Jason Shaw was born into a prominent family in Chicago, his father being the CEO of Jefferies & Company, Inc., a global investment bank and securities firm. Good-looking and athletic, Shaw graduated from the University of Chicago in 1995, playing for the basketball team and earning a degree in history. He had planned to go into business. However, his college roommate, who was from South Beach, Florida, knew some people in the modeling business and told Jason that he had the looks and presence to make big money in the business. So he was able to attend a ProScout event held in Chicago and was immediately selected by the talent scouts who attended. He quickly was signed by the Wilhelmina Models agency and soon got an assignment with Abercrombie & Fitch, which is coveted among male models. That quickly lead to other jobs which paid well and garnered him media exposure. His big break came in 1998, when he was signed to be the lead spokesman for the company owned and named after its founder, Tommy Hilfiger. His life changed completely in 2000 after he met socialite and sometime model Paris Hilton, heiress to the Hilton hotel fortune. They hit it off immediately and became friends and frequent companions. That quickly escalated into a romance and in 2001, they became engaged. During that time, Hilton became a household name and Shaw got caught up in the massive media exposure. They broke up, then got back together and resumed their engagement. But in 2003, they broke up for good. However, their split was amicable and they remain on friendly terms. His contract with Hilfiger ended in 2003, and he decided to study acting. The exposure won him some television and film roles, including recurring parts on Third Watch (1999) and Charmed (1998), and he also co-starred with Hilton in The Hillz (2004). He hopes to turn his fame into a successful acting career.