Hmmm... If you just want the strangest character I've ever played in terms of backstory and such...
Hmm, I'm known for playing strange characters, so I have a fair amount of them to pick from. (warning, I'm prone to going into first person when I tell my stories... It's easier for me than saying "my character" all the time) And since multiple DMs I play under tend to do a one-on-one "backstory" session where you effectivly play a 0th level nothing for the duration, my characters are fairly well fleshed out.
Ok, ya know the sorta cliche (It was done in CT:HD, for example) story of a princess who, for one reason or another, runs away and disquises herself as a boy?
I sorta did the oposite one time.
The backstory was my character was a prince set to acend to the throne soon. My father was very ill, and all atempts at cures had failed. The best healers said he would probably die within the next few months.
Problem? Several, actualy. First of all, my younger brother (just barely 17, my character was almost 19 at the time) wanted the throne. My character had no real desire to rule anyhow, so this wasn't a huge deal you would think, except for the laws of the area... I couldn't just give the throne to my brother, it didn't work that way. My character had actualy always wanted to become a wizard, but the laws of the land forbid the heir to the throne doing such things... it was a "risk", for one, and magic was... sort of frowned on in that kingdom. Nevertheless, my character had sorta "persued" the idea in his spare time... he had even managed to make friends with a few wizards of the local, semi-secret wizards "guild".
Anyhow, my father was getting worse. The healers were starting to say it could be any day now he died. It was then that a friend of mine in the palace, who was close to the personal attendants of my brother, started to hear rumors. My brother apparently had a plot to have me assassinated before my father died. In the turmoil surrounding the current kings death, no one would really have time to question events at first, and once he WAS king, he could get the situation under control.
Figuring I didn't have long before my fathers death, I started figuring out a way to get out of dodge with my life, if you will. Of course, running away wasn't that easy either... the city proper was a walled city, and the gates were maned at all times... I couldn't exactly stroll out the gates without people knowing about it. And even if I left, my brother would probably have people always hunting for me... he couldn't risk me comming back and claiming the throne. So, I sent one of my servants to contact some of my wizardly friends.
A couple days later, I met with the head of the guild in secret. He informed me that there were no wizards at the guild familiar enough with transmutation type magic (The only magic "officialy" allowed was scrying and similar, and while the wizard guild did know a little other magic, it wasn't much) to polymorph me or similar, they did have a theoretical plan, but it was sort of... extreme. Among the things the guild took care of was a repository of magic items. Well hidden through a secret passage in a cellar, there was a warded vault that contained several dozen magical items the guild had secreted away. Due to the rarity of magic in the kingdom, they took anything they could get, no matter how minor... or cursed. Somehow, for unknown reasons, they had a Girdle of Masculinity/Femininity(sp?).
I wasn't, however, that desperate. I told them to keep looking.
That very night, as I was getting ready for bed, I heard a noise in the wall... the wall I knew had a secret passage behind it that I had used when I was a kid to sneek out of my room. I quickly climbed out my window and scooted along the ledge a bit so I was out of sight. A moment later I heard movement in my room, so I peered in. I saw a cloaked man with a sword moving about, looking under the bed, in the closet, etc. An assassin.
I carefully dropped down to the next ledge below me, which led to to my servants quarters. He helped me get out of the castle quickly. I ran to the wizards guild and knocked untill someone woke up, and I explained what had hapened to my friends there. I told them, too, that pride and self-image be darned right now, I wanted to live. So we carried out their plan. I put the belt on long enough for the change to take over, then they cast a form of remove curse... not on me, though, just the belt. In retrospect, I learned, that wasn't the wisest thing to do with the way magic worked in this campagin, but...
So, for the next several months I stayed and worked as an aprentice to them, and picked up my first level of wizard. When the assorted confusion brought upon by the heirs disapearance and the kings death cleared up, I walked out of the city through the main gates. I got to another kingdom and attempted to use the gold to get the 'curse' removed. Like I said, oops. When the belt had been de-cursed, the magic that brought about the change was destroyed. I was no longer actualy under a curse per say... the new body had become my real one. Remove curse would do nothing. Naaaaaaaaar.
After ploting a half-dozen ways to kill the wizards back home, I eventualy gave up... it wasn't exactly their fault, they were just ignorant thanks to the laws of my kingdom. Not that that made me any happier, mind, but still...
And that's more or less where the campagin itself started... I was getting drunk in a bar, as was my ritual every since I learned what had happened.