5. Gillian Darmody
It's next to impossible to find a more damaged soul on Boardwalk Empire than former Atlantic City showgirl Gillian – her deceased son, Jimmy, comes in at a close second. Raped and impregnated at 13, it's understandable that Gillian grew up with a warped sense of right and wrong, but her sins are far more heinous than those of most mobsters: She committed incest with Jimmy, drowned an innocent man for her own financial gain, tipped off Gyp Rosetti to Nucky's whereabouts one night – resulting in a bomb at Babette's Supper Club that killed starlet Billie Kent – and worst of all, tried to erase her grandson Tommy's memories of his parents. Her arrest last week by her lover, Roy Phillips (who turned out to be a Pinkerton detective), while tragic, is a well-deserved comeuppance for her nefarious deeds.