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
At least when I make moves like that, it's specifically to flout tropes everybody takes for granted and still find a way to make it work for me. (my party needed a sentient slab of beef to take and shrug off attacks once before bc our typical 'likes CON/STR-heavy classes' guy got tied up by coursework; and running basically Beast, but made a barb was a hilarious way to subvert the 'unga bunga caveman barb' tropes.)
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.