The Iceman is the story of real-life mob hitman Richard "The Iceman" Kuklinski, who was reportedly responsible for over 200 murders. Richard Kuklinski (Michael Shannon) and his wife Deborah (Winona Ryder) appear to have a model American life, living with their three children in an idyllic suburban ranch house with a big lawn on a quiet street. But unbeknownst to Deborah and the kids, when Kuklinski goes off to work in the morning — or, on occasion, in the middle of dinner or the middle of the night — he is carrying out executions at the behest of the Gambino crime family, employing a wide variety of deadly methods (guns, knives, explosives, strangling, poisonings) that make it difficult to trace all the fatalities to a single killer. The Iceman shows the development of Kuklinski's career from the 1950s through the 1980s, chronicling his friendship with Gambino soldato Roy DeMeo (Ray Liotta), his mentorship under assassin Robert "Mister Softee" Pronge (Chris Evans), and his troubled relationship with his brother Joseph (Stephen Dorff), who, like Richard, was plagued by sociopathic tendencies all his life.