Album: The Don Killuminati: The 7 Day Theory

"Look for me, lost in the whirlwind." It doesn't take a degree in psychiatry to read "Me and My Girlfriend" as a window into the chaotic last year of Tupac's life. Beset by enemies both real and imagined, and both external and internal to his own clique, 'Pac raps with evident distress about his "girlfriend," who is, of course, not a flesh-and-blood human, but a gun. Nas had done the gun anthropomorphism thing earlier in the year with "I Gave You Power," but 'Pac's manic energy and tragic death gave the concept even more poignance (plus 'Pac didn't insult his audience by explaining the metaphor—"It's like I'm a motherfucking gun"—at the top of the song). It's an angry track, fueled by a desperation that in hindsight feels heartbreaking, giving the distinct impression that one of the greatest musicians of the 20th century died without much in the way of true friends. —Jack Erwin