On an icy lake, Ray Pelletier scouts out a good ice fishing spot for his family. He spots something bloody on the ice near a hole, walks toward it and falls through when the ice breaks. Back at the cabin, his wife Helen, son David and his son's girlfriend Gina are waiting for him. Ray has been struggling for hours to get out of the hole. Helen asks David and Gina what their plans are after college, and they mention that they will be joining the Peace Corps and going to Uganda following graduation.
Indifferent even to the prospects of inheriting his father’s estate, Swanson (Heidecker) whittles away his days with a group of aging Williamsburg hipsters, engaging in acts of recreational cruelty and pacified boredom. Desensitized and disenchanted, he strays into a series of reckless situations that may offer the promise of redemption or the threat of retribution.
Claire (Sara Paxton) and Luke (Pat Healy) are two young employees at the Yankee Pedlar Inn, a once-grand hotel that is about to close. Claire and Luke are the only employees working during its final weekend of operation. Claire, who suffers from severe asthma, has recently dropped out of college, and Luke runs a website chronicling the hotel's supposed hauntings. Both are ghost hunting enthusiasts and are fascinated by the hotel's supposedly haunted history, which includes the legend of Madeline O'Malley, a bride who hung herself in the 1800s when her husband abandoned her on their honeymoon, and whose body was supposedly hidden in the basement by the hotel owners.
Peter Grey is a successful New York chef, disgruntled by caustic reviews from the food critic J.T. Franks. After Franks' bad review, Grey is fired by his boss Gordon. He kidnaps Franks, takes him to a cabin in the woods, and forces him to cook his own "perfect dinner".
After her landlady (Dee Wallace) gives her an extension on the deposit for her new apartment, college student Samantha Hughes (Jocelin Donahue) takes on a babysitting job for Mr. Ulman (Tom Noonan) and his wife (Mary Woronov). Ulman asks to meet her but stands her up, later apologizing and offering to pay double the original salary. Samantha accepts and gets a ride to the remote mansion from her best friend, Megan (Greta Gerwig), who expresses her distrust. At the house, Mr. Ulman pulls her aside and reveals that he does not have any children; the babysitting job is to attend to his wife's ailing mother. Samantha balks but finally agrees, if he will pay her $400, a significant increase in her pay. Megan immediately leaves, citing Ulman's lies and peculiar behavior, but she reluctantly promises to pick up Samantha later. Samantha stays, after accepting the money. On the way home, Megan stops in her car to smoke a cigarette. When her car lighter will not work, a stranger (A.J. Bowen) suddenly appears out of nowhere, startling her, and lights her cigarette for her. When Megan reveals that she is not the babysitter hired by the Ulmans, she is abruptly shot and murdered by the stranger.
While awaiting his execution for murder and grave robbery, Arthur Blake (Dominic Monaghan) is visited by Father Duffy (Ron Perlman), who wishes to obtain a statement from the condemned to be used as a cautionary tale. Arthur denies that he is a murderer, a crime for which his former partner, Willie Grimes (Larry Fessenden), has already been executed by guillotine. However, Blake freely admits to being a grave robber, and begins to recount his career with Willie.
In an infomercial, Mickey Hauser, a spokesperson for Clara Clean Corporation, advertises Claractix, a cleaning product. Ben Richards attempts to finish a portrait of man in a suit, but he can not visualize the face, which remains blank. After several attempts, he gives up and shaves off his beard. When he meets with his coworkers, radio and newspaper reports reveal that Hauser has died and that Clara Clean Corporation has become involved in an ecological scandal. Richards and his coworkers have been recruited to come up with an ecologically-themed advertising campaign to counter this scandal, but Doug Quaid rejects all of John Kimble's stock photography. Ben suggests that they go to a Delaware campsite to seek inspiration and take their own photographs. Meanwhile, Sonia Roja's boss tells her that her boyfriend, Kimble, has one week to come up with a fantastic advertising campaign. Unless it is fantastic, Roja will take the fall. Quaid, too, feverishly repeats that the campaign must be fantastic.
Sam is a self-destructive, vaguely artistic New York bohemian who has recently lost his father and his long-time girlfriend. At a Halloween party he meets a mysterious, beautiful, androgynous woman named Anna. He embarks on a kinky, sex-charged relationship with her; but soon he suffers from a mysterious illness, and eventually comes to believe that Anna is a vampire.