It's been a slow recovery for Winona Ryder since her 2001 shoplifting scandal from Saks Fifth Avenue. In the wake of Mr. Deeds, Ryder made barely there appearances in Simone, The Informers and Black Swan, with forgettable starring roles in A Scanner Darkly, Sex and Death 101 and The Dilemma. What it all points to is that either Ryder has reached that Hollywood limbo age between old and young or her agent started to care less about her after the shoplifting scandal. Either way, the roles she has selected have been missing the inherent charm of past characters that made her iconic (e.g. Heathers, Beetlejuice and Edward Scissorhands). In Ariel Vromen's The Iceman, Ryder's role as Deborah, the clueless wife of mafia hitman Richard Kuklinski (Michael Shannon), does not allow her to shine as she should (especially sporting that faux New Jersey accent). http://youtu.be/CJIXOx2-GZ8
Based on the events of notorious contract killer Richard Kuklinski, The Iceman toes a delicate balance between humanizing the serial killer and examining his psychosis. Beginning in 1964 in Jersey City, we are introduced to Kuklinski as he goes on his first date with Deborah. Telling her that he dubs Disney movies, we soon learn what he means by "Disney" is porn. The film then transitions to 1965, by which time Kuklinski has married Deborah and had his first daughter, Betsy (Megan Sherrill). He's moved up in the world since being recruited by Roy DeMeo (Ray Liotta, always at his best as a gangster), a prominent member of the Gambino crime family. Once DeMeo closed down the porn operation, he saw in Kuklinski the opportunity to take him on as a metaphorical garbage man: Purging unwanted mafioso trash.
With their second child, Anabel (McKaley Miller), growing up fast, Kuklinski feels the pressure to make even more money so he can get his family the very best. His mania for killing becomes more intense as the heat on DeMeo gets turned up in the wake of finding out that one of his own henchmen, Josh Rosenthal (David Schwimmer, in one of his sleaziest roles to date), has been stealing both money and cocaine during every drug exchange. DeMeo finds out that a pornographic photographer named Marty Freeman (James Franco, in a strangely brief part) was the one who ratted on Rosenthal. Sending Kuklinski to take Freeman out, Kuklinski ends up letting the subject of Freeman's photography, a 17-year-old girl, go. It is at this point that another hitman, Mr. Freezy (Chris Evans, who looks vaguely like Ryan Gosling with his 70s aesthetic)--called such because he drives around in an ice cream truck--appears onto the scene. When Kuklinski finds out that he's also been hired for the same hit, his suspicions about the safety of his job are confirmed.
Upon finding out that Kuklinski failed to take out the witness to Freeman's murder, DeMeo puts him on hiatus until everything with the rival crime families are resolved. Although lending Kuklinski a touch of humanity as he explains to DeMeo that he doesn't kill women or children, his one soft spot ultimately becomes his undoing. Forced to innovate his own methods for making money while his career has been frozen (Iceman, get it?), Kuklinski partners with Mr. Freezy, who is in need of some help dismembering any number of bodies for different purposes and for different people. As alliances shift and Kuklinski begins to get more avaricious about making money, his fate is sealed for doom.
In the end, the very people Kuklinski killed for--his family--never speak to him again. Though, of course, he was probably going to kill anyway considering he had the depraved makeup of a serial killer's mind, but still. While The Iceman is engaging overall, there seems to be some component missing to make it a truly standout film. I suppose, when it comes to movies about serial killers, it's difficult to usurp Zodiac and Monster in terms of exploring motivation and psychosis.