| No. | Original release date | Guest(s) | Musical/entertainment guest(s) |
|---|
| 986 | September 15, 1998 (1998-09-15) | Rob Schneider, Maria Bello | Nick DiPaolo |
|---|
| 987 | September 16, 1998 (1998-09-16) | Ben Stiller, Famke Janssen | Junior Brown |
|---|
| 988 | September 17, 1998 (1998-09-17) | Caroline Rhea, Kris Kristofferson | Jud Hale |
|---|
| 989 | September 18, 1998 (1998-09-18) | Jason Priestley, George Hamilton | Los Super Seven |
|---|
| 990 | September 22, 1998 (1998-09-22) | Will Ferrell, Ken Olin | Bonnie Raitt |
|---|
| 991 | September 23, 1998 (1998-09-23) | Martin Sheen, Alicia Witt | Local H |
|---|
| 992 | September 24, 1998 (1998-09-24) | Denis Leary, Judge Judy | Jimeoin |
|---|
| 993 | September 25, 1998 (1998-09-25) | Janeane Garofalo, John Waters, PJ O'Rourke | N/A |
|---|
| 994 | September 29, 1998 (1998-09-29) | Fran Drescher, D. L. Hughley | N/A |
|---|
| 995 | September 30, 1998 (1998-09-30) | Stanley Tucci, Nicholas Turturro | Billy Bragg & Wilco |
|---|
| 996 | October 1, 1998 (1998-10-01) | Kelsey Grammer, Toni Collette, Chaz Bono | N/A |
|---|
| 997 | October 2, 1998 (1998-10-02) | Gina Gershon, Dylan McDermott | Squirrel Nut Zippers |
|---|
| 998 | October 6, 1998 (1998-10-06) | Yasmine Bleeth, Kevin Sorbo | Duncan Sheik |
|---|
| 999 | October 7, 1998 (1998-10-07) | Charlton Heston, Peter Gallagher, Rich Hall | N/A |
|---|
| 1000 | October 8, 1998 (1998-10-08) | Jeff Goldblum, Star Jones | Barenaked Ladies |
|---|
| 1001 | October 9, 1998 (1998-10-09) | Jon Stewart, Louis C.K., Annabella Sciorra | N/A |
|---|
| 1002 | October 13, 1998 (1998-10-13) | Stephen Baldwin, Jeri Ryan, Mark Leyner | N/A |
|---|
| 1003 | October 14, 1998 (1998-10-14) | Sandra Bullock, Scott Thompson | Rasputina |
|---|
| 1004 | October 15, 1998 (1998-10-15) | Lucy Lawless, Tate Donovan | Kenny Rogerson |
|---|
| 1005 | October 16, 1998 (1998-10-16) | Isabella Rossellini, David Arquette | Cake |
|---|
| 1006 | October 27, 1998 (1998-10-27) | Jeff Daniels, Christina Applegate | Robert Schimmel |
|---|
| 1007 | October 28, 1998 (1998-10-28) | Sam Donaldson, Bob Odenkirk | Mötley Crüe |
|---|
| 1008 | October 29, 1998 (1998-10-29) | Ray Romano, Reese Witherspoon, Trey Parker | Dan Naturman |
|---|
| 1009 | October 30, 1998 (1998-10-30) | Martin Short, Jimmy Blaylock | Cheap Trick |
|---|
| 1010 | November 4, 1998 (1998-11-04) | Kiefer Sutherland, Debbie Matenopoulos | Everlast |
|---|
| 1011 | November 5, 1998 (1998-11-05) | Adam Sandler, Jonathan Taylor Thomas, Frank Pellegrino | N/A |
|---|
| 1012 | November 6, 1998 (1998-11-06) | David Spade, Fred Savage | Canibus |
|---|
| 1013 | November 10, 1998 (1998-11-10) | Chris Kattan, Kate Mulgrew | Gomez |
|---|
| 1014 | November 11, 1998 (1998-11-11) | Luke Perry, Ice Cube | N/A |
|---|
| 1015 | November 12, 1998 (1998-11-12) | Richard Dean Anderson, Tom Everett Scott, Missy Giove | N/A |
|---|
