
About this season
The show where everything's made up and the points don't matter. Not a talk show, not a sitcom, not a game show, Whose Line Is It Anyway? is a completely unique concept to network television. Four talented actors perform completely unrehearsed skits and games in front of a studio audience. Host Drew Carey sets the scene, with contributions from the audience, but the actors rely completely on their quick wit and improvisational skills. It's genuinely improvised, so anything can happen - and often does.
Episodes (39)

1. Chip Esten
8.0Aired 16 September 1999 • 22 min
Games played include: Let's Make A Date, Three-Headed Broadway Star, Props, Stand Sit & Lie, Greatest Hits, and Hoedown.

2. Brad Sherwood
Aired 23 September 1999 • 22 min
Games played include: Weird Newscasters, Duet, Newsflash, Party Quirks, Scenes from a Hat, and Hoedown.

3. Greg Proops
8.0Aired 30 September 1999 • 22 min
Games played include: Weird Newscasters, African Chant, Scenes from a Hat, Change Emotion, Greatest Hits, and Hoedown.

4. Greg Proops
8.0Aired 7 October 1999 • 22 min
Games played include: Let's Make A Date, Film Dub, Three-Headed Broadway Star, Film, TV & Theater Styles, Greatest Hits, and World's Worst.

5. Chip Esten
9.0Aired 7 October 1999 • 22 min
Games played include: Weird Newscasters, Duet, Scenes from a Hat, Whose Line?, Hoedown, and Questions Only.

6. Denny Siegel
9.0Aired 14 October 1999 • 22 min
Games played include: Weird Newscasters, Song Styles, Scenes from a Hat, Newsflash, Three-Headed Broadway Star, and Hoedown.

7. Brad Sherwood
7.0Aired 21 October 1999 • 22 min
Games played include: Let's Make A Date, Superheroes, Ballad Of, If You Know What I Mean, Greatest Hits, and 90 Second Alphabet.

8. Josie Lawrence
7.0Aired 28 October 1999 • 22 min
Games played include: Let's Make A Date, Film, TV & Theater Styles, Newsflash, Weird Newscasters, Duet, and Foreign Film Dub.

9. Brad Sherwood
10.0Aired 4 November 1999 • 22 min
Games played include: Song Titles, Gangsta Rap, Scenes from a Hat, Weird Newscasters, Three-Headed Broadway Star, and Hoedown.

10. Greg Proops
Aired 4 November 1999 • 22 min
Games played include: Superheroes, Song Styles, Newsflash, Questionable Impressions, Hats, and Three-Headed Broadway Star.

11. Greg Proops
8.0Aired 11 November 1999 • 22 min
Games played include: Let's Make A Date, Film, TV & Theater Styles, Props, Party Quirks, Song Styles, and World's Worst.

12. Chip Esten
8.0Aired 11 November 1999 • 22 min
Games played include: Let's Make A Date, Song Styles, Props, Party Quirks, Hoedown, and Three-Headed Broadway Star.
13. Josie Lawrence
8.0Aired 18 November 1999 • 22 min
Games played include: Questions Only, Whose Line?, Props, Scenes from a Hat, Greatest Hits, and Hoedown.

14. Brad Sherwood
8.0Aired 25 November 1999 • 22 min
Games played include: Superheroes, Film, TV & Theater Styles, Props, Motown Group, The Millionaire Show, and Hoedown.

15. Denny Siegel
7.0Aired 2 December 1999 • 22 min
Games played include: Let's Make A Date, Song Styles, Narrate, Weird Newscasters, Scene to Rap, and Hoedown.

16. Greg Proops
7.0Aired 9 December 1999 • 22 min
Games played include: Change of Cast, Song Styles, Props, Weird Newscasters, Moving People, Hoedown, and 90 Second Alphabet.

17. Brad Sherwood
7.0Aired 16 December 1999 • 22 min
Games played include: Weird Newscasters, Duet, Whose Line?, Party Quirks, Scenes from a Hat, and Hoedown.

18. Brad Sherwood
8.0Aired 6 January 2000 • 22 min
Games played include: Superheroes, Film, TV & Theater Styles, Song Titles, Sound Effects, Telethon, and Three-Headed Broadway Star.

