Lil Zane

The first rap song I liked was Gangsta's Paradise, which my dad would play for me and be like "see, being a gangster isn't a good idea. Stay in school nicca." Outside of that my parents weren't fond of me listening to any
modern "worldly" music at the time, so I wound up sneeking the radio into my room and listening to soft rock/pop till I fell asleep. Later a friend introduced me to Britney Spears and Eminem, both of whom I loved. This was like in 1999. Later I fell in love with the Marshall Mathers LP, which is an undeniable classic as far as I'm concerned.
But the first time I really fell in love with rap is when I heard Tupac for the first time. I was in Ohio with my AAU basketball team, and everyone had walkmans and CDs except me. So while one of my teammates was sleep I stole his walkman and listened to the first disk of Until the End of Time. At the time I didn't know it was a posthumous release, I just liked what I heard. That first disk has some definite bangers on it, and I was most impressed with Lil Homies at the time lol. Later I wound up exploring Tupac more, and I also consider him to be the greatest rapper of all time. And it's not that he was the greatest lyricist or rapper, but he was the greatest
rap artist by far. He forced the establishment to look at rap as art.
For awhile I was heavily into the gangsta posturing of mainstream rap. An older friend of mine who was on the varsity basketball team (I was JV) would drive me home from practice, and he had tons of rap CDs. So he introduced me to DMX, Nelly, Bone Thugs, and everything else that was popular at the time. In fact my tastes didn't really change until I heard Kanye West in 2003; while some critisize him, he definitely introduced me to artists like Common, Mos Def, Talib Kweli, The Roots, Dilated Peaples, etc - for which I'm greatful lol. After that the dam essentially broke as I went back and explored the roots of the genre. Even to this day I'm still looking up classic albums, trying to digest as much as I can. I heard The Imfamous and 36 Chambers for the first time this year; I had heard singles like Shook Ones before, but never the entire album.
Now I'm into a lot of underground, "backpack" stuff like Brother Ali and Atmosphere as well as underground alternative stuff like MF DOOM. And I can still bounce my head to TI when in the mood :p