In a few short years, Michael Shannon has amassed a film and TV career made up of ethically and psychologically complicated men. Currently he stars on HBO's Boardwalk Empire as Nelson Van Alden, a creepily pious Prohibition agent tasked with stopping Atlantic City's rampant bootlegging operations

It must be daunting to play Eminem's nemesis, but that was nothing compared with having a sex scene with Kim Basinger, as Shannon did in 8 Mile (2002), in which he played her ne'er-do-well boyfriend

Yes, that's Shannon in Kangaroo Jack (2003), playing the film's main villain, a thug named Frankie Lombardo who wants to kill Jerry O'Connell and Anthony Anderson

Opposite Will Smith and Martin Lawrence, Shannon played a real bad boy in Bad Boys II (2003), a white supremacist hilariously named Floyd Poteet

Shannon reprised the role he played on stage opposite Ashley Judd and Harry Connick Jr. in Tracy Letts' Bug (2006), as a mentally ill veteran who believes he's been infested with parasites

Shannon donned fatigues to play a Marine searching for 9/11 survivors in the rubble in Oliver Stone's World Trade Center (2006)

In Before the Devil Knows You're Dead (2007), Shannon plays a grieving man who demands payment after Ethan Hawke's character gets his sister's husband killed

Shannon received a surprising best supporting actor nomination for Revolutionary Road (2008), in which he played the unhinged John Givings, who speaks for the audience when he tells Frank and April Wheeler (Leonardo DiCaprio and Kate Winslet) that their marriage is doomed

In The Runaways (2010), Shannon played Kim Fowler, the snake-oil-salesman manager who would make a young Joan Jett (Kristen Stewart) and Cherie Currie (Dakota Fanning) rock stars