3. Johnny Cash, "Hurt"
Johnny Cash made one of the saddest, most heartbreaking videos of all time before his death. For his cover of Nine Inch Nails' "Hurt," the iconic singer is seen in a gothic home surrounded by his wife June Carter Cash and fruit in various states of decay. Images of him in the present are intercut with visuals from his past and his youth as the singer — who would pass away seven months later — reflects on his own history.