Jujin my first character ever. He was born in Elona, and naturally became a Barrage ranger. When PvE skills were first introduced, I gave him "SY!" and everything turned out all right. Nowadays, I almost never use him except for the occasional Zaishen or UW trapping. He was the first one I took into the Prophecies campaign and he was the first one to beat both Prophecies and Nightfall. His monks still have crappy Mending builds from years ago--and I plan to keep them just for the sentimentality.
Advent is my runt, mostly made because I didn't have a warrior at the time and I wanted to play through Elona again. I leveled him up to level 20 then farmed a little bit with him, then forgot about him totally. I used him initially to run Sanctum Cay, but then I realized how nub that was and made him a chest runner in FoW. Once EotN came out, he became my Destroyer Core farmer and has been ever since. Again, I almost never use him. For the sake of actual PvE gameplay, he mostly runs an Erf Shakur build.
I made Anguish back when I realized how badass Paragons were (and are). Naturally, like most of my characters, he was abandoned at a low level until "Save Yourselves!" was introduced. Since then, he has become my Imbagon and my 3rd most played character. He has never beaten a campaign, but has traveled to the corners of Tyria. He is the one I use for most of my everyday PvE happenings, including FoW, UW, DoA, and basically anything but pure vanquishing.
Chaos Spark was created immediately when I first bought Factions. However, he never got very far in the campaign but still remains one of my favorite characters with the coming of the new Xinrae's Weapon (although I use him next to never). He has been used as the Rt/W UW farmer, although that was years ago. These days, he likes to take up a character slot and basically farm birthday presents and collect dust.
Defect is my best friend. Born in Cantha, he was the first one ever to complete it. I use him the most of any character for PvE. He likes to run the Triple Necro Vanquish or Discord Spam to vanquish the world and get protector for all 3 continents. He has been everywhere in the world, with all 3 explorer titles 95+% complete. He has run everything from the UW 55/SS, to the solo 55 SS, and the SV boss farmer. I use him to farm for cash just by the steady inflow of vanquishing cash. If I am not PvPing, then you will find me on him, most of the time. I love necromancers!
Faithful was born in Cantha, and she is a fire nuker. Generally, she uses SF, but on DoA Cryer teams she runs Ether Prism. Most of the time, I don't play her unless I really want to do a full tour of DoA. She has had some hot times, sizzling up AB, FA, JQ, and other PvP areas with various bomber builds to mostly nuke shrines. In AB and JQ, I especially use her with Assassin's Promise and Meteor Shower and some other spells to spice up a battle. Other than that, she is also a birthday present farmer.
/Hope Once More
My main on my second account, Hope is mainly a bonder for when I use my dual-client Discord Spam variant (use two accounts on the same computer with 3 Discord necros each, log into the explorable area, and log off on one account so the heroes follow the 1 human left. This way, you don't have to run around with two separate people), but otherwise she runs ZB and Consume Corpse (Actually great in PvE). I try to use her as much as I can, although it's tedious since I don't have many skills or items unlocked on the second account.
/Things Unseen - PvP
Things is usually a monk, and my only PvP character. I mostly run HA and TA on him, although lately I've been dabbing into GvG. He runs Life Sheath in TA and RA, RC in HA, and often WoH in GvG. Besides a monk, Things is most often a mesmer, and has in the past been basically anything imaginable. I use him occasionally as an Assassin in HB, although I've always had trouble in HB.
Twilight was the second character that I ever made, and I made him just after I beat Prophecies on Jujin. He is the monk I use whenever I need to monk on my primary account. He has fallen out of use since the creation of Hope, but he is still a valuable character to me. He is always a HB when playing normally, although there was a period when I used him specifically for 55ing. He stayed mostly at Bergen to farm the undead with SoJ. Since then, he has gained quite an arsenal of builds that I can possibly run and places that I can farm.
An Assassin by nature, Opressed is basically used for my utility in PvE. Yes, I realize that there is a misspelling in his name, so here's the story: Opressed was to be a survivor, so I spent an excruciating amount of time leveling him up. I realized the misspelling at level 12, but by then it was way too late for someone as lazy as me. I continued to level him up as a survivor, but he was killed at level 18. :( Nowadays, when I'm bored, I use him to permaform TPK and also I run Droks as a permaform from time to time. I never have and never will use him for PvE play--i should hope we all know how much sins suck in outside of PvP.