Seems like things started going to shit when he began with that "faux-hawk" hairstyle.
People don't realize that Jay is successful multimillionaire.... he can do anything and look like whatever and people still think he's cool
Living the dream...but there comes a time when a guy his age trying to maintain his youth by adopting faddish styles becomes pathetic.
When you worry that much about your hair at an age close to 40, you're bound to lose your shirt in the real world. And by the looks of it, Cutler lost his shirt in Vegas worrying about his hair.