Who was your first character to go from 1st level to the highest possible level in a given edition/What’s the highest level character you’ve ever run?
This is another question that’s profoundly affected by my mostly playing DnD as either a DM or in a PbP capacity. I’ve started lots, I mean lots, of characters. In college I was probably rolling up characters for between three and eight games a month. That was even more dramatic once 4e rolled around, because getting into PbP on the ground floor meant that we burned through a huge chunk of the available permutations in a few months. New books would drop, folks would descend on them like locusts, and then we’d all be crawling over each other, buzzing, waiting for the next thing. Luckily, one good quality in PbPs is the speed with which you can get a higher-level campaign up and running; this helps alleviate one bad quality of PbPs, which is that they tend to take forever to advance. I’ve rolled more characters than I’ve leveled by a factor of 20, if not more. That’s true even if the game adopts some fairly generous advancement-speeding policies.
As an example, in researching the answer to this question I cracked open my Myth-Weavers character sheet list and looked at how high one of my longest-running characters made it. He was in an incredible Deadwood-themed 4e Pathfinder game set in the River Kingdoms, and he accidentally came out as a sort of pastiche of Wu from Deadwood, but with a weird Matrix vibe to the whole thing. I loved playing him, that campaign ran for months, started at level one…and according to the sheet when we finished he was halfway to level six. That means that in terms of raw leveling, Blordik Fechual, Dragonslayer, is my highest-leveled character at a whopping eight.
However, there were plenty of Paragon-level 4th games, and mid-teens or low-twenties 3.x games. At one point in the old days, on the Pits of Evil, some friends and I ran a game where we built up low-level gods; my character, Hamelin, was built from a pair of custom basic classes, into a custom PrC, into a custom Epic class. He never actually showed up in the game, which I think was played at around level 32; he did all of his interacting through one of his four animal companions, a giant dire rat built like a golden-masked gazelle with a bladed tail who had a handful of druid levels and thus, through wild shape, appeared as a charming and erudite elf. That level of ridiculousness is why I don’t much hunger for epic games! It was fun as a collaborative fiction exercise, but we never finished posturing with our respective badasses and got to actually rolling dice for any purpose related to an actual threat. The flipside can also be a thing; I rolled a 21st level character to sub into a 4e Epic game, and we never finished the one fight that I entered into. Game ground to a halt after like a month.
High level characters: not my thing!