| 1016 | November 13, 1998 (1998-11-13) | Roma Downey, Todd Solondz | Al Green |
|---|
| 1017 | November 17, 1998 (1998-11-17) | Kevin Pollak, Alyssa Milano | R.E.M. |
|---|
| 1018 | November 18, 1998 (1998-11-18) | Rob Schneider, Jerry Stiller, Drew Pinsky | N/A |
|---|
| 1019 | November 19, 1998 (1998-11-19) | Jennifer Love Hewitt, Marc Maron | Kevin Brennan |
|---|
| 1020 | November 20, 1998 (1998-11-20) | Charlize Theron, Jerry Springer | Everclear |
|---|
| 1021 | November 24, 1998 (1998-11-24) | Dave Foley, Garth Brooks | N/A |
|---|
| 1022 | November 25, 1998 (1998-11-25) | Jon Lovitz, Larry King, Stuttering John | N/A |
|---|
| 1023 | November 26, 1998 (1998-11-26) | Scott Thompson, Joshua Jackson | N/A |
|---|
| 1024 | November 27, 1998 (1998-11-27) | Judi Dench, Wayne Gretzky | Elvis Costello & Burt Bacharach |
|---|
| 1025 | December 8, 1998 (1998-12-08) | Senator Bob Dole, Annie Potts | Guster |
|---|
| 1026 | December 9, 1998 (1998-12-09) | Michael Moore, Rich Hall, Michael Jackson | N/A |
|---|
| 1027 | December 10, 1998 (1998-12-10) | Tom Hanks, Roger Daltrey | N/A |
|---|
| 1028 | December 11, 1998 (1998-12-11) | Alec Baldwin, Jordana Brewster | Trans-Siberian Orchestra |
|---|
| 1029 | December 15, 1998 (1998-12-15) | Robin Williams, Rebecca Romijn-Stamos, | N/A |
|---|
| 1030 | December 16, 1998 (1998-12-16) | Salma Hayek, Roberto Benigni | Shemekia Copeland |
|---|
| 1031 | December 17, 1998 (1998-12-17) | Bill Paxton, Elijah Wood | Lewis Black |
|---|
| 1032 | December 18, 1998 (1998-12-18) | Jeff Goldblum, Carol Leifer | The Flys |
|---|
| 1033 | December 22, 1998 (1998-12-22) | Tom Brokaw, Caroline Rhea | Tony Bennett |
|---|
| 1034 | December 23, 1998 (1998-12-23) | Barney Frank, Wanda Sykes | N/A |
|---|
| 1035 | December 29, 1998 (1998-12-29) | George Wendt, Camryn Manheim | Limp Bizkit |
|---|
| 1036 | December 30, 1998 (1998-12-30) | Charles Grodin | Ozomatli |
|---|
| 1037 | December 31, 1998 (1998-12-31) | James Woods, Brian Kiley | Wayne Newton |
|---|
| 1038 | January 5, 1999 (1999-01-05) | Chazz Palminteri, Anthony Clark | Irma Thomas |
|---|
| 1039 | January 6, 1999 (1999-01-06) | Al Roker, George Brett | N/A |
|---|
| 1040 | January 7, 1999 (1999-01-07) | Will Ferrell, Melina Kanakaredes | Todd Barry |
|---|
| 1041 | January 8, 1999 (1999-01-08) | Lisa Kudrow, Maury Povich | Vic Chesnutt with Lambchop |
|---|
| 1042 | January 12, 1999 (1999-01-12) | Michael Caine, Alan Cumming | G. E. Smith and Taylor Barton |
|---|
| 1043 | January 13, 1999 (1999-01-13) | Jesse Jackson, Freddie Prinze, Jr. | Arj Barker |
|---|
| 1044 | January 14, 1999 (1999-01-14) | Mira Sorvino, Greg Germann | Goo Goo Dolls |
|---|
| 1045 | January 15, 1999 (1999-01-15) | James Van Der Beek, Kevin Pollak, Roshumba Williams | N/A |
|---|
| 1046 | January 19, 1999 (1999-01-19) | Rudy Giuliani, Ryan Phillippe | Jewel |
|---|
| 1047 | January 20, 1999 (1999-01-20) | Tony Curtis, Matthew Lillard | Patti Smith |
|---|
