The /r/chapotraphouse subreddit, a subreddit loosely based around a so-called "dirtbag left" podcast but was generally a left-wing shitposting subreddit, got quarantined by the Reddit admins in the late 2010s. At some point in 2020, the community sensed the ban hammer was going to drop and there was a hastily made lifeboat discord that was being posted around the subreddit until an alternative platform could be developed. The ban eventually came and the fraction of the community that made it to the discord waited around for a few months until chapo.chat was born, which was the initial version of this site. That version had been forked far enough away from upstream Lemmy in a way that made incidentally federation impossible, so we were our own site for a couple(?) of years. At some point the community wanted to distance itself from the 'brand' of the Chapo Trap House podcast and decided to rename itself Hexbear, named after a picture that was spammed on the subreddit shortly before the ban, which was just this picture: with the title "Check out this dope ass bear." Eventually after a lot of effort from the dev team, Hexbear was modified to once again be compatible with federation and the community voted on federating with other Lemmy servers on an allowlist basis. That's basically the the tl;dr of the site's history. Nothing major has happened since federation was finally turned on, unless you count the silly fiasco with losing our domain name briefly and we all had to revert to posting on chapo.chat and it looked like we might become Hexbear.chat.

As far as the makeup of the community, I don't think its known how much of the userbase were originally /r/chapotraphouse users and how many have joined since the Reddit ban. I would venture a guess that at least a significant plurality of the people here are probably from the subreddit and either came here directly from the lifeboat discord or were former /r/chapotraphouse posters/lurkers who eventually found Hexbear in the wild.