# Whose Line Is It Anyway? (American TV series) season 2

The second season of the American television series Whose Line Is It Anyway? premiered on ABC on September 16, 1999, and concluded on May 18, 2000.

## Cast
### Main

* Drew Carey
* Ryan Stiles
* Colin Mochrie
* Wayne Brady

### Recurring

* Brad Sherwood (eleven episodes)
* Greg Proops (ten episodes)
* Chip Esten (eight episodes)
* Denny Siegel (four episodes)
* Josie Lawrence (two episodes)
* Kathy Greenwood (two episodes)
* Karen Maruyama (two episodes)

## Episodes

The "winner(s)" of each episode – as chosen by host Drew Carey – are highlighted in italics. The winner would take his or her seat and call a sketch for Drew to perform (often with the help of the rest).
| No. overall | No. in season | Performers | Original air date | Prod. code | U.S. viewers |
| 21 | 1 | Wayne Brady, Chip Esten, Colin Mochrie, Ryan Stiles | September 16, 1999 (1999-09-16) | 209 | N/A |
| Games performed: Let's Make a Date, Three-Headed Broadway Star, Props, Stand Sit Lie Down, Greatest Hits, Hoedown ||||||
| 22 | 2 | Brad Sherwood, Wayne Brady, Colin Mochrie, Ryan Stiles | September 23, 1999 (1999-09-23) | 205 | N/A |
| Games performed: Weird Newscasters, Duet, Newsflash, Party Quirks, Scenes from a Hat, Hoedown ||||||
| 23 | 3 | Greg Proops, Wayne Brady, Colin Mochrie, Ryan Stiles | September 30, 1999 (1999-09-30) | 206 | N/A |
| Games performed: Weird Newscasters, African Chant, Scenes from a Hat, Change Emotion, Greatest Hits, Hoedown ||||||
| 24 | 4 | Greg Proops, Wayne Brady, Colin Mochrie, Ryan Stiles | October 7, 1999 (1999-10-07) | 201 | 5.3 rating |
| Games performed: Let's Make a Date, Film Dub, Three-Headed Broadway Star, Film, Theater & TV Styles, Greatest Hits, World's Worst ||||||
| 25 | 5 | Wayne Brady, Chip Esten, Colin Mochrie, Ryan Stiles | October 7, 1999 (1999-10-07) | 220 | 4.8 rating |
| Games performed: Weird Newscasters, Duet, Scenes from a Hat, Whose Line?, Hoedown, Questions Only ||||||
| 26 | 6 | Wayne Brady, Denny Siegel, Colin Mochrie, Ryan Stiles | October 14, 1999 (1999-10-14) | 203 | 4.8 rating |
| Games performed: Weird Newscasters, Song Styles, Scenes from a Hat, Newsflash, Three-Headed Broadway Star, Hoedown ||||||
| 27 | 7 | Brad Sherwood, Wayne Brady, Colin Mochrie, Ryan Stiles | October 21, 1999 (1999-10-21) | 202 | 5.8 rating |
| Games performed: Let's Make a Date, Superheroes, Ballad of, If You Know What I Mean, Greatest Hits, 90 Second Alphabet ||||||
| 28 | 8 | Wayne Brady, Josie Lawrence, Colin Mochrie, Ryan Stiles | October 28, 1999 (1999-10-28) | 212 | N/A |
| Games performed: Let's Make a Date, Film TV and Theatre Styles, Newsflash, Weird Newscasters, Duet, Foreign Film Dub ||||||
| 29 | 9 | Brad Sherwood, Wayne Brady, Colin Mochrie, Ryan Stiles | November 4, 1999 (1999-11-04) | 221 | N/A |
| Games performed: Song Titles, Gangsta Rap, Scenes from a Hat, Weird Newscasters, Three-Headed Broadway Star, Hoedown ||||||
| 30 | 10 | Greg Proops, Wayne Brady, Colin Mochrie, Ryan Stiles | November 4, 1999 (1999-11-04) | 204 | N/A |
| Games performed: Superheroes, Song Styles, Newsflash, Questionable Impressions, Dating Service Videos, Three-Headed Broadway Star ||||||
| 31 | 11 | Greg Proops, Wayne Brady, Colin Mochrie, Ryan Stiles | November 4, 1999 (1999-11-04) | 222 | N/A |
