- Episode 1Billy Crystal / Rebecca Romijn-Stamos / Dian ThomasSep 13, 1999
- Episode 2Steve Martin / Kathy Griffin / Jiminy Glick at the EmmysSep 14, 1999
- Episode 3Eric Idle / Jamie Lee Curtis / Chad LoweSep 15, 1999
- Episode 4Tom Hanks / Stone Cold Steve Austin / Jane KrakowskiSep 16, 1999
- Episode 5Kelly Preston / Wayne BradySep 17, 1999
- Episode 6Ted Danson / Jenna Elfman / Mindy SterlingSep 20, 1999
- Episode 7French Stewart / Jeff Conwick / Emmilou Harris & Linda RonstadtSep 21, 1999
- Episode 8Janeane Garofalo / Dana Delany / the Escovedo familySep 22, 1999
- Episode 9Bruce Vilanch / Bob Saget / Kristin DavisSep 23, 1999
- Episode 10Cindy Margolis / Eugene LevySep 24, 1999
- Episode 11Thomas Gibson / Eddie Griffin / DakotaSep 27, 1999
- Episode 12Rob Lowe / Julio Iglesias Jr. / Joey GreenSep 28, 1999
- Episode 13Illeana Douglas / Michael Badalucco / Joshua BellSep 29, 1999
- Episode 14David James Elliott / Bob Zmuda / Robert PalmerSep 30, 1999
- Episode 15Dennis Miller / Catherine O'Hara / Lawrence KasdanOct 1, 1999
- Episode 16Kevin Pollak / Wolfgang Puck / Smokey RobinsonOct 4, 1999
- Episode 17Bill Maher / Betty White / Harland WilliamsOct 5, 1999
- Episode 18Chevy Chase / Meatloaf / Mena SuvariOct 6, 1999
- Episode 19Paula Poundstone / Jamie Kennedy / Tony HawkOct 7, 1999
- Episode 20Little Richard / Andrea Martin / Jessica CapshawOct 8, 1999
- Episode 21Kevin Nealon / Deborah Norville / Ron Popeil / Dave KozOct 11, 1999
- Episode 22Eric McCormack / Larry Gelbart / Kevin LeeOct 12, 1999
- Episode 23Carl Reiner / Jan Hooks / Madylin SweetenOct 13, 1999
- Episode 24Molly Shannon / Bea Arthur / Antonio Sabato Jr. / Darryl HammondOct 14, 1999
- Episode 25William H. Macy / Wendie Malick / Maria BamfordOct 15, 1999
- Episode 26Bernadette Peters / Kathy Ladman / Martin MullOct 18, 1999
- Episode 27Thomas Gibson / Rita Wilson / Tom & Dick SmothersOct 19, 1999
- Episode 28Dixie Carter / Ben Savage / Joel BauerOct 20, 1999
- Episode 29Patricia Heaton / Neil Patrick Harris / Lord Of The DanceOct 21, 1999
- Episode 30Lou Diamond Phillips / Jean Smart / Peter Boyle / Cynthia Cooper & Suzy MaconnellOct 22, 1999
- Episode 31George Wallace / Jay Mohr / Rod Steiger / Graham Haley / Vonda ShepardOct 25, 1999
- Episode 32Jane Leeves / Richard Kind / Lou BegaOct 26, 1999
- Episode 33Dolly Parton / Brad Garrett / Morris Chestnut / motocross champion Travis PastranaOct 27, 1999
- Episode 34Jennie Garth / Mick Mankind Foley / Marilu HennerOct 28, 1999
- Episode 35Elvira / Melissa Joan Hart / Ryan Stiles / Bernie BrillsteinOct 29, 1999
- Episode 36Conan O'Brien / Jamie Luner / EmmeNov 1, 1999
- Episode 37Delta Burke / Harry Shearer / USA's women's soccer teamNov 2, 1999
- Episode 38Kelli Williams / Vicki Lewis / Karen Kilgarrif / Billy BlanksNov 3, 1999
- Episode 39Jay Leno / Gillian Anderson / Taye DiggsNov 4, 1999
- Episode 40Whoopi Goldberg / Andy Kindler / Dennis Overstreet / Alan CummingNov 5, 1999
- Episode 41Steve Martin / Sarah Silverman / Brian McKnightNov 8, 1999
- Episode 42Deidre Hall / Don King / Usher / Lana Wood, Tanya Roberts, Maude Adams & Lynn Holly JohnsonNov 9, 1999
- Episode 43Paul Reiser / Mary Stuart Masterson / Dian ThomasNov 10, 1999
