There are so many clickies I keep on me these days, it's ridiculous. I've accumulated so much over the years.
A noteworthy accomplishment is the massive collection of illusion clickies in my keyring. I'm sure many bards and rogues out there could share similar stories of how it took forever to farm such and such illusion, as it was a common goal among both classes to obtain them all.
The halfling illusion mask made me love Chardok though. I spent a lot of time down there swarm kiting in the mines while camping Overseer Dal`Guur. I'd farm other named in the zone while waiting on respawns. I lived down there at times... I'd use Haggle Baron Dry`dn to sell all the gems and such that I'd collect during my killing sprees, and then, I'd run around next door to visit Vault Master Shu`zo in the bank. Wonderful zone.
The next logical step was farming Preserved Chokidai Vocal Cords in the palace library. I spent a lot of time in there off and on, collecting multiple Anklesmashers without ever seeing the vocal cords drop. It wasn't until years later that I finally was able to add the vocal cords to my collection. Vocal cords probably took longer than any other item in the game for me to acquire. But, while down there, I would kill the royals multiple times in a day, collecting their drops, and I even pulled the Overking to the entrance a few times for guild members working on their cleric epic weapon. Of course, it was trickier back then as the mobs still presented a challenge and even gave me experience, and bards didn't have a high enough pick lock skill to open the door down to the library at the time.
Songblade of the Eternal and Rapier of Somber Notes were also memorable. I was called in the middle of the night on a weekday after I had already gone to bed... probably 1 or 2 AM, asking if I could log in and come loot the songblade that dropped in Plane of Time (by a guild other than my own, mind you). The same guild a year or so later had an extra rapier drop, and I received another tell asking if I could come loot it too. I, of course, still carry around the rapier for its clicky effect. I replaced my songblade in inventory at the time with it, as the rapier has the shorter cast time and the songblade also required you to equip it for the clicky at the time. I miss when this was more of a common occurrence across people on the server.
Some other fun and memorable items I keep on me are things like Gnomish Troutshocker, Zatozia's Pail of Rainbow Sherbet, Zatozia's Pail of Chocolate Ice Cream, Docleaf's Shattered Shard, Lepracon's Pot of Gold... and probably some other stuff... from the many events and contests Zatozia held. I miss those so much. They were tons of fun both in game and on the forum. Poems, art, screenshots... it was enjoyable seeing the community's creativity. Glad to see some of that stuff happening on this site here.
Okay, I could probably go on and on, but Rorce said "an item" and I've gone a bit overboard, so I'll end it here.