The film follows several characters as they spend New Year's Eve in New York City before eventually showing up at Monica's party. The party guests are: Val (Christina Ricci) and Stephie (Gaby Hoffmann), teens from Ronkonkoma who get lost in the seedy Alphabet City section of the borough and wander into a punk club where they meet Dave (Guillermo Díaz) and Tom (Casey Affleck), who have a "package" they need to deliver; ditsy and awkward Cindy (Kate Hudson), who is on a dinner date with the paranoid Jack (Jay Mohr); Lucy (Courtney Love) and her best friend Kevin (Paul Rudd), who are struggling with the sexual tension between them; Kevin's feminist ex-girlfriend Ellie (Janeane Garofalo), who walks in on Kevin and Lucy making out in a restroom stall; a dim-witted and flirtatious bartender (Ben Affleck); competitive friends Bridget (Nicole Ari Parker) and Caitlyn (Angela Featherstone) who attempt to ditch Bridget's boyfriend Eric (Brian McCardie), (who is also Monica's ex-boyfriend); and the eccentric cab driver (Dave Chappelle) who takes them all around town throughout the evening in his disco-themed taxi.