1. Jean-Claude Van Damme, Darryl Strawberry, Joe Cocker
Aired: Aug 31, 1998 During a segment comparing President Clinton's vacation to Dave's, a stockbro...
2. Beau Bridges, Terrell Davis, Squirrel Nut Zippers
Aired: Sep 1, 1998 Dave points out that the show has undergone budget cuts, which might explain ...
3. Terry Bradshaw, Jesse Jackson
Aired: Sep 2, 1998 Dave makes a lenghty rant about ""The Late Shift"" after an audience member a...
4. Ray Romano, Chris Cardone, Tom Agna
Aired: Sep 3, 1998 Alan Kalter comments on home run record that is being chased by Mark McGwire;...
5. Stupid Human Tricks, Jason Patric, Eve 6
Aired: Sep 4, 1998 During CBS Mailbag, Dave and the band play ""Let's Screw with Paul Shaffer's ...
6. Richard Simmons, Luisa Conlon
Aired: Sep 7, 1998 Junior Brown sits in with the band, while Biff reports from Busch Stadium in ...
7. Andie MacDowell, Willie Nelson
Aired: Sep 8, 1998 Biff makes another report from Busch Stadium, while Dave flirts with Andie Ma...
8. Tim Forneris, Stephen Dorff, Wynonna
Aired: Sep 9, 1998 Dave goes on a tirade about the CBS watermark on the lower right hand side of...
9. Charles Grodin, Paul Hopkins
Aired: Sep 10, 1998 Dave stuggles to grow a beard; Charles Grodin promotes his talk show; Dave ch...
10. Jack Hanna, Gretchen Mol, Nick Cave & The Bad Seeds
Aired: Sep 11, 1998 During CBS Mailbag, Paul, Tony, Biff and Sid announce that they're going to t...
11. Cindy Crawford, Jeff Greenfield, Hootie & The Blowfish
Aired: Sep 14, 1998 Dave congratulates the staff on the big Emmy win the previous night, then gri...
12. Ben Stiller, Jackie Chan, Vince Gill
Aired: Sep 15, 1998 Dave shows a (bogus) Mastercard ad starring Ken Starr; Biff goes to Chicago f...
13. Bill Cosby, George Hamilton
Aired: Sep 16, 1998 Biff brings in scissors for a tie trim; Calvert impersonates Hank Williams, J...
14. Denis Leary, George Hamilton
Aired: Sep 17, 1998 Dave apologizes for his affair with Angela Lansbury, while Biff apologizes fo...
15. Vince Vaughn, Brian Benben, Brian Setzer Orchestra
Aired: Sep 18, 1998 Dave makes another rant pertaining to the CBS Watermark; kid Geography whiz J...
16. Michael J. Fox, Evander Holyfield, Dixie Chicks
Aired: Sep 21, 1998 Dave talks about a Steak House Onion Machine, while Michael J. Fox promotes h...
17. Jennifer Lopez, Meredith Viera, Lyle Lovett
Aired: Sep 22, 1998 Dave shows a (bogus) ad for ESPN2's ""Xtreme Presidental Perjury,"" while J.L...
18. Stupid Pet Tricks, Marv Albert, Kevin James
Aired: Sep 23, 1998 A gag promo for the TV series ""Biffy, The Umpire Layer"" is declared the wor...
19. Howard Stern, Katie Holmes
Aired: Sep 24, 1998 Dave makes fun of Inky's summer camp outfit. Later, Howard Stern plays with ...
20. Jon Stewart, Jean Reno, Rob Zombie
Aired: Sep 25, 1998 A fawn walks onstage during CBS Mailbag; comedian Jon Stewart promotes ""The ...
21. Fran Drescher, Chris Kattan, Elvis Costello & Burt Bacharach
Aired: Sep 28, 1998 Musical guests Elvis Costello and Burt Bacharach perform ""I Just Don't Know ...
22. Chris Tucker, Faith Ford, Eagle Eye Cherry
Aired: Sep 29, 1998 Dave lets Inky go on a ""gum break;"" George Clarke is introduced as operator...
23. Kelsey Grammer, Nick Mason, Tony Bennett
Aired: Sep 30, 1998 Warren fills in for Paul (out for Yom Kippur); Kelsey Grammer brings out his ...
24. Drew Carey, Billy Connolly, Hedwig & The Angry Inch
Aired: Oct 1, 1998 Dennis, a baseball-bunting pig, waits throughout the show to shag some balls ...
25. Steve Martin, Cokie Roberts
Aired: Oct 2, 1998 During CBS Mailbag, Alan promotes ""Alan Kalter's Music To Make Love By,"" wh...
26. Kelly Preston, Peter Boyle, Semisonic
Aired: Oct 5, 1998 Dave experiments with how he can give the finger without being censored; Kell...
