critics for its fierce athleticism combined with an emotional vulnerability. In 1960 he made his second appearance for the Royal Court company in Ionesco 's absurdist play Rhinoceros. The production was chiefly remarkable for the star's quarrels with the director, Orson Welles, who according to the biographer Francis Beckett suffered the "appalling treatment" that Olivier had inflicted on Gielgud at Stratford five years earlier. Olivier again ignored his director and undermined his authority. In 1960 and 1961 Olivier appeared in Anouilh's Becket on Broadway, first in the title role, with Anthony Quinn as the king, and later exchanging roles with his co-star.

Two films featuring Olivier were released in 1960. The first—filmed in 1959—was Spartacus, in which he portrayed the Roman general, Marcus Licinius Crassus. His second was The Entertainer, shot while he was appearing in Coriolanus; the film was well received by the critics, but not as warmly as the stage show had been. The reviewer for The Guardian thought the performances were good, and wrote that Olivier "on the screen as on the stage, achieves the tour de force of bringing Archie Rice... to life". For his performance, Olivier was nominated for the Academy Award for Best Actor. He also made an adaptation of The Moon and Sixpence in 1960, winning an Emmy Award.

The Oliviers' marriage was disintegrating during the late 1950s. While directing Charlton Heston in the 1960 play The Tumbler, Olivier divulged that "Vivien is several thousand miles away, trembling on the edge of a cliff, even when she's sitting quietly in her own drawing room", at a time when she was threatening suicide. In May 1960 divorce proceedings started; Leigh reported the fact to the press and informed reporters of Olivier's relationship with Plowright. The decree nisi was issued in December 1960, which enabled him to marry Plowright in March 1961. A son, Richard, was born in December 1961; two daughters followed, Tamsin Agnes Margaret—born in January 1963—and actress Julie-Kate, born in July 1966.

In 1961 Olivier accepted the directorship of a new theatrical venture, the Chichester Festival. For the opening season in 1962 he directed two neglected 17th-century English plays, John Fletcher 's 1638 comedy The Chances and John Ford 's 1633 tragedy The Broken Heart, followed by Uncle Vanya. The company he recruited was forty strong and included Thorndike, Casson, Redgrave, Athene Seyler, John Neville and Plowright. The first two plays were politely received; the Chekhov production attracted rapturous notices. The Times commented, "It is doubtful if the Moscow Arts Theatre itself could improve on this production." The second Chichester season the following year consisted of a revival of Uncle Vanya and two new productions—Shaw's Saint Joan and John Arden 's The Workhouse Donkey. In 1963 Olivier received another BAFTA nomination for his leading role as a schoolteacher accused of sexually molesting a student in the film Term of Trial.