It's sad that I know this DOBSON LORE but that OP image was from when he was at least attempting to draw himself semi-realistically. Apparently after a certain point he really went nuts drawing himself as a skinny guy with tons of beautiful hair, but I'm not sure exactly when that switch happened or if it was linked to any specific event the way the blue bear stuff was (maybe when he started posting on tumblr?).
But that said, I don't think drawing yourself uglier is necessarily great; it's just making yourself super attractive that's off-putting. Like, I'm no fan of Dobson but I think the stuff he's doing in the OP is fine when it comes to attempting a cartoon drawing of himself. It's whenever he changed up the style and made his avatar more of a pretty boy that goes too far into weird artist fantasy territory.