27. Elizabeth & Bob Dole, Joaquin Phoenix
Aired: Oct 6, 1998 Tony Mendez does a ""card trick""; Tito Puente contributes drumrolls to the T...
28. Jeff Goldblum, John Mellencamp
Aired: Oct 7, 1998 A new segment called ""This Day in Late Show History"" reveals that October 7...
29. Isabella Rossellini, Stephen Baldwin, George Miller
Aired: Oct 8, 1998 Dave takes a look at Tony's hands, which have marker ink all over them. Late...
30. Joan Lunden, Jeff Altman, Sheryl Crow
Aired: Oct 9, 1998 During CBS Mailbag, Tony bares his ass again, and The Foul-Mouthed Scenic Des...
31. Mark McGwire, Robert Benigni, Bruce Hornsby
Aired: Oct 19, 1998 The calvacade of mediocre crops continues as ""Joe Whitworth"" from Oregon wa...
32. State Fair Champions, Ringo Starr
Aired: Oct 20, 1998 It's Dave's 3000th show in late night, so he celebrates by bringing Charles G...
33. Jeff Daniels, David Cross, Mitch Hedberg
Aired: Oct 21, 1998 Dave and George Clarke go to Yankee Stadium, where the building engineer hits...
34. Danny Glover, Cal Ripken Jr., R.E.M.
Aired: Oct 22, 1998 Biff participates in more interviews in part two of his World Series report, ...
35. Naomi Campbell, David Wells, R.E.M.
Aired: Oct 23, 1998 Tony's eye itches, and Dave gives him a hard time for potentially screwing up...
36. Danny DeVito, Joe Torre, Eddie Brill
Aired: Oct 26, 1998 Four shirtless guys (spelling ""YANKS"") bring out the Top Ten; Danny DeVito ...
37. Martin Short, Eddie Izzard, Phish
Aired: Oct 27, 1998 Dave cons a Joe G's customer into appearing in a bogus campaign ad; Eddie Izz...
38. Daniel Baldwin, Todd Solondz, Phil Collins
Aired: Oct 28, 1998 Biff shows outtakes from last week's World Series reports, while director Tod...
39. Holly Hunter, Hunter S. Thompson, Garbage
Aired: Oct 29, 1998 Dave makes several jokes at the expense of septuagenarian spaceman John Glenn...
40. Ted Danson, Denny Brauer, Black Sabbath
Aired: Oct 30, 1998 Dave announces the names of staff members who will run in the New York City M...
41. Anthony Hopkins, Buzz Aldrin, Depeche Mode
Aired: Nov 2, 1998 New York Marathon winner John Kagwe runs through during the monologue, and is...
42. Queen Latifah, Ellie Lammer, Darrell Hammond
Aired: Nov 3, 1998 Dave gives bogus election results; the outside cam goes to Joe G's for anothe...
43. Adam Sandler, Jayson Williams, Soul Coughing
Aired: Nov 4, 1998 Dave shows a clip of new Minnesota governor Jesse ""The Body"" Ventura in the...
44. Denzel Washington, Father Mike Berner
Aired: Nov 5, 1998 Tony gets scolded for chewing gum; shortly after appearing on ""Know Your Cur...
45. George Pataki, Evan Metropoulis, P.J. Harvey
Aired: Nov 6, 1998 Dave chats with Evan Metropoulos, the 17-year-old CEO of the Bumble Bee Tuna ...
46. George Michael, Col. Gail Halverson, Hanson
Aired: Nov 9, 1998 Dave mentions that Meryl Streep, tonight's scheduled guest and star of the mo...
47. Luke Perry, Tom Wolfe, Jay-Z
Aired: Nov 10, 1998 Tom Wolfe promotes his first novel in 11 years, ""The Man In Full.""
48. Melanie Griffith, Walter Cronkite, Travis Tritt
Aired: Nov 11, 1998
49. Roma Downey, Kenneth Branagh, Goo Goo Dolls
Aired: Nov 12, 1998 Dave accuses Tony Mendez of goosing someone with a cue card; Roma Downey and ...
50. Donald Trump, Doug Flutie, Sarah Silverman
Aired: Nov 13, 1998
51. Kid Scientists, Cameron Diaz, Mariah Carey
Aired: Nov 16, 1998 Jayson Williams of the New Jersey Nets operates one of the cameras; a ""Kid S...
52. Will Smith, Jack Hanna
Aired: Nov 17, 1998 Dave once again takes away Tony's gum, while Paul tries to flirt with Monica ...
53. Cher, Jerry Springer
Aired: Nov 18, 1998
54. Christian Slater, Celine Dion & Bryan Adams
Aired: Nov 19, 1998 Drew Barrymore plugs ""Home Fries,"" while Celine Dion and Bryan Adams perfor...
