1) No Diggity - Blackstreet
No Diggity is one of those songs I always forget about, and that is totally unfortunate, because it's an amazing hip hop anthem. I mean, Dr. Dre uses the word eargasms. Not everyone can pull that off. Not to mention there are an EXCESS of overalls in the video.
2) Jackson - Johnny Cash and June Carter
I wish this song was about Jackson, WY, one of my favorite places in the whole wide world. But I guess Jackson, MS makes more sense (Although it's never specified). But the location is unimportant, it could just as easily be called Dallas or Nashville. I love that it combines revenge with a "anything you can do, I can do better" attitude. Both halves of the couple are going to find someone new and they are going to do it better. Isn't that the best kind of revenge?
3) Tears Dry on their Own - Amy Winehouse
Amy Winehouse made straight-up terrible life decisions (Drugs and alcohol aside, all that teasing cannot be good for your hair). But the girl could sing. Amy had a lot of really good songs but I like Tears Dry on their Own for one line: "I'll be some next man's other woman soon." This is is a break-up song, she could have easily written something about finding someone better, but instead she wrote about finding someone better and becoming their other woman. Ballsy. You could throw a lot of psychology words at that, I'm sure. But I'd rather enjoy the bluesy-soulness of it.
Bonus: What's your Fantasy - Ludacris Because it dirty and gross and sometimes that's exactly what you are looking for in a hip hop song.