The age old question...
To bend or not to bend?
Dating back to the creation of the 59FIFTY, baseball player's started out wearing there caps flat. Artist like 50 Cent and other rappers would also keep there hat in pristine condition, refusing to bend the brim and keeping the sticker on, would show the ability to spend money on commodities in new condition. A true status symbol!
Tradition states however that bending the brim is the intended way of wearing them. When you bend the bill, the hat becomes less round and more oblong, the typical shape of a head.