12. "Cleanin' Out My Closet" (2002)
An innately combative MC, Eminem dreamed up his alter ego Slim Shady so he could unload on the world with impunity – morality police, music critics, other white rappers. But his true-north antagonists have always been wife Kim and mom Debbie. And of all the songs about his mother – both absurd and apologetic – "Cleanin' Out My Closet" is the most deeply affecting, even becoming a Top Ten pop hit. DJ Head's syncopated, almost delicate drum loop darts around the dark, spare instrumentation (bass, guitar, keyboards played by co-producer Jeff Bass), while Eminem excavates a lifetime of debilitating parental emotions. The song's tone nimbly fluctuates, especially with the haunting "I'm sorry, mama," chorus. Finally, there's the climactic betrayal – when his mom, according to Em, tells him that she wishes he'd died instead of his uncle/best friend Ronnie (who committed suicide in 1991). Eminem barks his chilling reply into the void, "Well, guess what? I am dead – dead to you as can be!" In 2014, fellow Detroit native Angel Haze was inspired by to revive and revise "Cleaning Out My Closet" to tell her own tale, one of being sexually abused as a child. "I was so angry," she told The Telegraph. "It was like catharsis to listen to [Eminem]."