"The Art of Losing" received generally positive reviews from music critics, who commented on the upbeat energy and lack of unoriginal music, while reaching number 80 on the US "Billboard" 200. Its title track was released to radio as the lead single in January 2003, and peaked at number 33 on the US Alternative Airplay chart. The album was promoted with a club tour, an appearance on "Late Show with David Letterman", and music videos for tracks "The Breakup Song" and "Beautiful Disaster".