Monica - "Angel of Mine"= All because this girl I had a major crush on was in my math class (6th grade) singing the song, and everytime I hear it, I think of her. Now unfortunately.
Boyz II Men - "On Bended Knee" = probably my most fav. song of theirs just cuz of being girl crazy every year.
Will Smith - "Gettin Jiggy Wit It" = all because the video is so memorable and BWS cassette was givin' to me by my brother cuz he got the cd/cassette set. And plus, I "performed" it front of my music class, well most of them got up to dance behind me. lol
2pac - "Keep Ya Head Up" = it was the first time I heard 2pac legit, back in 2001. I was chillin with my dad and bro, and Pac was on BET's Top 5 Countdown. That song played and I instantly downloaded it, then brought the 'Greatest Hits' and been a fan ever since.
I've got so many really, as I'm sure many of us do. Like Dr. Dre's "Keep Their Head Ringing" was the first time I would learned that 'funk' wasn't a bad word.