First Aired: 1999
Contestants: Bruce, Steph, Paul
Theme/Costume: Ben, Jimmy, and the contestants all cross-dressed.
First Round Results: Bruce $500, Steph $100, Paul $0
Second Round Results: Bruce $700, Steph $100
Best of 10: Bruce 4, Ben 6
Ben defends: $4300
Bruce wins: $700
Executive Producer: Andrew J. Golder
Executive Producers: Al Burton, Byron Glore
Directed by: Dennis Rosenblatt
Announcer: Jimmy Kimmel
Supervising Producer: Terrence McDonnell
Coordinating Producer: Jennifer L. Ehrman
Production Designer: Jimmy Cuomo
Developed for Television by: Andrew J. Golder, Byron Glore, Donnie Brainard, Al Burton
Executive in Charge of Production: Meredith Fox