55. Drew Barrymore, Siskel & Ebert
Aired: Nov 20, 1998 Todd Rundgren sits in, while Drew Barrymore walks onstage so that she can sho...
56. Helen Hunt, Ray Romano
Aired: Nov 23, 1998 James Cotton sits in; Dave discusses Dr. Kevorkian and the safest handling of...
57. Geena Davis, Martha Stewart, Roger Daltry
Aired: Nov 24, 1998 As he does almost every Thankgiving, Kreskin plays for pride in a little game...
58. Gwyneth Paltrow, Peter Berg, Bonnie Raitt
Aired: Nov 25, 1998 Jayson Williams of the Nets comments on the NBA lockout, then drops phony tur...
59. Michael Caine, Art Donavon, Jewel
Aired: Nov 26, 1998 Dave warns pedestrians (via his PA system) that the turkey is bad; a guy in t...
60. Salma Hayek, Marilyn Manson, Caroline Rhea
Aired: Nov 27, 1998 Dave fusses over his hair, then messes around with it. Later, Salma Hayek pl...
61. Patrick Stewart, Jon Stewart, Faith Hill
Aired: Dec 7, 1998 It's ""Stewart Night,"" as all the guests share the same last name despite no...
62. Greg Kinnear, Jane Horrocks, Reggie McFadden
Aired: Dec 8, 1998 Live from Times Square, it's ""Dick Clark's Rockin' December 9 Countdown."" ...
63. Tom Hanks, Brooklyn Philharmonic
Aired: Dec 9, 1998 Gerard plays an openly gay man in ""Who Asked For It?""; The Brooklyn Philhar...
64. Meg Ryan, Whitney Houston
Aired: Dec 10, 1998 Dave compares an electrician that played ""KYCE"" to John Elway. Also, Meg R...
65. Tom Brokaw, Famke Janssen, Emmylou Harris
Aired: Dec 11, 1998 Tom Brokaw drops by sporting a turtleneck sweater in lieu of his usual two-pi...
66. Robin Williams, Natalie Merchant
Aired: Dec 14, 1998 Dave explains the impeachment process; Robin Williams hosts the PBS special "...
67. Val Kilmer, Ricky Williams, Billy Bragg & Natalie Merchant
Aired: Dec 15, 1998 In lieu of a giant meatball, a pastrami sandwich is placed on top of the Late...
68. Susan Sarandon, Marc Weinberg, Vienna Choir Boys
Aired: Dec 16, 1998 While Paul and the Orchestra perform ""Songs for Pedestrians,"" Dave trims hi...
69. Jeff Goldblum, Angelina Jolie, Third Eye Blind
Aired: Dec 17, 1998 Live from sunny Los Angeles, it's ""Dick Clark's Rockin' Countdown to Decembe...
70. Julia Roberts, David Kelly
Aired: Dec 18, 1998 During Mailbag, Alan gives the audience an unusual egg nog recipe, while Dave...
71. Barbara Walters, Josh Hartnett, Cyndi Lauper
Aired: Dec 21, 1998 The latest roll call mentions ""Gus, who guy who owns property onstage"" and ...
72. Charles Grodin, John Witherspoon, Jessye Norman
Aired: Dec 22, 1998 Dave refunds $50 to an audience lady with a Late Show sweatshirt; a Joe G's c...
73. John Travolta, Darlene Love
Aired: Dec 23, 1998 Soon-to-be-traded Yankees pitcher David Wells sits in the audience; the first...
74. Chazz Palminteri, Ann Curry, Rufus Wainwright
Aired: Dec 28, 1998 Dave talks about the recent successes of the New York Jets, so Harold Larkin ...
75. James Woods, David Brenner, Cast of But Boy Could He Sing
Aired: Dec 29, 1998 Bisbee, North Dakota is investigated in the latest edition of ""Biff Henderso...
76. Jay Thomas, Vinny Testaverde, Patti Smith
Aired: Dec 30, 1998 Throughout the night, Chicago announcer ""Ray Clay"" fills in for Alan, makin...
77. Stupid Human Tricks, Nathan Lane, St. Luke's Bottle Band
Aired: Dec 31, 1998 Kamarr the Discount Magician makes one last appearance.
78. Jon Voight, Jena Malone, Louie C.K.
Aired: Jan 1, 1999 Jon Voight promotes two films, ""Enemy of the State"" and ""Varsity Blues.""
79. Sarah Jessica Parker, David Remnick, Bryan Callan
Aired: Jan 4, 1999 Biff pretends to stand in Times Square again, this time reporting about the w...
80. Jennifer Jason Leigh, Liam Aiken, Greg Behrendt
Aired: Jan 5, 1999 Biff just can't get enough of the green screen in the hallway; tonight's part...
