Year: 2003
Director: Mark Romanek

Cash's cover of the Nine Inch Nails song about depression, loneliness, and addiction is haunting on its own, but when you add his worn face, his Nashville home, the House of Cash museum, and archival footage of his life (both highs and lows), it makes "Hurt" all the more profound. Consider that June Carter, his wife of 35 years, died shortly after appearing in the video, making Cash a widower until he died just four months later, and it's impossible to not get choked up by this one.

YOU AUGHTA KNOW:
Trent Reznor initially thought the Cash cover of his song might be too gimmicky. After he watched the video, he gushed: "Tears welling, silence, goose-bumps... Wow. I just lost my girlfriend, because that song isn't mine anymore."