1 of 23The Sopranos
David Chase taught us to empathize with the bad guy when he created Tony Soprano, who struggled to deal with his overbearing mother while balancing his responsibilities to his family — and his other family. The series began the decade's anti-hero boom while exploring the role of violence in America. And somehow it was very, very funny. Its ending may be the most dissected in television history.
Photo By: Abbot Genser/HBO