34. T.I. with the precisely-angled fitted in "Rubber Band Man."
Back in the day, there was only three ways to wear your hat. Straight, because you kept it a hundred and people could depend on you (think Ice Cube in the Raiders hat). Backwards, because you kept it funky fresh, but weren't to be trusted (like Wakko in the Animaniacs). Or you rocked your hat to the side because you were such a fucking rebel you refused to conform to society's agreed upon ways to wear a hat. But T.I. blew the lid off the whole fitted top game when he discovered a way to point his hat exactly at 8:55. And he angled it upward so didn't sit, it was perched on his dome ready to fly away at any moment like a sparrow. Of course, it never fell off T.I.'s head, he's too cool for the wind to blow his hat away. Sadly, the same wasn't true for the rest of us.