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My first ever epic drop was Dazzling Longsword off one of those woodpaw guys while doing a quest in Feralas. I had just hit 40 and blew all my gold on my mount the day before. I took the gold that I made off the sword (maybe 50g?) and bought Recipe: Savory Deviate Delight with it. I leveled fishing and found that @ level 40 I had no problems fishing inside of Wailing Caverns. I sort of stopped leveling at the time just to recoup the gold from buying the recipe (which took no time at all because cooked Deviates were going for 10g/stack at the time on my server). I ended up having no problems paying for my mount when I hit 60. :)
My T4 helm token. Best day ever. I still have it in my bank.
Probably the most epic loot I almost got was during the Hallow's Eve event this year on Halloween. I had payed nearly 10,000g bribing people to gain the items needed for achievement, so I was pretty much done of farming the Headless Horseman. On Halloween night after I got home from work I logged on and talked to my friends on vent. We all were really bored (one guy was really drunk) so we decided to see if we could 4 man the boss, just for fun. We summoned the guy 3 times, downing him easily, and finnaly we were up to our last summon. We got the Headless Horsman to the second phase, when all of sudden, trick or treaters knocked on my door. I immediately tell the shadow priest "QUICK HEAL, I GOT TRICK OR TREATERS!". So I rush down and open the door, but the teenage trick or treaters had already left. I ran upstairs fast enough that we downed the boss, AND HE DROPS THE HEADLESS HORSEMAN MOUNT! We all were screaming OMG and LOL FINNALY. We all decided for everyone to need after 2 minutes of arguing and just as I hit need, my power shuts off. I checked outside and apparantly the teenage trick or treaters got revenge and cut my power cables with some hedge clippers. My drunk friend calls me on my cellphone and tells me he got the mount. I was anrgy! The the next morning my friend is sent to the hospital for some kidney problem. I decided to visit and I say to him "Dude you were almost pushing up daises." then he says "At least I have the Headless Horseman mount". That was probably the most epic moment for me related to WoW, where I hadn't won.
My epic loot was the Web Cocoon Grips from Naxxramas, we put up a fight pretty hard for the roll, both me and two more needed on it, but with only 3 points over the second one I won it, that was pretty hard-epic!
I remember when i ding'd 60 2yrs ago, i went 2 a zg raid, and i won the dagger from first boss, wtih 10 other ppl rolling for it ! 60 and first epic hi end loot in same day ! woohoo, i was soo happy ;)
Reins of the Raven Lord. Absolutely no contest. No drop or item within the entire world makes me happier than that big beautiful chicken, and let me tell you it did not come easy. Four very awesome guildies put up with running Heroic Sethekk once a day for weeks on end... and when it finally dropped, they all passed without a moment's hesitation. I've been riding the stuffing out of that thing and I've never grown a bit less excited about it. I should add that I play a Tauren. The thing is huge. I bowl over the entire AH with that tail when I turn.
Probably Skullflame Shield...though, does it count if someone else snags it? :(
Since Wrath came out, my friends and I have been farming heroics. We decided to try for Skadi's timer and we wiped till we had respawns. On our last attempt, we nailed it perfectly! I was so happy, I almost forgot to loot my emblem. :P
I remember how much I wanted the vexing cane from ZF on my mage, I kept joining ZF groups and never say it drop. Then when going through my inventory I saw it there. I must have not been paying full attention to the loot in one of the runs. It was just really funny to have been struggling to get it and then realizing I had it allready.
Another most epic drop was the Robes of Transcendence back from Nefarion. My guild was the 3rd alliance guild on the server to kill him yet the robes would not drop! We killed him week after week and nothing! So finally I almost gave up and almost spent dkp on the MC robes, but that week the Robes of Transcendence drop and I freaked out! I was saving up dkp so much so I knew I could have them first! I was one of the only priests on the server to get them at that time. Only big time guild priests had them and I was freaking out. It's funny cause it was a huge upgrade for me as well since I was still in devout robes! Talk about upgrade!
I started running Kara last December, with the goal of trying to get http://www.wowhead.com/?item=28590 each time I went. I lost every roll when it dropped for 7 straight months. I even lost the roll when I finally did get it. The raid leader didn't have the heart to give it to the other healer who just started that week, who decided to bow out to let me have it.I also didn't win the roll for http://www.wowhead.com/?item=28771 until -after- I had managed to get http://www.wowhead.com/?item=32963. Kara just hated me for some reason.:D