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| Episode 1 - [Chip Esten] |
| Details : Games played include: Let's Make A Date Three-Headed Broadway Star Props Stand Sit And Lie Greatest Hits and Hoedown. Winner: Wayne Brady. |
| Air Date : Sep. 16, 1999 |
| Episode 2 - [Brad Sherwood] |
| Details : Games played include: Weird Newscasters Duet Newsflash Party Quirks Scenes from a Hat and Hoedown. Winner: Wayne Brady. |
| Air Date : Sep. 23, 1999 |
| Episode 3 - [Greg Proops] |
| Details : Games played include: Weird Newscasters African Chant Scenes from a Hat Change Emotion Greatest Hits and Hoedown. Winner: Greg Proops. |
| Air Date : Sep. 30, 1999 |
| Episode 4 - [Greg Proops] |
| Details : Games played include: Let's Make A Date Film Dub Three-Headed Broadway Star Film TV And Theater Styles Greatest Hits and World's Worst. Winner: Wayne Brady. |
| Air Date : Oct. 07, 1999 |
| Episode 5 - [Chip Esten] |
| Details : Games played include: Weird Newscasters Duet Scenes from a Hat Whose Line? Hoedown and Questions Only. Winner: Chip Esten. |
| Air Date : Oct. 07, 1999 |
| Episode 6 - [Denny Siegel] |
| Details : Games played include: Weird Newscasters Song Styles Scenes from a Hat Newsflash Three-Headed Broadway Star and Hoedown. Winner: Denny Siegel. |
| Air Date : Oct. 14, 1999 |
| Episode 7 - [Brad Sherwood] |
| Details : Games played include: Let's Make A Date Superheroes Ballad Of If You Know What I Mean Greatest Hits and 90 Second Alphabet. Winners: Colin Mochrie And Ryan Stiles. |
| Air Date : Oct. 21, 1999 |
| Episode 8 - [Josie Lawrence] |
| Details : Games played include: Let's Make A Date Film TV And Theater Styles Newsflash Weird Newscasters Duet and Foreign Film Dub. Winner: Wayne Brady. |
| Air Date : Oct. 28, 1999 |
| Episode 9 - [Brad Sherwood] |
| Details : Games played include: Song Titles Gangsta Rap Scenes from a Hat Weird Newscasters Three-Headed Broadway Star and Hoedown. Winner: Wayne Brady. |
| Air Date : Nov. 04, 1999 |
| Episode 10 - [Greg Proops] |
| Details : Games played include: Superheroes Song Styles Newsflash Questionable Impressions Hats and Three-Headed Broadway Star. Winners: Wayne Brady And Ryan Stiles. |
| Air Date : Nov. 04, 1999 |
| Episode 11 - [Greg Proops] |
| Details : Games played include: Let's Make A Date Film TV And Theater Styles Props Party Quirks Song Styles and World's Worst. Winner: Wayne Brady. |
| Air Date : Nov. 11, 1999 |
| Episode 12 - [Chip Esten] |
| Details : Games played include: Let's Make A Date Song Styles Props Party Quirks Hoedown and Three-Headed Broadway Star. Winners: Wayne Brady And Ryan Stiles. |
| Air Date : Nov. 11, 1999 |
| Episode 13 - [Josie Lawrence] |
| Details : Games played include: Questions Only Whose Line? Props Scenes from a Hat Greatest Hits and Hoedown. Winners: Josie Lawrence Colin Mochrie And Ryan Stiles. |
| Air Date : Nov. 18, 1999 |
| Episode 14 - [Brad Sherwood] |
| Details : Games played include: Superheroes Film TV And Theater Styles Props Motown Group The Millionaire Show and Hoedown. Winners: Brad Sherwood Colin Mochrie And Ryan Stiles. |
| Air Date : Nov. 25, 1999 |
| Episode 15 - [Denny Siegel] |
| Details : Games played include: Let's Make A Date Song Styles Narrate Weird Newscasters Scene to Rap and Hoedown. Winner: Denny Siegel. |
| Air Date : Dec. 02, 1999 |
| Episode 16 - [Greg Proops] |
| Details : Games played include: Change of Cast Song Styles Props Weird Newscasters Moving People Hoedown and 90 Second Alphabet. Winners: Colin Mochrie And Ryan Stiles. |
| Air Date : Dec. 09, 1999 |
| Episode 17 - [Brad Sherwood] |
| Details : Games played include: Weird Newscasters Duet Whose Line? Party Quirks Scenes from a Hat and Hoedown. Winner: Wayne Brady. |
| Air Date : Dec. 16, 1999 |
| Episode 18 - [Brad Sherwood] |
| Details : Games played include: Superheroes Film TV And Theater Styles Song Titles Sound Effects Telethon and Three-Headed Broadway Star. Winners: Wayne Brady And Ryan Stiles. |
| Air Date : Jan. 06, 2000 |
| Episode 19 - [Greg Proops] |
| Details : Games played include: Weird Newscasters Questionable Impressions Scenes from a Hat Whose Line? Three-Headed Broadway Star Hoedown. Winner: Wayne Brady. |
| Air Date : Jan. 13, 2000 |
| Episode 20 - [Kathy Greenwood] |
