For me it would be Giantstalker's Breastplate. It was the very first epic item I looted, and it felt very much like an epic achievement back in the day.
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My most epic was winning the rolls for 3 items in my first Kara run!
The next most epic drop was my First Epic, Bladeangel's Moneybelt. I was so excited when i got it!
i remember back in the day when Bloodrazor was a hard drop, sold it for 350g
It's my Grim Totem Ghost Wolf. I tamed him, with the help of 3 random people I convinced to help. Thanks Peacecuffin, Korruptedgrl and Draenicsham of Llane.The VERY NEXT DAY, they patched it. I may very well have been the last to tame the wolf. EPIC.
My most epic would probably be, if it counts, when I took my Pally into Kara at 69; dinged 70 and walked out with 9 epics. (2 for offspec).
The most epic loot i have ever gotten would have to be my Toy Train Set. When me and my guild are running 25man Nax i always put it down so while my guild leader explain the fight, everyone is constantly going CHOO CHOO! and half the raid gets %^&*eded off while the other half are dying of laughter, and the best part is it was only 250G! the only down side is the 30minute cooldown, but the train is down every 30minutes.
I really enjoyed just getting the loot from my first MgT run. That was the first level cap instance i ever ran and i really enjoyed it!