steeldragons
Steeliest of the dragons
While I am fine with your list for the most part Just wanted to say something about these three. On Heroes if you were going to take characters from Order of the Stick, I don't get why you chose Durkon of all characters to represent the Heroes instead of Roy or Elan. Durkon's thing was he was more boring then the rest of them.
Roy is relatively boring but I had a good amount of fighters already. Elan is downright incompetent/comic relief. He's great for a webcomic. Not so much for a "legitimate" group.
Re: Durkon, I didn't choose him to "represent" OotS. I was making a list of heroes to kick some "A." I chose him because I thought I needed another Cleric type. A bunch of the "bad guys" are undead or undead adjacent... and I was trying to stay away from just listing every character from Dragonlance (Goldmoon was the first that came to mind).
The options for clerics from D&D sources are really few and far between. What's her name...Robin whatever the Druid, from FR was the other option...but, again, I felt like I was using a ton of Forgotten Realms and wanted to spread out the OotS folks.
On Villains it's once again if you are going to pick a villain to represnet Order of the Stick why pick the relatively minor villain Tsukiko rather then main villain Xykon.
Again, see above re: "representing" anything.
I was filling out the roster. She was actually my last selection/choice. I wanted another woman. I wanted another clericy-type. She had to be evil. She had the extra benefit of being culturally/racially diverse...and setting up the 80's cartoon in my head, gave Ishi a perfect direct foil (pwhich would presumed to be from her homeland) as well as generating undead for Durkon to take on (for a direct OotS v. OotS match up).
Lastly on Anti Heroes. This is just a straight up correction. Drizzt is not an anti hero, he is just a straight up hero. He's a nicer and more noble person then most on your Heroes list like Wulfgar and Gord.
Drizzt is an overused piece of crap and he knows it. He's lucky to be on the list at all. Nice guy or not, he's a drow. So Gilthanas hates him. He's a "good drow." So Eclavdra hates him. AND, as the ranger from the snow-filled north, he's a loner...doesn't fit in anywhere...is capable as an agent of someone else, but he's not going to Mary Sue up my list of actual heroes. He's feared and despised while he does the right thing and fights the good fight...he is, by definition, an anti-hero.
Gord is conflicted, but ultimately a good guy...and literally the only thief/rogue character that's not a halfling without stepping outside of D&D characters and stealing the Grey Mouser. Wulfgar, I really don't know anything about beyond Crystal Shard...wherein he was basically a capable naive barbarian who eventually got a magic hammer made by Bruenor (or, at least, that's pretty much all I remember having not read it in multiple decades). For that, he can be on the list of warrior types and a nice unique "type" to play off of Tanis and Vajra, et al. more expert straightforward fighting styles.