It was created in the spring of 2005 when high school senior Scotty Orr wore a sweatshirt proclaiming, "Ithaca is gangster" into class. Fellow senior Jon Bershad saw this and, sick of hearing all his fellow classmates talk about how excited they were to go to college and leave Hopewell in the dust, decided to instill a little home town pride in people. Bershad went home and made a t-shirt online which said simply "Hopewell is pimp, yo.".
The shirt came a week later and Bershad was prepared to wear it in the annual Mr. Hoval contest. Unfortunately, a suspension from school got him kicked out of the show. Undaunted he wore it to school the day he got back. The faculty was not really sure whether the slogan was provocative or not ("I don't get it, are you implying we have some kind of prostitution ring in the town"). So as to nip any potential problems in the bud, they told him to change immediately on the grounds that the shirt was offensive to women.
Bershad got his revenge, however. He found a new website and set up an online shop to sell the shirts. They started selling immediately and were soon banned on school grounds by the administration. This only made them sell harder, and to this day the slogan is sold on shirts, hoodies, bumper stickers, mugs, and even the occasional thong underwear.