(Photo by New Line/courtesy Everett Collection)

James Caan rose to prominence with the 1971 gridiron tearjerker Brian’s Song, portraying cancer-afflicted Chicago Bears halfback Gale Sayers. Song was the most-watched TV-movie ever at the time, and earned Caan a Leading Role Emmy nomination. He matched that a year later with an Oscar nom for his performance as the reckless Sonny Corleone in The Godfather. Though those were the only major movie and TV nominations of his career, Caan would impact and shape the industry for decades, including starring in Michael Mann’s directorial debut (the stone-cold Thief) and Wes Anderson’s first (Bottle Rocket), putting a page in the book of great Stephen King adaptations (Misery), and appearing in Jon Faverau’s critical and commercial breakthrough, Elf. Caan appeared in almost every season of Las Vegas, and his final released project was 2021’s retirement community-set romantic comedy Queen Bees.

We look back and celebrate on Caan’s seven-decade career with his best Fresh films.