Narrator (voice)
Self (as Phil Orbanes)
Self
Self (as Dave Ulmer)
Dr. Caroline 'Cathy' Ryan (archive footage)
Jack Donaghy (archive footage)
Beth (archive footage)
Howard Cunningham (archive footage)
Monopoly Woman #2 (archive footage)
Raymond 'Spike' Fonzarelli (archive footage)
Felix DeSouza (archive footage)
Bart Simpson (archive footage)
Dr. Cliff Huxtable (archive footage)
Whitney 'Cam' Cameron (archive footage)
Self (archive footage)
Martini (archive footage)
Mr. Monopoly
Elisa (archive footage)
Richie Cunningham (archive footage)
Jamie Buchman (archive footage)
Elmo McElroy (archive footage)
Monopoly Man (archive footage)
Monopoly Woman #1 (archive footage)
Self (archive footage) (as Judge Greg Mathis)
Joanie Cunningham (archive footage)
Dakota Parker (archive footage)
David Staebler (archive footage)
Harding (archive footage)
Fred Flintstone (archive footage)
Paul Buchman (archive footage)
Doug Cameron (archive footage)
Danny Donahue (archive footage)
Wheeler (archive footage)
Wilma Flintstone (voice) (archive footage)
Theo Huxtable (archive footage)
Charlie Brown (archive footage)
Chris (archive footage)