James Caan and Billy Dee Williams star in Brian's Song.

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It's the movie that makes even the toughest guy cry, and it set the standard for the many heartfelt sports movies that would follow (despite being originally made for TV). The fierce bond between Chicago Bears teammates Gale Sayers (Billy Dee Williams) and Brian Piccolo (James Caan) is an unlikely one—they're competing for the same position and defying a race barrier still prevalent in the film's 1960s setting. But when Brian is diagnosed with terminal cancer, we see how strong, and vulnerable, real men can be.