| Details : Games played include: Questions Only Sound Effects Props Newsflash Greatest Hits and Foreign Film Dub. Winners: Kathy Greenwood Colin Mochrie And Ryan Stiles. |
| Air Date : Jan. 20, 2000 |
| Episode 21 - [Chip Esten] |
| Details : Games played include: Superheroes Film TV And Theater Styles Newsflash Duet Party Quirks and 90 Second Alphabet. Winner: Wayne Brady. |
| Air Date : Feb. 03, 2000 |
| Episode 22 - [Kathy Greenwood] |
| Details : Games played include: Weird Newscasters Song Styles Themed Restaurant Narrate Scenes from a Hat and Hoedown. Winner: Kathy Greenwood. |
| Air Date : Feb. 03, 2000 |
| Episode 23 - [Greg Proops] |
| Details : Games played include: Weird Newscasters African Chant Scenes from a Hat Scene With an Audience Member Hats 90 Second Alphabet. Winners: Colin Mochrie And Ryan Stiles. |
| Air Date : Feb. 10, 2000 |
| Episode 24 - [Chip Esten] |
| Details : Games played include: Superheroes Title Sequence Scenes from a Hat Narrate Greatest Hits and 90 Second Alphabet. Winners: Colin Mochrie And Ryan Stiles. |
| Air Date : Feb. 17, 2000 |
| Episode 25 - [Greg Proops] |
| Details : Games played include: Superheroes Sound Effects Song Styles The Millionaire Show and Hoedown. Winner: Greg Proops. |
| Air Date : Feb. 24, 2000 |
| Episode 26 - [Brad Sherwood] |
| Details : Games played include: Let's Make A Date Scene To Rap Props Moving People Greatest Hits and Questions Only. Winner: Brad Sherwood. |
| Air Date : Mar. 02, 2000 |
| Episode 27 - [Greg Proops] |
| Details : Games played include Weird Newscasters Song Styles Sound Effects Number of Words Party Quirks Scene to Rap and Hoedown. Winner: Wayne Brady. |
| Air Date : Mar. 09, 2000 |
| Episode 28 - [Karen Maruyama] |
| Details : Games played include: Questions Only Song Styles Sound Effects Newsflash Scenes from a Hat Motown Group and Foreign Film Dub. Winners: Karen Maruyama Colin Mochrie And Ryan Stiles. |
| Air Date : Mar. 16, 2000 |
| Episode 29 - [Greg Proops] |
| Details : Games played include: Let's Make A Date Song Styles Party Quirks Improbable Mission and Three-Headed Broadway Star. Winners: Wayne Brady And Ryan Stiles. |
| Air Date : Mar. 23, 2000 |
| Episode 30 - [Brad Sherwood] |
| Details : Games played include: Let's Make A Date Film TV And Theater Styles Props Newsflash Greatest Hits and World's Worst. Winner: Wayne Brady. |
| Air Date : Mar. 30, 2000 |
| Episode 31 - [Denny Siegel] |
| Details : Games played include: Let's Make A Date Sound Effects Props Moving People Hoedown and Helping Hands. Winner: Ryan Stiles. |
| Air Date : Apr. 06, 2000 |
| Episode 32 - [Karen Maruyama] |
| Details : Games played include: Film TV And Theater Styles Weird Newscasters Song Styles Party Quirks The Millionaire Show and Hoedown. Winner: Karen Maruyama. |
| Air Date : Apr. 20, 2000 |
| Episode 33 - [Chip Esten] |
| Details : Games played include: Weird Newscasters Scene to Rap Props Newsflash Greatest Hits and Questions Only. Winners: Wayne Brady Colin Mochrie And Ryan Stiles. |
| Air Date : Apr. 27, 2000 |
| Episode 34 - [Brad Sherwood] |
| Details : Games played include: Let's Make A Date Newsflash Title Sequence Whose Line? Scenes from a Hat and Hoedown. Winner: Brad Sherwood. |
| Air Date : Apr. 27, 2000 |
| Episode 35 - [Brad Sherwood] |
| Details : Games played include: Weird Newscasters Film Dub Questionable Impressions Narrate Greatest Hits and 90 Second Alphabet. Winners: Colin Mochrie And Ryan Stiles. |
| Air Date : May. 04, 2000 |
| Episode 36 - [Chip Esten] |
| Details : Games played include: Superheroes Let's Make A Date Duet Whose Line? Scenes from a Hat and Props. Winner: Chip Esten. |
| Air Date : May. 04, 2000 |
| Episode 37 - [Brad Sherwood] |
| Details : Games played include: Film TV And Theater Styles Film Dub Quick Change Motown Group If You Know What I Mean Greatest Hits and Props. Winner: Wayne Brady. |
| Air Date : May. 11, 2000 |
| Episode 38 - [Denny Siegel] |
| Details : Games played include: Questions Only Film TV And Theater Styles Scenes from a Hat Old Job New Job Greatest Hits and Hoedown. Winner: Denny Siegel. |
| Air Date : May. 18, 2000 |
| Episode 39 - [Chip Esten] |
| Details : Games played include: Film TV And Theater Styles Duet Song Titles Newsflash Hoedown and Foreign Film Dub. Winners: Wayne Brady Colin Mochrie And Ryan Stiles. |
| Air Date : May. 18, 2000 |