Played by: Michael Imperioli

As the young hot head in the Soprano family, Christopher Moltisanti’s tenure on the show was exceedingly unpredictable and violent (from shooting a baker for taking too long to serve him to pulling a gun on his boss and uncle in a jealous rage) but it was also some of the most compelling mob TV ever to hit the air. He was a man ruled by his personal demons, and because of that, he became a character of great sympathy and disgust. He could have risen through the ranks of the family if he had more patience and self-control, but he continuously got himself into bad relationships, drank too much, got hooked on drugs, and was a liability for the whole operation.

Moltisanti’s chaotic life was so engrossing because viewers could see themselves making similar mistakes if they were that young, rich, and powerful. He was incredibly flawed and human, but also incredibly fun to watch as you could never tell what he was going to do to piss Tony off next.