Dean Winters was born on July 20, 1964 in New York City. He has three younger siblings: Scott (an actor), Bradford (a poet/writer), and youngest sister, Blair (who runs a pediatric AIDS unit in a Manhattan hospital). He grew up on Long Island and spent his teenage years in Scottsdale, AZ where his father had been transferred for his job. The Winters family eventually moved back to NYC, while Dean was attending Colorado College. He graduated with honors from college. After graduating from college, Dean spent time in Europe (where he did some modeling on the side), Asia, and on the West Coast. At age 27, he moved back to New York City and bartended at various bars and clubs all over the city with his brother Scott. Scott persuaded Dean to attend acting school in order to do something with his life. Dean enjoyed acting almost immediately. It was through one of their 17 bartending gigs that they met Tom Fontana (creator of Oz) and befriended him. He eventually offered them work. Dean's previous roles then led Tom Fontana to offering him the role of cunning Ryan O'Reily on the popular HBO series "Oz."