Hmm...probably when I finally got my Libram of Avengement on my paladin (before he went prot xD)...I ran H BF so many times I was exalted before it finally dropped - somewhere around my 17th(?) run or so it dropped...prot pally that was in there rolled need and I pretty much flipped on him, but outrolled him with a 99, haha. Anywho, if you're talking epic epic, gotta say t'was when I got my Shard of Azzinoth on my rogue...finally..mmmm....Mut happiness! :D
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My most epic loot was my first swift flying mount. It was a grind, but worth every copper.
I'd say my most epic drop, well it wasn't a drop, but Recipe: Dirge's Kickin' Chimaerok Chops, no one runs AQ or BWL nowadays (this was pre-3.0), but after a few months I'd got together enough Brood rep and managed to put together just enough people for a BWL run. It was the last cooking recipe I didn't have that I can get, was a great feeling to finally get every cooking recipe in game, especially since this last one is epic.(I would have said Tome of Polymorph: Turtle, but 46 ZG runs and so far no drop still. I'll be happy when (if?) I ever get that one)
I started this game while it was in beta form so i have some playing time the most items ever dropped at time that was epic was Orb of Deception i had 4 of them drop in Eastern Plaugelands in 2 days. Also in Felwood while just grinding Kang the Decapitator dropped the same day the Orb dropped in my hands. I say i was darn lucky being a Paladin Kang was only good in AH it sold within 15 minutes.
ScholomanceThat day, i was just walking around Stormwind being bored and i was reading the guildchat. They said that going too Scholomance would be a cool idea. But they only needed a healer... I'm a priest so i whispered him. Then i got summoned too the stone infront of the dungeon. I tought: "Woah, let's slaughter some undeads (evil laugh)"Then we entered the dungeon killing some mobs and dancing around them.. i saw the zombie room (at the end) and i said: "yey, i love these zombies, it let me feel i'm in Deadrising." i pulled the zombies for fun and ran in circles outside. So we cleared all the zombies inside and all of a sudden... i saw a purple icon popping up. I saw the item and "OMFGWTFBBQZOMGROFLZORCOPTER?" IT'S THE SKULLFLAME SHIELD ! THE AWESOMEST SHIELD OF THE WHOLE WORLD OF WARCRAFT!11 :O I was #%^@&*! happy and spammed the guild AND party chat with loads of craptalk. Even before i rolled, lol. So i pressed the greed button and the rest of the groupmembers did the same. And guess what? I WON! :DItem: Skullflame Shield best looking shield ever >:] Proof: Click HereXéon
My epic loot would probably have to be the Crusader Enchant I grinded for my girlfriend. Everyone told me it would take days, weeks, months even to get. But her birthday was coming up so I was determined. (Don't worry, I got her a RL gift too. XP) Anyways, I went up to those Scarlet people and started pounding every one I could see. After maybe, a dozen, the recipe drops. I couldn't believe it, so much so I sprung the surprise early. XD
My first blue i ever got, ever was the speed steel rapier, of a scorp in Tanaris. sadly me being a damn nub sold in in the AH for 5g... i know. (taught me the meaning of f epic(failure))
I farmed so hard for that damn headless horsemans mount, I was so happy when it finally dropped