19. Greg Proops
8.0Aired 13 January 2000 • 22 min
Games played include: Weird Newscasters, Questionable Impressions, Scenes from a Hat, Whose Line?, Three-Headed Broadway Star, Hoedown.

20. Kathy Greenwood
8.0Aired 20 January 2000 • 22 min
Games played include: Questions Only, Sound Effects, Props, Newsflash, Greatest Hits, and Foreign Film Dub.

21. Chip Esten
Aired 3 February 2000 • 22 min
Games played include: Superheroes, Film, TV & Theater Styles, Newsflash, Duet, Party Quirks, and 90 Second Alphabet.

22. Kathy Greenwood
Aired 3 February 2000 • 22 min
Games played include: Weird Newscasters, Song Styles, Themed Restaurant, Narrate, Scenes from a Hat, and Hoedown.

23. Greg Proops
Aired 10 February 2000 • 22 min
Games played include: Weird Newscasters, African Chant, Scenes from a Hat, Scene With an Audience Member, Hats, 90 Second Alphabet.

24. Chip Esten
Aired 17 February 2000 • 22 min
Games played include: Superheroes, Title Sequence, Scenes from a Hat, Narrate, Greatest Hits, and 90 Second Alphabet.

25. Greg Proops
Aired 24 February 2000 • 22 min
Games played include: Superheroes, Sound Effects, Song Styles, The Millionaire Show, and Hoedown.

26. Brad Sherwood
Aired 2 March 2000 • 22 min
Games played include: Let's Make A Date, Scene To Rap, Props, Moving People, Greatest Hits, and Questions Only.

27. Greg Proops
Aired 9 March 2000 • 22 min
Games played include Weird Newscasters, Song Styles, Sound Effects, Number of Words, Party Quirks, Scene to Rap, and Hoedown.

28. Karen Maruyama
Aired 16 March 2000 • 22 min
Games played include: Questions Only, Song Styles, Sound Effects, Newsflash, Scenes from a Hat, Motown Group, and Foreign Film Dub.

29. Greg Proops
Aired 23 March 2000 • 22 min
Games played include: Let's Make A Date, Song Styles, Party Quirks, Improbable Mission, and Three-Headed Broadway Star.

30. Brad Sherwood
Aired 30 March 2000 • 22 min
Games played include: Let's Make A Date, Film, TV & Theater Styles, Props, Newsflash, Greatest Hits, and World's Worst.

31. Denny Siegel
Aired 6 April 2000 • 22 min
Games played include: Let's Make A Date, Sound Effects, Props, Moving People, Hoedown, and Helping Hands.

32. Karen Maruyama
Aired 20 April 2000 • 22 min
Games played include: Film, TV & Theater Styles, Weird Newscasters, Song Styles, Party Quirks, The Millionaire Show, and Hoedown.

33. Chip Esten
Aired 27 April 2000 • 22 min
Games played include: Weird Newscasters, Scene to Rap, Props, Newsflash, Greatest Hits, and Questions Only.

34. Brad Sherwood
Aired 27 April 2000 • 22 min
Games played include: Let's Make A Date, Newsflash, Title Sequence, Whose Line?, Scenes from a Hat, and Hoedown.

35. Brad Sherwood
Aired 4 May 2000 • 22 min
Games played include: Weird Newscasters, Film Dub, Questionable Impressions, Narrate, Greatest Hits, and 90 Second Alphabet.

36. Chip Esten
Aired 4 May 2000 • 22 min
Games played include: Superheroes, Let's Make A Date, Duet, Whose Line?, Scenes from a Hat, and Props.

37. Brad Sherwood
Aired 11 May 2000 • 22 min
Games played include: Film, TV & Theater Styles, Film Dub, Quick Change, Motown Group, If You Know What I Mean, Greatest Hits, and Props.

38. Denny Siegel
Aired 18 May 2000 • 22 min
Games played include: Questions Only, Film, TV & Theater Styles, Scenes from a Hat, Old Job New Job, Greatest Hits, and Hoedown.

39. Chip Esten
Aired 18 May 2000 • 22 min
Games played include: Film, TV & Theater Styles, Duet, Song Titles, Newsflash, Hoedown, and Foreign Film Dub.