81. Mira Sorvino, Terry Bradshaw
Aired: Jan 6, 1999 It's time for ""How Many Guys in Mouse Suits Can Fit into a Dunkin' Donuts?""...
82. Lisa Kudrow, Terry Bradshaw, Jason Kuller
Aired: Jan 7, 1999 Dave announces the new name of the show will be ""David Letterman's Countdown...
83. Jon Stewart, Marv Albert, Jim Gaffigan
Aired: Jan 8, 1999 ""David Letterman's Countdown to the Millennium,"" Day 2: Paul declares that ...
84. Gillian Anderson, Charlie Rose, Black Crowes
Aired: Jan 11, 1999 Sitting in with the CBS Orchestra tonight: the shirtless guy who was the ""T"...
85. Robert Duvall, Al Franken, B.B. King
Aired: Jan 12, 1999 During ""Small Town News,"" Dave sports a paper mustache.
86. Conan O'Brian, Alanis Morrisette
Aired: Jan 13, 1999 Tonight's ""Paul Shaffer Millennium Prediction"": health spas will not charge...
87. William Baldwin, Trisha Yearwood, Scott Ferrall
Aired: Jan 14, 1999 William Baldwin promotes ""Virus,"" while Biff rescues Dave's coffee mug afte...
88. Jack Hanna, Patricia Arquette
Aired: Jan 15, 1999 Mailbag: Tony mentions he's taken up acting, then shows two remarkably simila...
89. Yasmine Bleeth, Adam Carolla, James Brown
Aired: Jan 25, 1999
90. Alicia Silverstone, D.L. Hughley, Second Hand
Aired: Jan 26, 1999 Dave says a focus group doesn't like his ""Countdown to the Millennium"" segm...
91. Sophia Loren, The Mavericks
Aired: Jan 27, 1999 Dave and Paul discuss William Wood Lee Shaffer's diapers. Later, Paul interr...
92. Bill Murray, Shania Twain
Aired: Jan 28, 1999 Biff shows up with a tie for a ""Know Your Current Events"" contestant; Bill ...
93. Cate Blanchett, Jason Schwartzman, Brandy
Aired: Jan 29, 1999 Dave announces he and Paul are trying to establish a video nexus; during Mail...
94. Bill Cosby, Brendon Fraser, Ricky Scruggs & Vince Gill
Aired: Feb 1, 1999 It's the seventeenth anniversary of Dave's debut in late night, and what is h...
95. Tom Arnold, David Brenner, Catherine Bell
Aired: Feb 2, 1999 Dave mentions that through the wonders of science, Paul Shaffer had another b...
96. Tom Brokaw, Sean Patrick Flanery, Creed
Aired: Feb 3, 1999 Dave and Paul spend ten minutes discussing the new and improved ""Late Show""...
97. Mel Gibson, Laetitia Casta, Fresh Step
Aired: Feb 4, 1999 Dave reads about Bucknell University for a ""KYCE"" participant; Laetitia Cas...
98. Stupid Pet Tricks, Martha Stewart, Mitch Hedberg
Aired: Feb 5, 1999 Nile Rogers fills in for both Felicia and Will Lee, who are both sick; Martha...
99. Michael J. Fox, Rev. John & Ellena Cobb, Willie Nelson
Aired: Feb 8, 1999 ""Biff Henderson's America"" makes a quick stop in Baker, Nevada. Also, Dave...
100. Jeff Daniels, Fernanda Montenegro, Monica
Aired: Feb 9, 1999 Dave chats with (live via satellite) Al at Prestige Luggage Company in Dallas...
101. Robin Wright Penn, Richard Kind, Chris Isaak
Aired: Feb 10, 1999 Dave rants about the internet, while Bob Borden literally searches for a vale...
102. Sandra Bullock, James Carville, Hootie & The Blowfish
Aired: Feb 11, 1999 Orlando Antigua of the Harlem Globetrotters helps out during ""Know Your Curr...
103. Richard Simmons, Sarah O'Hare, Ondar
Aired: Feb 12, 1999 Dave discusses signature sign-offs and announces his new one will be ""Keep a...
104. Bette Midler, David Hyde Pierce
Aired: Feb 15, 1999 Tonight marks the debut of ""Alan Kalter's Secret Word."" Tonight's utteranc...
105. Andy Garcia, Tara Lipinksi, Wendy Liebman
Aired: Feb 16, 1999 Lou Soloff of Blood, Sweat and Tears sits in with the horn section; Alan's se...
106. Andie MacDowell, Mike Judge, Julian Lennon
Aired: Feb 17, 1999 The secret word is ""mongoose""; ten West Point cadet presents the Top Ten; J...
