When Stan realizes that he might never fulfill his dream of becoming a Best Man, he convinces his last single friend, Principal Lewis (Kevin Michael Richardson), to marry the school's Superintendent (guest voice Angelica Huston) and to choose him as his Best Man. Stan invites Lewis' old friend from prison to the wedding, only to discover a secret that could prevent the wedding from happening at all. Meanwhile, Roger finds the perfect pair of shorts, and an encounter with Ricky Martin (guest-voicing as himself) makes him question his self-confidence.