- Episode 44Sela Ward / Chyna & Triple H. / Playboy PlaymatesNov 11, 1999
- Episode 45Kevin Meaney / Goldie Hawn / Mike Bogey Bogelowsky / Destiny's ChildNov 12, 1999
- Episode 46Ray Romano / Joan Collins / Christopher LowellNov 15, 1999
- Episode 47Roseanne / Serena Scott Thomas / Jeremy HotzNov 16, 1999
- Episode 48Drew Barrymore / Tim Daly / Debbie PuenteNov 17, 1999
- Episode 49Steven Spielberg / Jennifer Love Hewitt / Meredith BrooksNov 18, 1999
- Episode 50Pete Rose / Doris Roberts / Kate CapshawNov 19, 1999
- Episode 51This Day In History / Kurt Russell / Bob Hochet / Doug E. Doug / RoshumbaNov 22, 1999
- Episode 52Jason Alexander / Motley Crue / Jerrod MillerNov 23, 1999
- Episode 53Don Rickles / Tonic / Joe GarnerNov 24, 1999
- Episode 54Laura Dern / Jason Biggs / Tim BurtonNov 29, 1999
- Episode 55Leonard Maltin / Sandra Bernhard / Roller Derby skatersNov 30, 1999
- Episode 56Diane Keaton / Diamond Dallas & Kimberly PageDec 1, 1999
- Episode 57Jon Lovitz / Kellie Martin / Jim SilverDec 2, 1999
- Episode 58Rosie O'Donnell / Wayne BradyDec 6, 1999
- Episode 59Nathan Lane / ChicagoDec 7, 1999
- Episode 60Jonathan Lipnicki / Ali LandryDec 8, 1999
- Episode 61Michael Bolton / Countess VaughnDec 9, 1999
- Episode 62Capt. Kathy TaylorDec 10, 1999
- Episode 63Noah Wyle / the Balancing Brothers / Angelle SeelingDec 13, 1999
- Episode 64Rob Schneider / Marla Sokoloff / Bil Dwyer / Linda EvansDec 14, 1999
- Episode 65Rob Schneider / Norm CrosbyDec 15, 1999
- Episode 66Bill NyeDec 16, 1999
- Episode 67Dennis OverstreetDec 17, 1999
- Episode 68Ed Grimley's Favorite MomentsJan 3, 2000
- Episode 69Tim Allen, Artie LangeJan 4, 2000
- Episode 70Michael Clarke Duncan, Paula PoundstoneJan 5, 2000
- Episode 71Bo Derek, Enrico Colantoni, Mindy SterlingJan 6, 2000
- Episode 72Joe Flaherty, George Shapiro, Tara LipinskiJan 7, 2000
- Episode 73Uri GellerJan 10, 2000
- Episode 74Dennis Franz, Eddie Cibrian, Frankie MunizJan 11, 2000
- Episode 75Big Bad Voodoo DaddyJan 12, 2000
- Episode 76Dick Clark, Dwayne "The Rock" Johnson, Penn & TellerJan 13, 2000
- Episode 77Eric Close, Lou BegaJan 14, 2000
- Episode 78Dave Thomas, Penelope Ann Miller, Samm LevineJan 17, 2000
- Episode 79Doug Hutchison, Adam Carolla, Jimmy KimmelJan 18, 2000
- Episode 80French Stewart, Charles Nelson ReillyJan 19, 2000
- Episode 81Kimberly Williams, Caroline Rhea, Sixpence None The Richer Jan 20, 2000
- Episode 82Rick Fox, Janet McTeerJan 21, 2000
- Episode 83Sarah Ferguson, Lolita DavidovichJan 25, 2000
- Episode 84Lorraine Bracco, Robert KleinJan 26, 2000
- Episode 85Henry WinklerJan 27, 2000
- Episode 86David BrennerJan 28, 2000
- Episode 87Kathy IrelandJan 31, 2000
- Episode 88Tony Curtis, Teri GarrFeb 1, 2000
- Episode 89Vivica Fox, Danny Rapist MastersonFeb 2, 2000
- Episode 90Jenny McCarthyFeb 3, 2000
- Episode 91Diahann Carroll, Jarod Miller, Samm LevineFeb 4, 2000
- Episode 92Kathy Najimy, Jeff Dunham, Michael MichelleFeb 7, 2000
- Episode 93Paul ShafferFeb 8, 2000
- Episode 94Taylor Dayne, Jaclyn Smith, George LopezFeb 9, 2000
- Episode 95Jerry Lewis, Julia SweeneyFeb 10, 2000
- Episode 96Chevy Chase, Frances Fisher, Chubby CheckerFeb 11, 2000
- Episode 97Dwayne "The Rock" Johnson, Carol Alt, Big Bad Voodoo DaddyFeb 14, 2000
