I spend a lot more time running games than I do playing, so this isn't an easy question to answer, as I generally cherish every opportunity I get to play. The character I had the most fun with ever was my Nobilis character Caleb Marsh, but I already wrote about him.
There was also Trove, a Vampire LARP character I only got to play a few times, but I had a lot of fun with.
If we stick with D&D characters, Nick the Pike is my highest level character, but his former henchman Boarface is actually a more interesting character. After failing a morale check, he took off on his own, and helped explore an abandoned temple to a snake god, and then went to hell, where he was killed by ghouls, and then came back to life as a plant person. I really need to get him into another game...
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