| 1048 | January 21, 1999 (1999-01-21) | Tyra Banks, David Alan Grier | Sklar Brothers |
|---|
| 1049 | January 22, 1999 (1999-01-22) | Carmen Electra, James Coburn | Fear of Pop |
|---|
| 1050 | February 2, 1999 (1999-02-02) | Steven Wright, Kellie Martin | Marvelous 3 |
|---|
| 1051 | February 3, 1999 (1999-02-03) | Julia Sweeney, Eric McCormack | Marc Maron |
|---|
| 1052 | February 4, 1999 (1999-02-04) | Gwyneth Paltrow, Tim Russert, Jason Schwartzman | N/A |
|---|
| 1053 | February 5, 1999 (1999-02-05) | Pamela Anderson, Michael T. Weiss | Ricky Scaggs |
|---|
| 1054 | February 9, 1999 (1999-02-09) | Stephen King, Gloria Reuben | Sixpence None the Richer |
|---|
| 1055 | February 10, 1999 (1999-02-10) | John Tesh, Clyde Peeling, Jeri Ryan | N/A |
|---|
| 1056 | February 11, 1999 (1999-02-11) | Rosie O'Donnell, Daniel Stern | Patton Oswalt |
|---|
| 1057 | February 12, 1999 (1999-02-12) | Bill Maher, Fabio Lanzoni | Orgy |
|---|
| 1058 | February 16, 1999 (1999-02-16) | Dave Chappelle, Rebecca Gayheart, James Ellroy | N/A |
|---|
| 1059 | February 17, 1999 (1999-02-17) | Rosie Perez, Joshua Jackson | John Pizzarelli |
|---|
| 1060 | February 18, 1999 (1999-02-18) | Andy García, Jimmy Fallon | The Afghan Whigs |
|---|
| 1061 | February 19, 1999 (1999-02-19) | Andie MacDowell, Tony V., Myles Berkowitz | N/A |
|---|
| 1062 | February 23, 1999 (1999-02-23) | Kevin Nealon, Ed Byrne, Michael Michele | N/A |
|---|
| 1063 | February 24, 1999 (1999-02-24) | Fred Savage, Garry Marshall, Shannon Hall | N/A |
|---|
| 1064 | February 25, 1999 (1999-02-25) | Martin Short, Sarah O'Hare | The Black Crowes |
|---|
| 1065 | February 26, 1999 (1999-02-26) | Bill Murray, Jon Stewart | Natalie Merchant, Bruce Springsteen |
|---|
| 1066 | March 2, 1999 (1999-03-02) | Al Franken, Jane Krakowski | Louis C.K. |
|---|
| 1067 | March 3, 1999 (1999-03-03) | Ian McKellen, Juliette Lewis | Bare Jr. |
|---|
| 1068 | March 4, 1999 (1999-03-04) | Mark Wahlberg, Wendie Malick | N/A |
|---|
| 1069 | March 5, 1999 (1999-03-05) | Treat Williams, Penn & Teller | Crackpipe Wisconsin |
|---|
| 1070 | March 16, 1999 (1999-03-16) | John Lithgow, Darrell Hammond | Robert Schimmel |
|---|
| 1071 | March 17, 1999 (1999-03-17) | Regis Philbin, Thomas Gibson | The Chieftains |
|---|
| 1072 | March 18, 1999 (1999-03-18) | Barbara Walters, Jenna Elfman, Jerry Bivona | N/A |
|---|
| 1073 | March 19, 1999 (1999-03-19) | Claire Danes, Chris Eigeman | Steve Earle & the Del McCoury Band |
|---|
| 1074 | March 23, 1999 (1999-03-23) | Dave Foley, Jennifer Grey | N/A |
|---|
| 1075 | March 24, 1999 (1999-03-24) | Caroline Rhea, Mills Lane | N/A |
|---|
| 1076 | March 25, 1999 (1999-03-25) | Steve Austin, Louie Anderson, Ben Savage | N/A |
|---|
| 1077 | March 26, 1999 (1999-03-26) | Norm Macdonald, Roshumba Williams | Placebo |
|---|
| 1078 | March 30, 1999 (1999-03-30) | Tom Brokaw, Colin Quinn | The Neville Brothers |
|---|
