Played by Joe Pantoliano
"All this over some whore?"
If the mafia gave out a Mr. Congeniality Award, Ralph Cifaretto would never be in contention for it. Mr. Obnoxious, however, would be his in a walk. Sarcastic, belligerent and misogynistic — even by wise guy standards — Ralph is easily Tony's least favorite business associate. Despite being a very smart man (albeit one who dropped out of school in the eleventh grade), Ralph is prone to making grossly inappropriate comments at the worst possible moment.