Macksheath said:
Hard to say. Most bosses nowadays are just tutorials.
So...as someone said, Buzz from Spyro; Year of the Dragon. I found it near impossible to dodge that spinning thing he does.
Ahaha, God, that brings back memories. My little brother and I used to play this game all the time as kids, and we used to get so pissed off with this one boss. We finally kicked his ass, and my brother was so happy he literally ran out of the room screaming with joy...He's an interesting kid.
OT: Hmm...kind of hard to decide on one specific boss...I'm going to go with the spider-thing from Devil May Cry, simply because of the amount of effort it took to kill the damnable thing. At the time, I wasn't exactly experienced with either the game or the controls, and would frequently find Dante performing actions I had not actually ordered...