When the Mayor's office competes against City Council in an annual Thanksgiving contest, the stakes are high, since the losers must croon a show tune in front of the press. James has trouble breaking up with a longtime girlfriend visiting from Wisconsin.
Quest roles:
Victoria Dillard(Janelle Cooper), Ed Koch, Rudy Ruggiero(Journalist (uncredited)), J. Smith-Cameron(Lisa), Stephen Colbert(Frank), Jennifer Garner(Becky), Brian Tarantina(First Homeless Man), William Preston(Older Homeless Man), James E. Tripp(Reporter)