Played by: Joe Pantoliano

During his brief time on The Sopranos, Ralph Cifaretto was one of the excellent drama's most interesting characters. Ralphie earned more than his fair share of money during his mob career, but he was also incredibly violent and untrustworthy. He took care of the business side of things without any trouble; when it came to his personal life, though, Cifaretto was a trainwreck.

Between killing strippers in public and setting fire to Tony’s beloved horse purely for the insurance money, Cifaretto could never stay in the good graces of his ill-tempered boss. It was only a matter of time before the two had it out in a brutal kitchen brawl that ranks amongst the series’ highlights.

Most of the praise for the character has to go to Joe Pantoliano's performance. The veteran actor brought an intimidating sleaziness to Cifaretto that cemented his status as one of the show’s more memorable troublemakers.