So here are the first five songs I think you should check out. I can't say you will like them all, but if there is a song (or songs) that you enjoy, that'll help understand which direction to take you next :).
Jurassic 5 Jurass Finish First This song - and album - reminds me of high school the most of any of these songs. I'm not even sure I could call this my favorite track on this album, but I think it lends itself more to an introduction.
Brother Ali Fresh Air Brother Ali is not for everyone, but I enjoy him quite a bit. This song, specifically, just puts a smile on my face whenever I listen to it. So super positive.
Binary Star Honest Expression This song is in my top 5 hip hop songs; it speaks to the mainstream hip hop world and says, "This is hip hop." Plus, a bad ass Bruce Lee quote to get you in the mood - like built-in foreplay!
Notorious B.I.G. Juicy This wouldn't be any kind of "lesson" if I omitted Biggy. Some of his songs focus on drugs, women or fucking; what I really enjoy about this song is the crux is positivity - changing your life, and going from nothing to something.
Black Eyed Peas Hot BEP put out two albums before they got famous, and they were both delightful (after that, pure shit). I picked this song because of its sexiness; Kim Hill does the chorus, and her voice is just so sensual.
This is just to show off some of the more "unique" things some artists do.
Blackalicious Chemical Calisthenics Truthfully, I don't really like this song, but it's really creative. He just talks about chemistry - I couldn't think of a bio song for you, so I figured this would be close enough :).
Binary Star Wolfman Jack I just couldn't resist including this song, even though I already mentioned one of their songs above. Such cool story-telling...if you pay attention to the lyrics, you will get goosebumps.
Beastie Boys Girls Super simple lyrics, a fucking vibraphone through the entire song(!), playful, and funny.. This song reminds me of middle school, even though it came out many years before that.