"The Art of Losing" was released to US radio stations as the album's lead single on January 7, 2003. The track marked the start of an initiative from The Island Def Jam Music Group, which made radio singles available as digital downloads to coincide with their radio add-dates. Larry Mattera, the label's vice-president of new media, said it would aid them to gauge audience reactions as soon as people purchased the downloads. The single's German CD version includes "Deceiver", "When the Breeders Were Big", and a live version of "Flavor of the Weak" as extra tracks; the UK CD omits "Deceiver", and includes the other two tracks in addition to the music video for "The Art of Losing".