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Grant's role is described by William Rothman as projecting the "distinctive kind of nonmacho masculinity that was to enable him to incarnate a man capable of being a romantic hero".He played a suave playboy type in a number of films: Merrily We Go to Hell opposite Frederic March and Sylvia Sidney, Devil and the Deep alongside Gary Cooper, Charles Laughton and Tallulah Bankhead, Hot Saturday opposite Nancy Carroll and Randolph Scott, When his contract with Paramount ended in 1936 with the release of Wedding Present, Grant decided not to renew it and wished to work freelance.Having established himself as a major Hollywood star, he was nominated twice for the Academy Award for Best Actor, for Penny Serenade (1941) and None but the Lonely Heart (1944).In the 1940s and 1950s, Grant forged a working relationship with the director Alfred Hitchcock, appearing in films such as Suspicion (1941), Notorious (1946), To Catch a Thief (1955) and North by Northwest (1959).Grant was married five times; three of his marriages were elopements with actresses—Virginia Cherrill (1934–1935), Betsy Drake (1949–1962) and Dyan Cannon (1965–1968).He has one daughter with Cannon, Jennifer Grant (born 1966).The contract stipulated Grant's weekly salary along with room and board, as well as dancing lessons and other training for his profession until the age of 18.There was also a provision in the contract for salary rises based on job performance.
Upon learning that his son was once again with the Pender troupe, Elias co-signed a three-year contract between his son and Pender.
Biographer Richard Schickel claims that Douglas Fairbanks and Mary Pickford were aboard the same ship, returning from their honeymoon, and that Grant played shuffleboard with him.
He was so impressed with Fairbanks that the actor became an important role model.
In 1999, the American Film Institute named Grant the second greatest male star of Golden Age Hollywood cinema, after Humphrey Bogart.
Grant's biographer Graham Mc Cann mentions that Maureen Donaldson, a lover of Grant in the 1970s, claimed in her book that his mother "did not know how to give affection and did not know how to receive it either." Due to alienation from his parents, he found it difficult to socialize and had a nervous disposition.
He enjoyed the theatre, particularly pantomimes at Christmas which he would attend with his father.