1. Jean-Claude Van Damme, Darryl Strawberry, Joe Cocker
Aired: Aug 31, 1998During a segment comparing President Clinton's vacation to Dave's, a stockbro...
2. Beau Bridges, Terrell Davis, Squirrel Nut Zippers
Aired: Sep 1, 1998Dave points out that the show has undergone budget cuts, which might explain ...
3. Terry Bradshaw, Jesse Jackson
Aired: Sep 2, 1998Dave makes a lenghty rant about ""The Late Shift"" after an audience member a...
4. Ray Romano, Chris Cardone, Tom Agna
Aired: Sep 3, 1998Alan Kalter comments on home run record that is being chased by Mark McGwire;...
5. Stupid Human Tricks, Jason Patric, Eve 6
Aired: Sep 4, 1998During CBS Mailbag, Dave and the band play ""Let's Screw with Paul Shaffer's ...
6. Richard Simmons, Luisa Conlon
Aired: Sep 7, 1998Junior Brown sits in with the band, while Biff reports from Busch Stadium in ...
7. Andie MacDowell, Willie Nelson
Aired: Sep 8, 1998Biff makes another report from Busch Stadium, while Dave flirts with Andie Ma...
8. Tim Forneris, Stephen Dorff, Wynonna
Aired: Sep 9, 1998Dave goes on a tirade about the CBS watermark on the lower right hand side of...
9. Charles Grodin, Paul Hopkins
Aired: Sep 10, 1998Dave 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, 1998During 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, 1998Dave congratulates the staff on the big Emmy win the previous night, then gri...
12. Ben Stiller, Jackie Chan, Vince Gill
Aired: Sep 15, 1998Dave shows a (bogus) Mastercard ad starring Ken Starr; Biff goes to Chicago f...
13. Bill Cosby, George Hamilton
Aired: Sep 16, 1998Biff brings in scissors for a tie trim; Calvert impersonates Hank Williams, J...
14. Denis Leary, George Hamilton
Aired: Sep 17, 1998Dave apologizes for his affair with Angela Lansbury, while Biff apologizes fo...
15. Vince Vaughn, Brian Benben, Brian Setzer Orchestra
Aired: Sep 18, 1998Dave makes another rant pertaining to the CBS Watermark; kid Geography whiz J...
16. Michael J. Fox, Evander Holyfield, Dixie Chicks
Aired: Sep 21, 1998Dave talks about a Steak House Onion Machine, while Michael J. Fox promotes h...
17. Jennifer Lopez, Meredith Viera, Lyle Lovett
Aired: Sep 22, 1998Dave shows a (bogus) ad for ESPN2's ""Xtreme Presidental Perjury,"" while J.L...
18. Stupid Pet Tricks, Marv Albert, Kevin James
Aired: Sep 23, 1998A gag promo for the TV series ""Biffy, The Umpire Layer"" is declared the wor...
19. Howard Stern, Katie Holmes
Aired: Sep 24, 1998Dave makes fun of Inky's summer camp outfit. Later, Howard Stern plays with ...
20. Jon Stewart, Jean Reno, Rob Zombie
Aired: Sep 25, 1998A fawn walks onstage during CBS Mailbag; comedian Jon Stewart promotes ""The ...
21. Fran Drescher, Chris Kattan, Elvis Costello & Burt Bacharach
Aired: Sep 28, 1998Musical guests Elvis Costello and Burt Bacharach perform ""I Just Don't Know ...
22. Chris Tucker, Faith Ford, Eagle Eye Cherry
Aired: Sep 29, 1998Dave lets Inky go on a ""gum break;"" George Clarke is introduced as operator...
23. Kelsey Grammer, Nick Mason, Tony Bennett
Aired: Sep 30, 1998Warren 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, 1998Dennis, a baseball-bunting pig, waits throughout the show to shag some balls ...
25. Steve Martin, Cokie Roberts
Aired: Oct 2, 1998During CBS Mailbag, Alan promotes ""Alan Kalter's Music To Make Love By,"" wh...
26. Kelly Preston, Peter Boyle, Semisonic
Aired: Oct 5, 1998Dave experiments with how he can give the finger without being censored; Kell...
27. Elizabeth & