Have you ever interacted with, or at least observed, the online OC community? There is an extremely common trend to make characters who are super special snowflakes. Often, but not always, Mary Sues. I can't (and won't) speak for
@overgeeked, obviously, but, Taliesin's characters do have a whiff of that mentality about them.
In my experience, players gravitating to non-standard options tends to be for one of three reasons:
- They've played everything under the sun and need something novel.
- The have a very specific concept in mind that cannot be realised elsewise.
- They're a poor roleplayer who uses it as a crutch to be distinct at best, and a spotlight hog at worst.
Outside of Critical Role, Taliesin's gaming has predominantly been Vampire: The Masquerade and Call of Cthulhu (to the surprise of no one), so it's definitely not the first. It's easy to look at Bolaire and attribute it to the second, but that hardly applies to the previous characters. With the exception of Caduceus, Taliesin's characters have been rather one-note; that note being "broken but well-meaning arsehole". Whilst Taliesin isn't a spotlight hog by any means, the impression I get is that he leans toward the least-standard option he can get away with precisely because he's so poor at differentiating through characterisation, while wanting his character to be unique.
Personally, I'd find Bolaire less egregious if he was a regular person unable to remove the mask because it's a cursed item granting him his Warlock powers. Though that's obviously a different character arc.