| Games performed: Let's Make a Date, Film TV and Theatre Styles, Props, Party Quirks, Song Styles, World's Worst ||||||
| 32 | 12 | Wayne Brady, Chip Esten, Colin Mochrie, Ryan Stiles | November 11, 1999 (1999-11-11) | 211 | N/A |
| Games performed: Let's Make a Date, Duet, Props, Party Quirks, Hoedown, Three-Headed Broadway Star ||||||
| 33 | 13 | Wayne Brady, Josie Lawrence, Colin Mochrie, Ryan Stiles | November 18, 1999 (1999-11-18) | 223 | N/A |
| Games performed: Questions Only, Whose Line, Props, Scenes from a Hat, Greatest Hits, Hoedown ||||||
| 34 | 14 | Brad Sherwood, Wayne Brady, Colin Mochrie, Ryan Stiles | November 25, 1999 (1999-11-25) | 213 | N/A |
| Games performed: Superheroes, Film TV and Theatre Styles, Props, Motown Group, The Millionaire Show, Hoedown ||||||
| 35 | 15 | Wayne Brady, Denny Siegel, Colin Mochrie, Ryan Stiles | December 2, 1999 (1999-12-02) | 207 | N/A |
| Games performed: Let's Make a Date, Song Styles, Narrate, Weird Newscasters, Scene to Rap, Hoedown ||||||
| 36 | 16 | Greg Proops, Wayne Brady, Colin Mochrie, Ryan Stiles | December 9, 1999 (1999-12-09) | 224 | N/A |
| Games performed: Change of Cast, Song Styles, Props, Weird Newscasters, Moving People, Hoedown, 90 Second Alphabet ||||||
| 37 | 17 | Brad Sherwood, Wayne Brady, Colin Mochrie, Ryan Stiles | December 16, 1999 (1999-12-16) | 208 | N/A |
| Games performed: Weird Newscasters, Duet, Whose Line, Party Quirks, Scenes from a Hat, Hoedown ||||||
| 38 | 18 | Brad Sherwood, Wayne Brady, Colin Mochrie, Ryan Stiles | January 6, 2000 (2000-01-06) | 225 | N/A |
| Games performed: Superheroes, Film TV and Theatre Styles, Song Titles, Sound Effects, Telethon, Three-Headed Broadway Star ||||||
| 39 | 19 | Greg Proops, Wayne Brady, Colin Mochrie, Ryan Stiles | January 13, 2000 (2000-01-13) | 210 | N/A |
| Games performed: Weird Newscasters, Questionable Impressions, Scenes from a Hat, Whose Line, Three-Headed Broadway Star, Hoedown ||||||
| 40 | 20 | Wayne Brady, Kathy Greenwood, Colin Mochrie, Ryan Stiles | January 20, 2000 (2000-01-20) | 215 | N/A |
| Games performed: Questions Only, Sound Effects, Props, Newsflash, Greatest Hits, Foreign Film Dub ||||||
| 41 | 21 | Wayne Brady, Chip Esten, Colin Mochrie, Ryan Stiles | February 3, 2000 (2000-02-03) | 226 | N/A |
| Games performed: Superheroes, Film TV and Theatre Styles, Newsflash, Duet, Party Quirks, 90 Second Alphabet ||||||
| 42 | 22 | Wayne Brady, Kathy Greenwood, Colin Mochrie, Ryan Stiles | February 3, 2000 (2000-02-03) | 227 | N/A |
| Games performed: Weird Newscasters, Song Styles, Themed Restaurant, Narrate, Scenes from a Hat, Hoedown ||||||
| 43 | 23 | Greg Proops Wayne Brady, Colin Mochrie, Ryan Stiles | February 10, 2000 (2000-02-10) | 216 | N/A |
| Games performed: Weird Newscasters, African Chant, Scenes from a Hat, Scene with an Audience Member, Dating Service Videos, 90 Second Alphabet ||||||
| 44 | 24 | Wayne Brady, Chip Esten, Colin Mochrie Ryan Stiles | February 17, 2000 (2000-02-17) | 228 | N/A |
| Games performed: Superheroes, Title Sequence, Scenes from a Hat, Narrate, Greatest Hits, 90 Second Alphabet ||||||
| 45 | 25 | Greg Proops, Wayne Brady Colin Mochrie, Ryan Stiles | February 24, 2000 (2000-02-24) | 229 | 8.1 rating |
