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At some point when people started pointing out that his hair looked like shit to him, he must've stopped and thought,
"Hmm, I could afford the best of hair replacement cosmetic surgery...
but the enlightened individual cares not about perceived physical imperfections...
or I could let it stay like that and it'll attract attention, of the negative variety, but hey."
Or maybe it was more a slippery slope and things got out of control and now he's deluded himself into thinking it looks awesome.
Humorous journalism article reporting there though.