EQ - Plane of Fear, Sometime in 2000 with ~80 other semi clueless saps. Wipe for several hours at zone in and waited another 5 hours in order to get my corpse with all my gear.
WoW - Strat and UBRS and then ZG, first "real" boss I ever killed was the Raptor boss.
Kara I see here alot, best raid ever imo. That was the first raid I ever led.