Jackson got his hair cut in a barber shop where the pampering is old style. You can get a shave with a straight razor (which Jack will not do, as it gives him "the willies"), and a shoulder massage with one of those vibrating hand things that look like they can also polish your shoes and make a milkshake. You can also read an old Playboy and smoke a cigar while you wait. Jackson is only nine and is not allowed to smoke cigars. Jack used to smoke cigars but he gave it up. Hell, I used to smoke cigars and all I can say is that they're expensive and get you so jacked up on nicotine that it's hard to hear yourself screaming over the pounding of your own heart.
Jackson thinks putting on a hat is a funny thing to do when I want to take a picture of his new haircut: