This is the first of two Justin Timberlake clips on our list, but they're both from the same Christmas episode in in 2006. In this one, Timberlake is dressed as a Cup-O-Soup who dances and sings to raise money for a fictional charity called "Homelessville." He is in competition for a street corner with Chris Parnell, who is dressed as Santa Claus. "Did someone say those in need" of a good laugh? Watch this one for a holiday-spirited chuckle.