Season 2 Details Casts Episode Lists of Season 2 Title Season 2 Genres Comedy Reality Air Date 1999-09-16 Episode Runtime 00 Hours 22 Minutes Season Number 2 Episode Count On Season 2 39 Production Companies Hat Trick Productions, Angst Productions, Warner Bros. Television Drew Carey Self - Host Wayne Brady Self Ryan Stiles Self Colin Mochrie Self Laura Hall Self Episode 1 1999-09-16 Chip Esten... Episode 2 1999-09-23 Brad Sherwood... Episode 3 1999-09-30 Greg Proops... Episode 4 1999-10-07 Greg Proops... Episode 5 1999-10-07 Chip Esten... Episode 6 1999-10-14 Denny Siegel... Episode 7 1999-10-21 Brad Sherwood... Episode 8 1999-10-28 Josie Lawrence... Episode 9 1999-11-04 Brad Sherwood... Episode 10 1999-11-04 Greg Proops... Episode 11 1999-11-11 Greg Proops... Episode 12 1999-11-11 Chip Esten... Episode 13 1999-11-18 Josie Lawrence... Episode 14 1999-11-25 Brad Sherwood... Episode 15 1999-12-02 Denny Siegel... Episode 16 1999-12-09 Greg Proops... Episode 17 1999-12-16 Brad Sherwood... Episode 18 2000-01-06 Brad Sherwood... Episode 19 2000-01-13 Greg Proops... Episode 20 2000-01-20 Kathy Greenwood... Episode 21 2000-02-03 Chip Esten... Episode 22 2000-02-03 Kathy Greenwood... Episode 23 2000-02-10 Greg Proops... Episode 24 2000-02-17 Chip Esten... Episode 25 2000-02-24 Greg Proops... Episode 26 2000-03-02 Brad Sherwood... Episode 27 2000-03-09 Greg Proops... Episode 28 2000-03-16 Karen Maruyama... Episode 29 2000-03-23 Greg Proops... Episode 30 2000-03-30 Brad Sherwood... Episode 31 2000-04-06 Denny Siegel... Episode 32 2000-04-20 Karen Maruyama... Episode 33 2000-04-27 Chip Esten... Episode 34 2000-04-27 Brad Sherwood... Episode 35 2000-05-04 Brad Sherwood... Episode 36 2000-05-04 Chip Esten... Episode 37 2000-05-11 Brad Sherwood... Episode 38 2000-05-18 Denny Siegel... Episode 39 2000-05-18 Chip Esten...