| Games performed: Superheroes, Sound Effects, Song Styles, The Millionaire Show, Hoedown ||||||
| 46 | 26 | Brad Sherwood, Wayne Brady, Colin Mochrie, Ryan Stiles | March 2, 2000 (2000-03-02) | 230 | 8.9 rating |
| Games performed: Let's Make a Date, Scene to Rap, Props, Moving People, Greatest Hits, Questions Only ||||||
| 47 | 27 | Greg Proops, Wayne Brady, Colin Mochrie, Ryan Stiles | March 9, 2000 (2000-03-09) | 231 | 8.0 rating |
| Games performed: Weird Newscasters, Song Styles, Sound Effects, Number of Words, Party Quirks, Scene to Rap, Hoedown ||||||
| 48 | 28 | Wayne Brady, Karen Maruyama, Colin Mochrie, Ryan Stiles | March 16, 2000 (2000-03-16) | 217 | N/A |
| Games performed: Questions Only, Song Styles, Sound Effects, Newsflash, Scenes from a Hat, Motown Group, Foreign Film Dub ||||||
| 49 | 29 | Greg Proops, Wayne Brady, Colin Mochrie Ryan Stiles | March 23, 2000 (2000-03-23) | 232 | 6.9 rating |
| Games performed: Let's Make a Date, Song Styles, Party Quirks, Improbable Mission, Three-Headed Broadway Star ||||||
| 50 | 30 | Brad Sherwood, Wayne Brady, Colin Mochrie, Ryan Stiles | March 30, 2000 (2000-03-30) | 233 | N/A |
| Games performed: Let's Make a Date, Film TV and Theatre Styles, Props, Newsflash, Greatest Hits, World's Worst ||||||
| 51 | 31 | Wayne Brady, Denny Siegel, Colin Mochrie, Ryan Stiles | April 6, 2000 (2000-04-06) | 234 | N/A |
| Games performed: Let's Make a Date, Sound Effects, Props, Moving People, Hoedown, Helping Hands ||||||
| 52 | 32 | Wayne Brady, Karen Maruyama, Colin Mochrie, Ryan Stiles | April 20, 2000 (2000-04-20) | 235 | N/A |
| Games performed: Film TV and Theatre Styles, Weird Newscasters, Song Styles, Party Quirks, The Millionaire Show, Hoedown ||||||
| 53 | 33 | Wayne Brady, Chip Esten, Colin Mochrie, Ryan Stiles | April 27, 2000 (2000-04-27) | 214 | N/A |
| Games performed: Weird Newscasters, Scene to Rap, Props, Newsflash, Greatest Hits, Questions Only ||||||
| 54 | 34 | Brad Sherwood, Wayne Brady, Colin Mochrie, Ryan Stiles | April 27, 2000 (2000-04-27) | 218 | N/A |
| Games performed: Let's Make a Date, Newsflash, Title Sequence, Whose Line, Scenes from a Hat, Hoedown ||||||
| 55 | 35 | Brad Sherwood, Wayne Brady, Colin Mochrie, Ryan Stiles | May 4, 2000 (2000-05-04) | 236 | 6.7 rating |
| Games performed: Weird Newscasters, Film Dub, Questionable Impressions, Narrate, Greatest Hits, 90 Second Alphabet ||||||
| 56 | 36 | Wayne Brady, Chip Esten, Colin Mochrie, Ryan Stiles | May 4, 2000 (2000-05-04) | 219 | 8.4 rating |
| Games performed: Superheroes, Let's Make a Date, Duet, Whose Line, Scenes from a Hat, Props ||||||
| 57 | 37 | Brad Sherwood, Wayne Brady, Colin Mochrie, Ryan Stiles | May 11, 2000 (2000-05-11) | 237 | N/A |
| Games performed: Film TV and Theatre Styles, Film Dub, Quick Change, Motown Group, If You Know What I Mean, Greatest Hits, Props ||||||
| 58 | 38 | Wayne Brady, Denny Siegel, Colin Mochrie, Ryan Stiles | May 18, 2000 (2000-05-18) | 238 | N/A |
| Games performed: Questions Only, Film TV and Theatre Styles, Scenes from a Hat, Old Job-New Job, Greatest Hits, Hoedown ||||||
| 59 | 39 | Wayne Brady, Chip Esten, Colin Mochrie, Ryan Stiles | May 18, 2000 (2000-05-18) | 239 | N/A |
| Games performed: Film TV and Theatre Styles, Duet, Song Titles, Newsflash, Hoedown, Foreign Film Dub ||||||