107. Magic Johnson, Jake Gyllenhaal, Jewel
Aired: Feb 18, 1999 The secret word is ""hydraulic""; Dave gives a photographer in the audience a...
108. Lauren Bacall, Greg Smith, Sugar Ray
Aired: Feb 19, 1999 The secret word is ""buttress""; during Mailbag, Dave and Linda Tripp appear ...
109. Matthew Broderick, Sheryl Crow
Aired: Feb 22, 1999 Dave takes five minutes to comment on the sudden death of Gene Siskel, then s...
110. Kid Scientists, Jesse Ventura
Aired: Feb 23, 1999 Alan's secret word is ""bobcat,"" and the jackpot now stands at ""seven hundr...
111. Uma Thurman, Tom Green, De La Guarda
Aired: Feb 24, 1999 The secret word is ""barnacle;"" Dave answers a phone call from Sweden; in a ...
112. Eriq La Salle, Homer Hickman, Blondie
Aired: Feb 25, 1999 The secret word is ""corpuscular."" Meanwhile, Dave chats with Homer Hickam, ...
113. James Coburn, Will Ferrall, Marvelous Three
Aired: Feb 26, 1999 The secret word is ""combustible,"" and the stakes have been raised to an eve...
114. Brooke Shields, Peter Hillary
Aired: Mar 1, 1999
115. Ian McKellen, Reese Witherspoon, The Roots & Erykah Badu
Aired: Mar 2, 1999 The secret word is ""saluki""; live via satellite, the employees of the Uncla...
116. Kid Turkey Callers, Mark Wahlberg, Fresh Step
Aired: Mar 3, 1999 Dave rants about tonight's Barbara Walters/Monica Lewinsky interview; the sec...
117. Billy Crystal, George Miller
Aired: Mar 4, 1999 The secret word is ""viscous,"" while George Miller rants about the media.
118. Chazz Palminteri, Jeff Altman, Everclear
Aired: Mar 5, 1999 The secret word is ""melancholia,"" while ""Oprah"" (Pat Farmer) flirts with ...
119. Norm MacDonald, Jeff Beck
Aired: Mar 22, 1999 The secret word is ""lederhosen""; the second-ever ""Alan Kalter's Where Are ...
120. Elizabeth Hurley, Katie Holmes, Cake
Aired: Mar 23, 1999 The secret word is ""Ionosphere,"" with the prize now standing at ""$1700 dam...
121. Stupid Human Tricks, Craig Kilborn, Emmylou Harris, Linda Rondstadt, and Dolly Parton
Aired: Mar 24, 1999 The secret word is ""shipjack""; Dave shows a meat identification kit, comple...
122. Elton John, Henry Kissinger, LeAnn Rimes
Aired: Mar 25, 1999 The secret word is ""bilious,"" which is coincidental because Dave feels unde...
123. Ron Howard, Charlotte Church
Aired: Mar 26, 1999 Dave bids farewell to Tom Snyder (his last show aired that night), then says ...
124. Marv Albert, Diane Lane, Blur
Aired: Mar 29, 1999 Dave hollers about 60 Minutes, then claims that somebody won the Secret Word ...
125. Laurence Fishburne, Sister Carol Anne Corley, Wilco
Aired: Mar 30, 1999 The opening sequence is altered; the secret word is ""taconite""; Dave chats ...
126. Steve Martin & Goldie Hawn, Jim Calhoun, Joe Henry
Aired: Mar 31, 1999 The secret word is ""sociopathic,"" while Steve Martin and Goldie Hawn promot...
127. Dennis Hopper, Jason Nastke, The Corrs
Aired: Apr 1, 1999 The secret word is ""nemonurwingy,"" but Dave accuses Alan of making it up (w...
128. Marilu Henner, Master P, Greg Fitzsimmons
Aired: Apr 2, 1999 Charlie Daniels sits in on fiddle; the secret word is ""mahagony""; comedian/...
129. Charles Grodin, David Arquette, Willie Nelson, Lyle Lovett, and Kris Kristofferson
Aired: Apr 5, 1999 The secret word is ""flange""; Dave holds up a certificate that makes Late Sh...
130. Drew Barrymore, Scott Wolf, Barenaked Ladies
Aired: Apr 6, 1999 The secret word is ""millipede""; right after the second-ever edition of ""Kn...
131. Lennox Lewis, Dr. Bertrand Piccard & Brian Jones
Aired: Apr 7, 1999 Throughout the night, local teens with learner's permits parallel park on 53r...
132. George Stephanopoulos, Molly Shannon, Andrea Bocelli
Aired: Apr 8, 1999 The secret word is ""ischemia,"" while SNL star Molly Shannon promotes Never ...
