Early Career and War Service
Guinness first worked writing advertising copy. His first job in the theatre was on his 20th birthday, while he was still a drama student, in the play Libel, which opened at the old King's Theatre, Hammersmith, and then transferred to the Playhouse where his status was raised from a walk-on to understudying two lines and his salary increased to £1 a week. He appeared at the Albery Theatre in 1936 at the age of 22, playing the role of Osric in John Gielgud's successful production of Hamlet. 1936 also saw Guinness sign on with the Old Vic, where he was cast in a series of classic roles. During this time he worked with many actors and actresses who would become his friends and frequent co-stars in the future, including John Gielgud, Peggy Ashcroft, Anthony Quayle and Jack Hawkins. An early influence from afar was Stan Laurel, whom Guinness admired.
Guinness continued playing Shakespearean roles throughout his career. In 1937 he played Aumerle in Richard II and Lorenzo in The Merchant of Venice under the direction of John Gielgud. He starred in a 1938 production of Hamlet which won him acclaim on both sides of the Atlantic. He also appeared as Romeo in a production of Romeo and Juliet (1939), Andrew Aguecheek in Twelfth Night and as Exeter in Henry V in 1937, both opposite Laurence Olivier, and Ferdinand in The Tempest, opposite Gielgud as Prospero.
In 1939, he adapted Charles Dickens' novel Great Expectations for the stage, playing the part of Herbert Pocket. The play was a success. One of its viewers was a young British film editor, David Lean, who would later have Guinness reprise his role in Lean's 1946 film adaptation of the play.
Guinness served in the Royal Navy Volunteer Reserve in World War II, serving first as a seaman in 1941 and being commissioned the following year. He commanded a landing craft taking part in the invasion of Sicily and Elba and later ferried supplies to the Yugoslav partisans.
During the war, he was granted leave to appear in the Broadway production of Terence Rattigan's play Flare Path, about the RAF Bomber Command.
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—Henry David Thoreau (1817–1862)