9. De La Soul "Millie Pulled a Pistol on Santa" (1991)
Album: De La Soul is Dead
Producer: Prince Paul,De La Soul
Label: Tommy Boy
De La Soul came in the game on the stoned, free-spirited fun of 1989's 3 Feet High and Rising, but the Long Island trio (and their producer Prince Paul) began to feel trapped by the neo-hippie image that resulted. Their sophomore album De La Soul Is Dead is a very deliberate divorce from "Daisy-Age" antics of the first album, infusing their creativity with darker, weirder themes on songs like the drug addict character study "My Brother's a Basehead" and the heartbreaking story of "Millie Pulled a Pistol on Santa Claus." Here, a troubled Posdnous gets close enough to his court-appointed social worker Dillon to find out that he might be molesting his daughter Millie. Problem is Dill's considered an upright citizen in the community, so no one believes Millie. The story gets bloody quick as Millie, lonely and pressed for a way out of her personal hell, pulls a gun on Dill and publically pops him right in the middle of his stint as a shopping mall Santa.