Skee-Lo - "I Wish"
This is right up there with the Fresh Prince theme song in terms of raps that at least one girl at every sorority party knows all the words too. Here's the main thing, though: Skee-Lo's "I Wish" is depressing. Like, read the lyrics. Dude is a mess, and he's totally unhappy with his life. So why does this song sound so fucking happy? This is like sitcom rap, tackling major issues in an easy, digestible way. But you know what? Sometimes we need sitcoms, and maybe we need more sitcom rap, because "I Wish" still hits us on some relatable, every day life struggles kind of shit, without being too heavy.
P.S. Where is Skee-Lo?