Probably T4 helm way back in the day. The token would always refuse to drop and then when it did, I'd lose the roll. Finally got it though! :D
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My T5 shoulders for my priest -- I wanted my priest to have wings sooooo badly. Beyond that, probably my first long pet grind which was the crimson whelpling.
I rolled 100's for need and greed in heroic nexus for the war mace of unrequited love and the orb xD it was pretty awesome.
Shoulderpads of Absolution, the pimpest looking cloth shoulders ever. I was pretty thrilled about them!
i'd say my most epic one was when i went after the headless horseman for the first time and got his helmet, sword, and a ring i could use while we were there.
Most epic drop ever was when I got my flameskull shield. it's been a long time, but that was Hawt.
I hit 80 a few days after launch of Wrath and I go to fill my last glyph. I decide to use Glyph of Spirit of Redemption, sound interesting at least. So I pop it in and take off for our first heroic. My party and I are in Heroic Halls of Lightning and we are pulling to Volkhan. We pull two mobs groups. Being fresh 80's I'm not sure we can handle it. Low and behold I die from healing aggro and by Spirit rises to heal the party. The new glyph proc'd so much, I must have been alive for 45 seconds total. Flash Heal Flash Heal Flash Heal Circle of Healing Flash Heal. There was no way we could have won if I ironically hadn't died. People now want me to heal Heroics all the time because I never let people down, and if I do I rez them back up. The feeling of keeping people's spirits high is Epic
One of my most epic moments that just spurred on me was when I was a Rogue in pre-BC and was actually enjoying my leveling up. I was pretty nub back then, so I took LW and skinning for professions. Long story short, I was always broke, but I saw Krol Blade in the auction house and I just freaked out at how awesome it would be for my Rogue! Since I was broke, I decided to try and make money for it. After at least 2 weeks, while getting the last 50g, it freaking dropped for me! I suppose hard work pays off in special ways sometimes =]
Rogue T1 shoulders. We were running MC for months without them dropping and a friend got them before me. Later the same night he got the T2 shoulders. After a quick back and forth with a GM about a "loot mishap" (and the approval of our guild master), I had the T1 shoulders waiting in my mailbox! :)-Vix
Definitely the Reigns of the Raven Lord. A Tauren Druid, on a Raven Lord, with the size increase from Potion of Giant's Strength? I terrorized downtown Orgrimmar for quite some time.
The most epic drop? It hasn't dropped yet. I'm clocking well over 5k kills on 3 characters, accumulated over a period of 1 year while going for the Azure Whelpling. That little blue thing has become my everest, my Moby *!@#. I'll propably pass out if I ever actually get it.