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1954–1961: Early work and rise to prominence

O'Toole began working in the theatre, gaining recognition as a Shakespearean actor at the Bristol Old Vic and with the English Stage Company, before making his television debut in 1954. He played a soldier in an episode of The Scarlet Pimpernel in 1954. He was based at the Bristol Old Vic from 1956 to 1958, appearing in productions of King Lear, The Recruiting Officer, Major Barbara, Othello, and The Slave of Truth (all 1956). He was Henry Higgins in Pygmalion, Lysander in A Midsummer Night's Dream, Uncle Gustave in Oh! My Papa!, and Jimmy Porter in Look Back in Anger (all 1957). O'Toole was Tanner in Shaw's Man and Superman (1958), a performance he reprised often during his career. He was also in Hamlet, The Holiday, Amphitryon '38, and Waiting for Godot (as Vladimir; all 1958). He hoped The Holiday would take him to the West End but it ultimately folded in the provinces; during that show he met Siân Phillips who became his first wife.

O'Toole continued to appear on television, being in episodes of Armchair Theatre ("The Pier", 1957), and BBC Sunday-Night Theatre ("The Laughing Woman", 1958) and was in the TV adaptation of The Castiglioni Brothers (1958). He made his London debut in a musical, Oh, My Papa. He gained fame on the West End in the play The Long and the Short and the Tall, performed at the Royal Court beginning in January 1959. His co-stars included Robert Shaw and Edward Judd, and it was directed by Lindsay Anderson. O'Toole reprised his performance for television on Theatre Night in 1959 (although he did not appear in the 1961 film version). The show transferred to the West End in April and won O'Toole Best Actor of the Year in 1959.

O'Toole was in much demand. He reportedly received five offers of long-term contracts but turned them down. His first role was a small role in Disney's version of Kidnapped (1960), playing the bagpipes opposite Peter Finch. His second feature was The Savage Innocents (1960) with Anthony Quinn for director Nicholas Ray. With his then wife Sian Phillips he did Siwan: The King's Daughter (1960) for TV. In 1960 he had a nine-month season at the Royal Shakespeare Company in Stratford, appearing in The Taming of the Shrew (as Petruchio), The Merchant of Venice (as Shylock) and Troilus and Cressida (as Thersites). He could have made more money in films but said "You've got to go to Stratford when you've got the chance."

O'Toole had been seen in The Long and the Short and the Tall by Jules Buck who later established a company with the actor. Buck cast O'Toole in The Day They Robbed the Bank of England (1961), a heist thriller from director John Guillermin. O'Toole was billed third, beneath Aldo Ray and Elizabeth Sellars. The same year he appeared in several episodes of the TV series Rendezvous ("End of a Good Man", "Once a Horseplayer", "London-New York"). He lost the role in the film adaptation of Long and the Short and the Tall to Laurence Harvey. "It broke my heart", he said later.