Chip Esten - S7.E8

Chip appears on Let's Make a Date, hoping to choose from a mean female wrestler who receives a Valentine and is desperate to find her secret admirer (Wayne), the mad Headless Horseman looking for a hideous head to replace his own (Colin), and a mischievous gargoyle at the top of Notre Dame Cathedral who keeps coming alive to cause trouble (Ryan); ""Film, TV, and Theater Styles"" is Colin is a distraught bride, and Wayne is her angry mother, coming to fashion designer Ryan on the morning of the wedding since the dress doesn't fit, in the styles of MacGyver, soap opera, pyschic network, WWF, Crocodile Hunter, and Antique Roadshow; then a Doo-Wop about Erica, who died tragically in a freak gene-splicing accident; ""Songs of the Lunchlady"" in Greatest Hits, with hillbilly (""Aprons, Hairnets, and Knee-Highs"") and punk (""Don't Want Your Milk!"").

Colin wins, so it's Chip and Wayne vs. Ryan and Drew in Props.