With his marriage failing, Vincent (James Franco) moves into a seedy Times Square hotel and, fueled by his success drawing customers to a struggling Korean bar, contemplates a tempting offer from mob capo Rudy Pipilo (Michael Rispoli). Meanwhile, Vincent and Frankie's (James Franco) brother-in law, Bobby (Chris Bauer), a Brooklyn construction foreman, eyes Vincent's new connections as a way to better his own lot.
Reluctantly agreeing to pinch-hit for a friend in a pornographic short, Candy (Maggie Gyllenhaal) ends up being intrigued by the filmmaking process. C.C. (Gary Carr) shows Lori (Emily Meade) the advantages of having a pimp, while Larry (Gbenga Akinnagbe) is unsettled by Darlene's (Dominique Fishback) interest in literature – and by Sandra Washington (Natalie Paul), a reporter. Police officers Chris Alston (Lawrence Gilliard, Jr.) and Danny Flanagan (Don Harvey) are joined by detectives Grossman (Brian Muller) and Haddix (Ralph Macchio) for a routine hooker round-up, as well as a raid of an adult porn shop whose peep shows cross the line.