When James Caan died at the age of 82, Hollywood lost an icon. From his collaborations with Francis Ford Coppola to iconic roles in “Misery” and “Elf,” Caan was an essential part of Hollywood history in the second half of the 20th century. While he never quite achieved the stratospheric stardom that many predicted for him after “The Godfather,” he remained a major presence in Hollywood up until his very last days. Alternating between cool leading man roles and character parts with ease, Caan worked with many of Hollywood’s top directors and made classic films in every decade of his 50 year career. As the world mourns his death, here are nine of his best roles that are always worth revisiting.