The second rap song ever nominated for Record of the Year was Coolio's "Gangsta's Paradise," at the 1996 Grammys. It's a pretty catchy song, and has some memorable lyrics, even if Coolio isn't the most charismatic MC to grace the stage (That hair, though). The nod seems reasonable enough, until you realize that 2Pac and the Notorious B.I.G. were both denied awards that very year (for "Dear Mama" and "Big Poppa," respectively). Even Skee Lo's "I Wish" aged a little better than the Coolio classic. That's saying something.