133. Bill Maher, Khalid El-Amin, Marc Maron
Aired: Apr 9, 1999 Paul makes his second ""Countdown to the Millennium"" prediction since the de...
134. Elle Macpherson, Don Zimmer, John Mellencamp
Aired: Apr 12, 1999 Paul announces celebrities will come by all evening to wish Dave a happy birt...
135. Kevin Spacey, Tom Petty & The Heartbreakers
Aired: Apr 13, 1999 The secret word is ""hegemony,"" and Dave doubles the current jackpot from $1...
136. Kate Winslet, Darrell Hammond, Mandy Barnett
Aired: Apr 14, 1999 The secret word is ""quadricentennial,"" and after doubling the stakes on las...
137. David Spade, Tim Couch, Eagle-Eye Cherry
Aired: Apr 15, 1999 Dave mentions the sudden and untimely death of Bill Wendell; the secret word ...
138. John Cusack, Jack Hanna
Aired: Apr 16, 1999 A technical difficulty turns Dave's face and tie blue during the monologue; t...
139. Matthew Broderick, Ben Stein, The Cranberries
Aired: Apr 26, 1999 Dave discusses the various bars and/or grills that have been next door to the...
140. Martin Lawrence, Michelle Williams, Eddie Brill
Aired: Apr 27, 1999 Dave claims there was a secret word winner last night, then brings out Connec...
141. Dustin Hoffman, Mary Steenburgen, Ben Folds Five
Aired: Apr 28, 1999 The secret word is ""boat""; Paul, Felecia, Will, and Sid perform ""Songs for...
142. Ted Danson, Sarah Ferguson, Madness
Aired: Apr 29, 1999 The secret word is ""carrot,"" and Dave introduces another supposed winner (w...
143. Glenn Close, George Hamilton, Elvis Crespo
Aired: Apr 30, 1999 In honor of tonight's audience, the backdrop is altered to show the skyline o...
144. Tom Brokaw, Robbie Williams
Aired: May 3, 1999 Dave claims he's filed a $100 million lawsuit against the surgeon general; Da...
145. Earvin Magic Johnson, Sara Gentile, Silverchair
Aired: May 4, 1999 The secret word is ""incinerate""; Paul Fiore tries to parallel-park outside;...
146. Denny Brauer, Kelly Willis, Jesse Jackson
Aired: May 5, 1999 The secret word is ""undershirt""; Dave shows (bogus) footage of Roberto Beni...
147. Brendan Fraser, Jesse Jackson, Bonnie Raitt
Aired: May 6, 1999 Cold opening: Jesse Jackson makes an insincere apology to Dave for his tardin...
148. Kelsey Grammer, Steve Earle and the Del McCoury Band
Aired: May 7, 1999 In honor of tonight's travel-weary audience (everybody's from Nashville), Bif...
149. Stupid Pet Tricks, Janeane Garofalo, Brian Regan
Aired: May 10, 1999 The secret word is ""ball""; an audience member is stifled by a barbershop qu...
150. Ben Stiller, Camryn Manheim, Eve 6
Aired: May 11, 1999 Thirteen-year-old blues phenomenon Ben Robinson sits in; the secret word is "...
151. Kathie Lee Gifford, Deana Carter
Aired: May 12, 1999 Dave makes a nonsense rant about Barry Manilow; the secret word is ""winky"";...
152. Kevin Kline, Leelee Sobieski, Beth Orton
Aired: May 13, 1999 Dave bring out the seven supposed winners of last night's secret word contest...
153. Bill Cosby, Jon Favreau
Aired: May 14, 1999 With tonight's audience being from the City of Brotherly Love, Biff heads to ...
154. Julia Roberts, Alice Cooper
Aired: May 17, 1999 The secret word is ""molar,"" while Dave measures Julia Roberts' waist.
155. Keri Russell, Aretha Franklin
Aired: May 18, 1999 Dave calls Aloha Meats in Honolulu to see if they answer the phone by saying ...
156. Tom Selleck, Bob Barker, Leon Russell
Aired: May 19, 1999 The secret word is ""turf""; various members of the staff appear in a series ...
157. Helen Hunt, Courtney Love, Hole
Aired: May 20, 1999 The secret word is ""Alan""; Dave shows a one dollar bill folded so it would ...
158. Natalie Portman, Tom Everett Scott, J. Geils Band
Aired: May 21, 1999 Tonight's audience hails from Boston, Massachusetts. The backdrop, as always...
159. Harry Connick Jr., Damon Wayans
Aired: May 24, 1999 Dave goes on a fury as to what constitutes the dinners given as prizes during...
160. Kate Capshaw, Britney Spears
Aired: May 25, 1999 Dave tries calling Hawaii again; the secret word is ""asparagus""; Kate Capsh...
