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High Sierra, starring Humphrey Bogart, is one of the great classic gangster films, continuing the traditions of the 30s (when the gangster film was at its peak) but dabbling with romanticism and stylized cinematography more characteristic of the film noir genre, which wasn't quite formed by 1941 but soon would be. The script, in fact, was co-written by John Huston, who also wrote and directed another formative noir film, The Maltese Falcon, in the same year.
Opposite Bogart -- and earning top billing, interestingly -- is the tough-as-nails Ida Lupino, who not only did great acting work in crime films but became one of Hollywood's first major female directors when she started making them herself in 1949.