- Episode 98Richard BelzerFeb 15, 2000
- Episode 99Robert Townsend, Kareem Abdul-JabbarFeb 16, 2000
- Episode 100Diane Keaton, Peter BoyleFeb 17, 2000
- Episode 101Arianna HuffingtonFeb 18, 2000
- Episode 102Jerry Springer, Richard RoeperFeb 21, 2000
- Episode 103Leeza Gibbons, Joe QueenanFeb 22, 2000
- Episode 104Bill Maher, Bai LingFeb 23, 2000
- Episode 105Camryn Manheim, Natasha HenstridgeFeb 24, 2000
- Episode 106Dennis Miller, Marg HelgenbergerFeb 25, 2000
- Episode 107Caprice, Doug BensonFeb 28, 2000
- Episode 108John LarroquetteFeb 29, 2000
- Episode 109Sally Field, Bruno CamposMar 1, 2000
- Episode 110Ricki Lake, Wolfgang PuckMar 2, 2000
- Episode 111Forest Whitaker, Nora Dunn, Pete SamprasMar 3, 2000
- Episode 112Rob ReinerMar 6, 2000
- Episode 113Robert KleinMar 7, 2000
- Episode 114Steve Allen, Judy TenutaMar 8, 2000
- Episode 115Phyllis Diller, David ProvalMar 9, 2000
- Episode 116George Segal, Kerr Smith, Michael McDonald, Wolfgang PuckMar 10, 2000
- Episode 117Sherilyn Fenn, Geraldine FerraroMar 13, 2000
- Episode 118Marilu Henner, Ian GomezMar 14, 2000
- Episode 119Sheryl Lee Ralph, Kenny LogginsMar 15, 2000
- Episode 120George Wallace, Bob NelsonMar 16, 2000
- Episode 121Christopher TitusMar 17, 2000
- Episode 122Joan Collins, Alex BorsteinMar 20, 2000
- Episode 123Colin Mochrie, Paula PoundstoneMar 21, 2000
- Episode 124Mel Brooks, Jerry O'Connell, Laura San GiacomoMar 22, 2000
- Episode 125Jennifer Tilly, Stacy Keach, Sean Hayes, Maria Conchita AlonsoMar 23, 2000
- Episode 126SCTV reunion: Eugene Levy, Andrea Martin, Dave ThomasMar 24, 2000
- Episode 127Richard Dean Anderson, Alfred MolinaMar 27, 2000
- Episode 128George Hamilton, Sea World animalsMar 28, 2000
- Episode 129Phyllis Diller, Michael Chiklis, Leelee SobieskiMar 29, 2000
- Episode 130Kareem Abdul-Jabbar, Norm MacdonaldMar 30, 2000
- Episode 131Wendie Malick, Kathy GriffinMar 31, 2000
- Episode 132Mark Harmon, Todd GlassApr 3, 2000
- Episode 133Michael McKean, Annette O'Toole, Dave ThomasApr 4, 2000
- Episode 134Maya Angelou, Michael FeinsteinApr 5, 2000
- Episode 135David Duchovny, Rita Rudner, Colin HanksApr 6, 2000
- Episode 136Rosie O'Donnell, Jerry Springer, Deidre HallApr 7, 2000
- Episode 137Mary Steenburgen, Kate HudsonApr 10, 2000
- Episode 138Robert Loggia, Greg ProopsApr 11, 2000
- Episode 139Betty White, Ingo Rademacher, Wolfgang PuckApr 12, 2000
- Episode 140Nathan Lane, Bernadette Peters, Jason AlexanderApr 13, 2000
- Episode 141Compilation: Thomas Gibson, Ted Danson, Eric McCormackApr 27, 2000
- Episode 142Compilation: Sally Field, Diane Keaton, Rod Steiger, Isaac HayesApr 28, 2000
- Episode 143Compilation: Tom Hanks, Kurt Russell, Rob LoweMay 1, 2000
- Episode 144Compilation: Paul Reiser, Roseanne, Richard BelzerMay 2, 2000
- Episode 145Stone Cold Steve Austin, The Rock, MankindMay 3, 2000
- Episode 146Compilation: Sela Ward, Camryn ManheimMay 4, 2000
- Episode 147Compilation: Noah Wyle, Gillian Anderson, Dennis Franz, Kelli WilliamsMay 5, 2000
- Episode 148Compilation: Rosie O'Donnell, Wayne BradyMay 9, 2000
- Episode 149Compilation: Rosie O'Donnell, Wayne BradyMay 9, 2000
- Episode 150Compilation: Casper Van Dien, Debbie PuenteMay 10, 2000