Feels like a great DM could make a cautionary tale out of a character who only rolls 20s, like the creeping horror of always succeeding in the most over the top way.
Reminds me of the skill check passes in Disco Elysium that are more or less fails - like the bocci game where you chuck the ball into the ocean instead of playing like a normal person
Homebrew a cursed magic item that has negative effects on any roll of 20 and cannot be removed due to the curse
Not really, he'd probably make a Barbarian with maxed out intelligence if his Elden Ring build is any indication
Nah, he'd chuck the worst "that guy" temper tantrum imaginable. Like, it wouldn't even be funny, it would be so pathetic that you'd die from witnessing the sheer amount of cringe.
Perhaps this is what it takes to get people to Play Another Game.
I guess if he does to dnd what he did to twitter, it would make people try out some other tabletop games instead.