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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 initially appeared in crime films or dramas such as Blonde Venus (1932) and She Done Him Wrong (1933), but later gained renown for his appearances in romantic comedy and screwball comedy films such as The Awful Truth (1937), Bringing Up Baby (1938), His Girl Friday (1940) and The Philadelphia Story (1940).Along with the later Arsenic and Old Lace (1944) and I Was a Male War Bride (1949); these films are frequently cited as among the all-time great comedy films.He is remembered by critics for his unusually broad appeal, as a handsome, suave actor who did not take himself too seriously, possessing the ability to play with his own dignity in comedies without sacrificing it entirely.His comic timing and delivery made Grant what Premiere magazine considers to have been "quite simply, the funniest actor cinema has ever produced".Hitchcock admired Grant and considered him to have been the only actor that he had ever loved working with.Towards the end of his film career, Grant was praised by critics as a romantic leading man, and received five Golden Globe Award for Best Actor nominations, including Indiscreet (1958) with Ingrid Bergman, That Touch of Mink (1962) with Doris Day, and Charade (1963) with Audrey Hepburn.

He was presented with an Honorary Oscar by his friend Frank Sinatra at the 42nd Academy Awards in 1970, and in 1981, he was accorded the Kennedy Center Honors.

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.

Grant claimed to be the first freelance actor in Hollywood and the lack of central contract helped increase his salary to 0,000 per picture.

The film was a box office bomb and prompted Grant to reconsider his decision.