This Criss Angel photo contains
fedora, felt hat, homburg, stetson, trilby, boater, leghorn, panama, panama hat, sailor, skimmer, and straw hat.
There might also be
campaign hat, porkpie, porkpie hat, and snap brim hat.
This is Criss Angel on the show Craziest Moments. No.36 on the countdown for his Mindfreak episode "Chicken". I'm sure this episode of Craziest Moments is from (at the least) 2005.