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| Episode 1 - [Kathy Greenwood] |
| Details : Games playing include: Weird Newscasters Song Styles Scenes from a Hat What Are You Trying to Say? Party Quirks and Irish Drinking Song. Winner: Kathy Greenwood. |
| Air Date : Oct. 12, 2000 |
| Episode 2 - [Chip Esten] |
| Details : Games played include: Let's Make A Date Scene with an Audience Member Sound Effects (with audience members) Motown Group and Three-Headed Broadway Star. Winner: Colin Mochrie. |
| Air Date : Oct. 12, 2000 |
| Episode 3 - [Chip Esten] |
| Details : Games played include: Hollywood Director Duet Narrate Themed Restaurant Greatest Hits and Three-Headed Broadway Star. Winner: Colin Mochrie. |
| Air Date : Oct. 19, 2000 |
| Episode 4 - [Greg Proops] |
| Details : Games played include: Weird Newscasters Sound Effects (with audience members) Song Styles Newsflash Irish Drinking Song and World's Worst. Winner: Wayne Brady. |
| Air Date : Oct. 19, 2000 |
| Episode 5 - [Greg Proops] |
| Details : Games played include: Survival Show Scenes from a Hat Reunion Greatest Hits and Props. Winner: Greg Proops. |
| Air Date : Oct. 26, 2000 |
| Episode 6 - [Brad Sherwood] |
| Details : Games played include: Let's Make A Date Duet Infomercial Scenes Cut from a Movie Irish Drinking Song and Foreign Film Dub. Winner: Colin Mochrie. |
| Air Date : Nov. 02, 2000 |
| Episode 7 - [Jeff Davis] |
| Details : Games played include: Weird Newscasters Scenes from a Hat Party Quirks Greatest Hits and Hoedown. Winner: Jeff Davis. |
| Air Date : Nov. 02, 2000 |
| Episode 8 - [Kathy Greenwood] |
| Details : Games played include: Film TV And Theater Styles Song Styles Narrate Newsflash Motown Group and Hoedown. Winner: Kathy Greenwood. |
| Air Date : Nov. 09, 2000 |
| Episode 9 - [Robin Williams] |
| Details : Games played include: Hollywood Director Duet Party Quirks Scenes from a Hat and Props. Winner: Colin Mochrie. |
| Air Date : Nov. 16, 2000 |
| Episode 10 - [Chip Esten] |
| Details : Games played include: Superheroes Duet Scenes from a Hat Whose Line? Greatest Hits and Three-Headed Broadway Star. Winner: Wayne Brady And Ryan Stiles. |
| Air Date : Nov. 23, 2000 |
| Episode 11 - [Greg Proops] |
| Details : Games played include: Let's Make A Date Multiple Personalities Hats Props Dead Bodies Scene to Rap and Stand Sit And Bend. Winners: Colin Mochrie And Ryan Stiles. |
| Air Date : Nov. 23, 2000 |
| Episode 12 - [Chip Esten] |
| Details : Games played include: Superheroes Duet Good Cop Bad Cop Sound Effects (with audience members) Irish Drinking Song and Props. Winner: Colin Mochrie. |
| Air Date : Nov. 30, 2000 |
| Episode 13 - [Greg Proops] |
| Details : Games played include: Let's Make A Date Film Dub Film TV And Theater Styles Themed Restaurant Greatest Hits and Props. Winners: Wayne Brady Colin Mochrie And Ryan Stiles. |
| Air Date : Dec. 14, 2000 |
| Episode 14 - [Greg Proops] |
| Details : Games played include: Superheroes Film TV And Theater Styles Hats Greatest Hits and World's Worst. Winner: Wayne Brady. |
| Air Date : Jan. 04, 2001 |
| Episode 15 - [Jeff Davis] |
| Details : Games played include: Let's Make A Date Whose Line? Props Sound Effects (with audience members) Duet and Hoedown. Winner: Jeff Davis. |
| Air Date : Jan. 11, 2001 |
| Episode 16 - [Chip Esten] |
| Details : Games played include: Film TV and Theatre Styles Duet Song Titles Party Quirks Greatest Hits Hoedown Winner: Wayne Brady Chip Esten Colin Mochrie And Ryan Stiles. |
| Air Date : Jan. 25, 2001 |
| Episode 17 - [Kathy Greenwood] |
| Details : Games played include: Questions Only Sound Effects Three-Headed Broadway Star Scenes Cut from a Movie The Millionaire Show and Hoedown. Winner: Kathy Greenwood. |
| Air Date : Feb. 01, 2001 |
| Episode 18 - [Brad Sherwood] |
| Details : Games played include: Weird Newscasters Award Show If You Know What I Mean Greatest Hits and Props. Winner: Colin Mochrie. |
| Air Date : Feb. 21, 2001 |
| Episode 19 - [Greg Proops] |
| Details : Games played include: Hollywood Director Song Styles Sound Effects Hats and Three-Headed Broadway Star. Winners: Greg Proops And Colin Mochrie. |
| Air Date : Feb. 21, 2001 |
| Episode 20 - [Jeff Davis] |
