At 21, Milland went to London and joined the British Household Cavalry. He trained for several months, learning fencing, boxing and shooting, and won the Bisley Match for his team. In 1928, he decided to become an actor.
He initially appeared as an extra in ‘Piccadilly’ (1929) and other insignificant roles. Later he got hired as an extra at the British International Pictures studio, in Arthur Robison's production of ‘The Informer’ (1929).
After a while, Director Castleton Knight cast him in his first major role in ‘The Flying Scotsman’ (1929). Around this time, he adopted the screen name ‘Milland’. His performance in the film won him a six-month contract and he starred in two more films directed by Knight, ‘The Lady from the Sea’ and ‘The Plaything’.
Eager to improve his acting skills, he decided to do some stage work and enacted the second lead in a production of Shipman and Marcin's ‘The Woman in Room 13’. Within five weeks he acquired valuable acting experience.
Meanwhile, MGM vice-president Robert Rubin approached him and offered him a nine-month contract, based in Hollywood. He accepted the offer and left the United Kingdom in August 1930.
In the beginning, MGM cast him as a character actor, featuring him in mainstream productions but in less speaking roles. In this initial phase, he faced a lot of criticism for acting.
Unabashed, he continued in Hollywood and in 1930 appeared in his first US film ‘Passion Flower’. Over the next two years, he appeared in several minor roles for MGM and a few uncredited roles in films loaned out to Warner Brothers. His most prominent role during this period was in ‘Payment Deferred’ (1932).
Shortly afterwards, MGM refused to renew his contract and he was out of work. Hence, he returned to England, hoping to land roles in British films based on his Hollywood experience.
In Britain, he appeared in two unimportant films, ‘This is the Life’ and ‘Orders is Orders’ (1934), but failed to find regular work. He eventually returned to the US and took to menial jobs. After a while, he received an offer to act in Paramount Pictures - George Raft’s film ‘Bolero’ (1934).
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Next, he appeared in a screwball musical comedy, ‘We're Not Dressing’ (1934). His stellar performance won the confidence of director Norman Taurog and he was signed for seven years with Paramount Pictures.
Initially, Paramount cast him in less speaking roles. In 1936, Joe Pasternak from Universal Studios approached him for playing the lead role in ‘Three Smart Girls’; Paramount agreed to loan him out.
Later that year, he appeared in the huge hit ‘The Jungle Princess’ opposite starlet Dorothy Lamour. By the end of 1936, he was being considered for lead roles. Paramount rewrote his contract, tripling his salary.
In 1937, he was cast in ‘Bulldog Drummond Escapes’. This was followed by another lead role in ‘Gilded Lily’. Eventually, he acted in ‘Ebb Tide’ for Paramount and a couple of loan-out films for Universal and Columbia Pictures.
In 1939, while shooting for ‘Hotel Imperial’, he suffered a near-fatal injury. The accident badly damaged his left hand. Soon after, a second injury followed in which he lost his left thumb.
Notwithstanding the pain, he flew to England to star in ‘French Without Tears’. By the time he returned to the US, World War II had been declared in Europe. In 1939 he appeared in ‘Beau Geste’ and ‘Everything Happens at Night’.
In 1940, he acted with some of the leading ladies of the era such as ‘Arise, My Love’ with Claudette Colbert, ‘Irene’ opposite Anna Neagle, and ‘Untamed’ with Patricia Morison.
He was eager to enlist in the US Air Force during the war, but was turned down because of his damaged left hand. Nevertheless, he worked as a civilian flight instructor for the army.
As the war continued, he acted in more action orientated films like ‘I Wanted Wings’ (1941) and ‘Reap the Wild Wind’ (1942). In 1943, he appeared in the all-star musical ‘Star Spangled Rhythm’ and the collaborative drama ‘Forever and a Day’.
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In 1944, he appeared in the supernatural film ‘The Uninvited’ and Fritz Lang’s film noir ‘Ministry of Fear’. He also travelled with the United Service Organisation South Pacific troupe the same year.
In 1945, he starred as an alcoholic writer in ‘The Lost Weekend’. He was applauded for his performance and won several awards, including an Oscar. His contract was rewritten and he became Paramount's highest paid actor.
Thereafter, he starred in several pictures like ‘California’ (1947), ‘The Big Clock’ (1948), ‘Alias Nick Beal’ (1949), ‘A Life of Her Own’ (1950), etc. He continued as the lead man of Paramount till the early 1950s.
In 1951, he acted with Gene Tierney in ‘Close to My Heart’ as a couple trying to adopt a child. His performance in the film was critically acclaimed. The same year, he also acted in ‘Circle of Danger’, set in the UK.
In 1952, he acted in ‘The Thief’ – a challenging role with no dialogue. In 1954, he starred opposite Grace Kelly in Hitchcock's only 3D movie, ‘Dial M for Murder’.
After leaving Paramount, he dabbled in direction. His directorial debut was a Western film called ‘A Man Alone’ (1955). This was followed by a crime drama, ‘Lisbon’ (1956).
He also successfully ventured into television. From 1953 - 1955, he starred in the CBS sitcom ‘Meet Mr. McNutley’ (later called ‘The Ray Milland Show’) and from 1959–1960, he featured in CBS detective series ‘Markham’.
In 1966, he played the lead role in Broadway ‘Hostile Witness’ directed by Reginald Denham. The play was fairly successful and in 1968, he reprised his role of Simon Crawford, Q.C. in a film of the same title, which he also directed.
In the early 1960s, three of his films became cult classics: Roger Corman’s ‘The Premature Burial’ (1962) and ‘X: The Man with the X-Ray Eyes’ (1963); the third was his self-directed sci-fi drama ‘Panic in Year Zero!’ (1962).
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In the late 60s and the 70s, he returned as a character actor, and featured in cult classics like ‘Daughter of the Mind’ (1969), Love Story (1970), and its sequel ‘Oliver's Story’ (1978).
Towards the end of his career, he appeared twice in ABC’s ‘Hart to Hart’, two episodes of ‘Columbo’ in 1971 and 1972, and guest starred in the pilot episode of ‘Battlestar Galactica’.