161. Kid Scientists, Sarah Jessica Parker, Mary Chapin Carpenter
Aired: May 26, 1999 Anton is again introduced as Buddy Rich, Jr.; Paul pays $102,000,000 for a ti...
162. Bill Murray, Everlast
Aired: May 27, 1999 Jay Johnson wins the secret word ""contest"" again; throughout the night, Lou...
163. Jennifer Lopez, Ira Glass
Aired: May 28, 1999 The secret word is ""bituminous""; Lou Rawls continues to lounge in the green...
164. Dan Rather, Nancy Mace, Randy Newman
Aired: Jun 7, 1999 Tonight's secret word (""emetic"") is now sponsored by a lawn-watering device...
165. Jeff Foxworthy, Kristin Davis, Snoop Dogg
Aired: Jun 8, 1999 The Hosie Cow Secret Word is ""escarpment""; Dave plays a new game at Joe G's...
166. Timothy Hutton, Christine Lahti, Cast of It Ain't Nothing But the Blues
Aired: Jun 9, 1999 The Hosie Cow Secret Word is ""whippy""; last night's winner ""Barbara Sanche...
167. Ray Romano, Jewel
Aired: Jun 10, 1999 After appearing in an ad for Hosie Cow, Alan announces that the secret word i...
168. Heather Graham, David Wells
Aired: Jun 11, 1999 Edgar Winter sits in; the Hosie Cow Secret Word is ""dick""; Heather Graham p...
169. Tim Robbins, Oscar De La Hoya, Dane Cook
Aired: Jun 14, 1999 The Hosie Cow Secret Word is ""amputation""; the latest roll call introduces ...
170. Roseanne, Susan Tedeschi
Aired: Jun 15, 1999 The Hosie Cow Secret Word is ""dick"" again, but it's eventually changed to "...
171. David Schwimmer, Brandi Chastain, Seth Green
Aired: Jun 16, 1999 The Hosie Cow Secret Word is ""pigment,"" while Dave chats (and becomes infat...
172. Mike Myers, Ben Lee
Aired: Jun 17, 1999 Al Gore appears on ""The Paul Shaffer Show""; The Hosie Cow Secret Word is ""...
173. Julianna Margulies, Jon Stewart
Aired: Jun 18, 1999 Anton is introduced as Buddy Rich Jr., the ""bastard son"" of the legendary j...
174. Felicity Huffman, Andy Dick, Elvis Costello
Aired: Jun 21, 1999 The secret word (""rodeo"") is now sponsored by Larry King, whom according to...
175. Adam Sandler, Missy Elliot
Aired: Jun 22, 1999 The Larry King Secret Word is ""gabardine,"" and is followed by stock footage...
176. Geri Halliwell, Richard Belzer
Aired: Jun 23, 1999 Jimmy Vaughan sits in; the Larry King Secret Word is ""entropic""; after an u...
177. Rudolph Giuliani, Leslie Mann, The Pretenders
Aired: Jun 24, 1999 The Larry King Secret Word is ""linguine."" Also, to counteract with Hillary...
178. Joey Lauren Adams, Spike Lee, Santana
Aired: Jun 25, 1999 The Larry King Secret Word is ""peptide""; Carlos Santana and Rob Thomas of M...
179. Colin Powell, Maurice Green
Aired: Jun 28, 1999 Tonight's Secret Word (""bird"") is brought to you by David Letterman's Women...
180. Mira Sorvino, Lyle Lovett
Aired: Jun 29, 1999 The World Cup Soccer Team Secret Word is ""oozing""; Montana park ranger (and...
181. Piedmont Bird Callers, Avery Johnson, June Carter Cash
Aired: Jun 30, 1999 The Larry King/Women's Soccer Secret Word is ""peripatetic""; a bird caller f...
182. Calista Flockhart, Jack Hannah
Aired: Jul 1, 1999 The Larry King/Women's Soccer Secret Word is ""highoeyazmuhoodhee""; Calista ...
183. Stupid Human Tricks, John Leguizamo, Ziggy Marley & The Melody Makers
Aired: Jul 2, 1999 The Larry King/Women's Soccer Secret Word is ""pony""; during Mailbag, Biff, ...
184. John McEnroe, George Jones
Aired: Jul 5, 1999 Dave shows footage of a taxi literally crashing the staff cookout out on 53rd...
185. Chris Rock, Sixpence None the Richer
Aired: Jul 6, 1999 An audience member attempts to button Dave's jacket; the Dan Quayle/Larry Kin...
186. Lindsay Davenport, Oliver Platt, Jeffrey Ross
Aired: Jul 7, 1999 Dave replies to a Zagat's survey; the Women's Soccer Secret Word is ""pestile...