| Details : Games include: Questionable Impressions Film TV And Theater Styles Irish Drinking Song Duet Newsflash Hoedown and Foreign Film Dub. Winner: Wayne Brady. |
| Air Date : Feb. 22, 2001 |
| Episode 21 - [Greg Proops] |
| Details : Games played include: Weird Newscasters Two-Line Vocabulary Party Quirks Greatest Hits and Props. Winner: Greg Proops. |
| Air Date : Mar. 15, 2001 |
| Episode 22 - [Chip Esten] |
| Details : Games played include: Superheroes Sound Effects Three-Headed Broadway Star Whose Line? Irish Drinking Song and Helping Hands. Winner: Wayne Brady. |
| Air Date : Mar. 15, 2001 |
| Episode 23 - [Greg Proops] |
| Details : Games played include: Let's Make A Date Narrate Song Styles The Millionaire Show and Hoedown. Winner: Greg Proops. |
| Air Date : Mar. 22, 2001 |
| Episode 24 - [Brad Sherwood] |
| Details : Games played include: Superheroes Two-Line Vocabulary Scenes from a Hat Greatest Hits and Three-Headed Broadway Star. Winner: Colin Mochrie. |
| Air Date : Mar. 22, 2001 |
| Episode 25 - [Brad Sherwood] |
| Details : Games played include: Weird Newscasters Doo Wop Narrate Greatest Hits and Props. Winner: Wayne Brady. |
| Air Date : Mar. 29, 2001 |
| Episode 26 - [Greg Proops] |
| Details : Games played include: Sound Effects Song Styles Scenes from a Hat Improbable Mission Three-Headed Broadway Star and Props. Winner: Greg Proops. |
| Air Date : Apr. 05, 2001 |
| Episode 27 - [Kathy Greenwood] |
| Details : Games played include: Questions Only African Chant The Millionaire Show Scenes from a Hat and Hoedown. Winner: Kathy Greenwood. |
| Air Date : Apr. 12, 2001 |
| Episode 28 - [Kathy Greenwood] |
| Details : Games played include: Let's Make A Date Scene With an Audience Member Props Greatest Hits and Foreign Film Dub. Winner: Wayne Brady. |
| Air Date : Apr. 19, 2001 |
| Episode 29 - [Kathy Greenwood] |
| Details : Games played include: Film TV And Theater Styles Song Styles The Millionaire Show Motown Group and Hoedown. Winner: Kathy Greenwood. |
| Air Date : Apr. 26, 2001 |
| Episode 30 - [Brad Sherwood] |
| Details : Games played include: Hollywood Director Duet Sound Effects Three-Headed Broadway Star and Quick Change. Winner: Colin Mochrie. |
| Air Date : Apr. 27, 2001 |
| Episode 31 - [Greg Proops] |
| Details : Games played include: Superheroes Song Styles Improbable Mission Scenes from a Hat and Hoedown. Winner: Greg Proops. |
| Air Date : Apr. 27, 2001 |
| Episode 32 - [Greg Proops] |
| Details : Games played include: Superheroes Film TV And Theater Styles Wedding Greatest Hits and Three-Headed Broadway Star. Winner: Greg Proops. |
| Air Date : May. 03, 2001 |
| Episode 33 - [Chip Esten] |
| Details : Games played include: Superheroes Duet Scenes Cut from a Movie Greatest Hits and Hoedown. Winners: Wayne Brady Chip Esten Colin Mochrie And Ryan Stiles. |
| Air Date : May. 04, 2001 |
| Episode 34 - [Kathy Greenwood] |
| Details : Games played include: Let's Make A Date Film TV And Theater Styles Motown Group Party Quirks Three-Headed Broadway Star and 90 Second Alphabet. Winners: Colin Mochrie And Ryan Stiles. |
| Air Date : May. 04, 2001 |
| Episode 35 - [Kathy Greenwood] |
| Details : Games played include: Hollywood Director Infomercial Action Replay Greatest Hits and Props. Winner: Kathy Greenwood. |
| Air Date : May. 10, 2001 |
| Episode 36 - [Chip Esten] |
| Details : Games played include: Weird Newscasters Sound Effects Song Titles Film TV And Theater Styles Motown Group and Hoedown. Winner: Wayne Brady. |
| Air Date : May. 17, 2001 |
| Episode 37 - [Greg Proops] |
| Details : Games played include: Number of Words Song Styles Show Stopping Number Scenes from a Hat and Hoedown. Additional segments include: Statements That Will Be Bleeped By the Censor and Outtakes from Whose Line. Winner: Greg Proops. |
| Air Date : May. 18, 2001 |
| Episode 38 - [Kathy Greenwood] |
| Details : Games played include: Weird Newscasters Song Styles Action Replay Party Quirks and Hoedown. |
| Air Date : Jun. 14, 2001 |
| Episode 39 - [Brad Sherwood] |
| Details : Games played include: Let's Make A Date Two-Line Vocabulary Greatest Hits and World's Worst. Winner: Brad Sherwood. |
| Air Date : Jun. 21, 2001 |