| 1079 | March 31, 1999 (1999-03-31) | Thane Maynard, Dweezil & Ahmet Zappa | Greg Behrendt |
|---|
| 1080 | April 1, 1999 (1999-04-01) | Jackie Chan, Diane Lane | Al Kooper |
|---|
| 1081 | April 2, 1999 (1999-04-02) | Kevin Pollak, Josh Charles | Collective Soul |
|---|
| 1082 | April 6, 1999 (1999-04-06) | Lyle Lovett, David Brenner, Amy Sedaris | N/A |
|---|
| 1083 | April 7, 1999 (1999-04-07) | David Arquette, Jerry O'Connell | Susan Tedeschi |
|---|
| 1084 | April 8, 1999 (1999-04-08) | Will Ferrell, Jennifer Esposito, Mike Lupica | N/A |
|---|
| 1085 | April 9, 1999 (1999-04-09) | Jay Mohr, Jerry Springer | Citizen King |
|---|
| 1086 | April 13, 1999 (1999-04-13) | Martha Stewart, David Blaine | Todd Barry |
|---|
| 1087 | April 14, 1999 (1999-04-14) | Liv Tyler, Tim Meadows | Juvenile |
|---|
| 1088 | April 15, 1999 (1999-04-15) | Evander Holyfield, Marc Maron | Latin Playboys |
|---|
| 1089 | April 16, 1999 (1999-04-16) | Chris O'Donnell, Megan Mullally | David Feldman |
|---|
| 1090 | April 27, 1999 (1999-04-27) | Matt Lauer, Seth Green | Sugar Ray |
|---|
| 1091 | April 28, 1999 (1999-04-28) | Ana Gasteyer, George Stephanopoulos, Paula Cale | N/A |
|---|
| 1092 | April 29, 1999 (1999-04-29) | Michael J. Fox, Kevin James | Bill Burr |
|---|
| 1093 | April 30, 1999 (1999-04-30) | Matthew Broderick, Michael Moore | Godsmack |
|---|
| 1094 | May 4, 1999 (1999-05-04) | Al Roker, Louis C.K. | Madness |
|---|
| 1095 | May 5, 1999 (1999-05-05) | Aidan Quinn, Christa Miller | N/A |
|---|
| 1096 | May 6, 1999 (1999-05-06) | Julianne Moore, Reese Witherspoon, Scott Dikkers | N/A |
|---|
| 1097 | May 7, 1999 (1999-05-07) | Michael Rapaport | N/A |
|---|
| 1098 | May 11, 1999 (1999-05-11) | Paul Reiser, Chris Kattan | Old 97's |
|---|
| 1099 | May 12, 1999 (1999-05-12) | Janeane Garofalo & Ben Stiller, George Segal | N/A |
|---|
| 1100 | May 13, 1999 (1999-05-13) | Sarah Michelle Gellar, Camryn Manheim | Maria Bamford |
|---|
| 1101 | May 14, 1999 (1999-05-14) | Rob Lowe, Michelle Williams | Hootie & the Blowfish |
|---|
| 1102 | May 18, 1999 (1999-05-18) | Shannen Doherty, Timothy Dalton | N/A |
|---|
| 1103 | May 19, 1999 (1999-05-19) | Scott Thompson, Sable | N/A |
|---|
| 1104 | May 20, 1999 (1999-05-20) | Tom Selleck, William Shatner | Lewis Black |
|---|
| 1105 | May 21, 1999 (1999-05-21) | Helen Hunt, Keri Russell | Built to Spill |
|---|
| 1106 | May 25, 1999 (1999-05-25) | Gina Gershon, Craig Bierko | Greg Fitzsimmons |
|---|
| 1107 | May 26, 1999 (1999-05-26) | Steven Wright, Kari Wührer | Lit |
|---|
| 1108 | May 27, 1999 (1999-05-27) | Susan Lucci, Bill Bellamy | N/A |
|---|
| 1109 | May 28, 1999 (1999-05-28) | Damon Wayans, Gabrielle Reece | Kurt Andersen |
|---|
| 1110 | June 8, 1999 (1999-06-08) | Sarah Jessica Parker, George Thorogood | N/A |
|---|
| 1111 | June 9, 1999 (1999-06-09) | Geraldo Rivera, Rachel Griffiths | Upright Citizens Brigade |
|---|
| 1112 | June 10, 1999 (1999-06-10) | Scott Wolf, Alison Eastwood | Michael Moschen |
