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 Credits: Randy Shropshire/Getty Images; Sonja Flemming, CBS; Kevin Mazur, Getty Images for TNT; Michael Gladis; HBO; Gabe Ginsberg, WireImage; Frazer Harrison/Getty Images; Jenny Anderson/WireImage; Paul Archuleta, FilmMagic