187. Jay Thomas, Jason Briggs
Aired: Jul 8, 1999 The Secret Word is ""prick,"" with the stock footage of the baby owls eating ...
188. Naomi Campbell, Jimmie Walker, Lucinda Williams
Aired: Jul 9, 1999 Dave points out that Paul is dressed from head to toe in white tonight, inclu...
189. Don Rickles, Dave Mirra, Patty Griffin
Aired: Jul 19, 1999 The Larry King/Dan Quayle Secret Word is ""sphygmomanometer""; Dave briefly c...
190. U.S. 1999 World Cup Women's Soccer Team, Jim Gaffigan
Aired: Jul 20, 1999 The Dan Quayle/Larry King Secret Word is ""pie""; Dave finally meets the enti...
191. Matthew Broderick, Dennis Regan
Aired: Jul 21, 1999 The Hillary Clinton/Larry King Secret Word is ""mommy""; Dave asks a question...
192. Catherine Zeta-Jones, Buzz Aldrin, Jamiroquai
Aired: Jul 22, 1999 The Hillary Clinton/Larry King Secret Word is ""meehnkee""; Dave ""performs""...
193. Charles Grodin, Alanis Morrisette
Aired: Jul 23, 1999 Paul asks what the point of the Secret Word is, and after it's revealed (""th...
194. Ted Koppel, Isabella Rossellini, Macy Gray
Aired: Jul 26, 1999 Paul complains about the heat at Woodstock '99; Dave brags about Max Pappas a...
195. National Hollerin' Champions, Garry Marshall, Los Lobos
Aired: Jul 27, 1999 Buckwheat Zydeco (nee Stanley Durrell) sits in on accordion; throughout the n...
196. Samuel L. Jackson, Rita Wilson, Pete Townshend & Eddie Vedder
Aired: Jul 28, 1999 Biff helps out pedestrians walking on 53rd Street; Dave asks Paul about proje...
197. Bruce Willis, Heidi Klum
Aired: Jul 29, 1999 ""Paul Shaffer's Countdown to the Millennium"" makes its triumphant return to...
198. Lance Armstrong, Barry White
Aired: Jul 30, 1999 Dave chats with Tour de France winner and cancer survivor Lance Armstrong; Pa...
199. Pierce Brosnan, Saffron Burrows, Jim Jeter
Aired: Aug 2, 1999 It's a very special night as Jim Jeter is about to log his one millionth mile...
200. Tom Arnold, Q-Tip & Busta Rhymes
Aired: Aug 3, 1999 Dave takes the outside cam to Joe G's for another round of ""Stop Calling Me ...
201. Dave Foley, Jonathan Witherspoon, Old 97's
Aired: Aug 4, 1999 Dave shows the audience some stuff he bought on his recent vacation in a segm...
202. William H. Macy, George Miller, The Pretenders
Aired: Aug 5, 1999 Dave repeatedly shows footage of the Taco Bell chihuahua saying ""funkaliciou...
203. Ray Romano, Jeff Altman
Aired: Aug 6, 1999 During CBS Mailbag, Alan punches Dave. Later, Dave's former ""Starland Vocal...
204. Regis Philbin, Dave Attell
Aired: Aug 9, 1999 Paul refers to Regis as a bastard, only for the ""Millionaire"" host to retal...
205. Claire Danes, Smash Mouth
Aired: Aug 10, 1999 Kreskin's knowledge of 70's backup singers is tested in a segment called ""Co...
206. Hugh Grant, The Mavericks
Aired: Aug 11, 1999 Dave announces that a crack in the building next door caused a temporary evac...
207. Rene Russo, Tori Amos
Aired: Aug 12, 1999 Dave takes up an offering for a preacher who played ""Who Your Deer Repellant...
208. Shaquille O'Neal, Helen Mirren
Aired: Aug 13, 1999 During CBS Mailbag, Inky Mendez announces his candidacy for the US Senate, wh...
209. Tony Danza, Katie Holmes, Robert Palmer
Aired: Aug 16, 1999 A shirtless Vince DeMentri interviews people on the street, asking them what ...
210. Lara Flynn Boyle, David Brenner, Everclear
Aired: Aug 17, 1999 Dave announces that tonight, ""We're going to have good old-fashioned fun"": ...
211. Andie MacDowell, French Stewart, Tom Dreesen
Aired: Aug 18, 1999 Terence Blanchard sits in with the band, while Olympic diver Kathy Pesek does...
212. Alec Baldwin, Dwight Yoakam
Aired: Aug 19, 1999 Dave announces that tonight is the premiere of ""Late Show Who Wants to be a ...
213. Albert Brooks, Omar Epps
Aired: Aug 20, 1999 Dave announces that after 6 years and 1,278 shows on CBS, he now wants to be ...