|---|
| 1113 | June 11, 1999 (1999-06-11) | Dave Foley, Joy Behar | Fountains of Wayne |
|---|
| 1114 | June 15, 1999 (1999-06-15) | Brian Dennehy, James McDaniel | Brian Regan |
|---|
| 1115 | June 16, 1999 (1999-06-16) | Noah Wyle, Jonathan Katz | Mike Ness |
|---|
| 1116 | June 17, 1999 (1999-06-17) | Nathan Lane, Wayne Knight, Joe Distler | N/A |
|---|
| 1117 | June 18, 1999 (1999-06-18) | Mike Myers | N/A |
|---|
| 1118 | June 22, 1999 (1999-06-22) | Patricia Arquette, Allen Covert | Seal |
|---|
| 1119 | June 23, 1999 (1999-06-23) | Bob Costas, Frederique | Robert Cray |
|---|
| 1120 | June 24, 1999 (1999-06-24) | Adam Sandler, Vince McMahon | N/A |
|---|
| 1121 | June 25, 1999 (1999-06-25) | #1121, | N/A |
|---|
| 1122 | July 6, 1999 (1999-07-06) | John Leguizamo, Tom Green | Margaret Smith |
|---|
| 1123 | July 7, 1999 (1999-07-07) | Dan Rather, Trey Parker and Matt Stone | Tom Petty & The Heartbreakers |
|---|
| 1124 | July 8, 1999 (1999-07-08) | Al Roker, Alyson Hannigan | Marc Maron |
|---|
| 1125 | July 9, 1999 (1999-07-09) | Chris Rock, Jennifer Esposito | Cubanismo |
|---|
| 1126 | July 13, 1999 (1999-07-13) | Jim Breuer, Harry Hamlin | Ronnie Dawson |
|---|
| 1127 | July 14, 1999 (1999-07-14) | Carmen Electra, Eugene Levy | Kelly Willis |
|---|
| 1128 | July 15, 1999 (1999-07-15) | Rudy Giuliani, Dwayne Perkins | Jeff Greenfield |
|---|
| 1129 | July 16, 1999 (1999-07-16) | Rupert Everett, Jerry Orbach | Gillian Welch & David Rawlings with Emmylou Harris |
|---|
| 1130 | July 20, 1999 (1999-07-20) | Kevin Nealon, Adrien Brody, Joey Ramone | N/A |
|---|
| 1131 | July 21, 1999 (1999-07-21) | Tori Spelling, Tony Randall | Moby |
|---|
| 1132 | July 22, 1999 (1999-07-22) | Jon Lovitz, Amy Adams | Ed Byrne |
|---|
| 1133 | July 23, 1999 (1999-07-23) | Janeane Garofalo, Chris Elliott | Public Enemy |
|---|
| 1134 | August 3, 1999 (1999-08-03) | Jeffrey Tambor, Harry Connick, Jr. | N/A |
|---|
| 1135 | August 4, 1999 (1999-08-04) | Pierce Brosnan, Al Goldstein | Jake Johannsen |
|---|
| 1136 | August 5, 1999 (1999-08-05) | Ana Gasteyer, Malcolm McDowell | Wanda Sykes |
|---|
| 1137 | August 6, 1999 (1999-08-06) | Matthew Broderick, Kristen Davis | Train |
|---|
| 1138 | August 10, 1999 (1999-08-10) | Scott Thompson, Ruby Wax | Jeff Beck |
|---|
| 1139 | August 11, 1999 (1999-08-11) | Darrell Hammond, Michael C. Williams | Gene Pompa |
|---|
| 1140 | August 12, 1999 (1999-08-12) | Claire Danes, Richard Kind | Todd Barry |
|---|
| 1141 | August 13, 1999 (1999-08-13) | Jarod Miller, Joely Fisher | Buckcherry |
|---|
| 1142 | August 17, 1999 (1999-08-17) | LL Cool J, Jamie Kennedy | Los Lobos |
|---|
| 1143 | August 18, 1999 (1999-08-18) | Jason Priestley, Roshumba | N/A |
|---|
| 1144 | August 19, 1999 (1999-08-19) | Hugh Grant, Esther Cañadas | Louis C.K. |
|---|
| 1145 | August 20, 1999 (1999-08-20) | Steve Austin, Michael Boltman | Diana Krall |
|---|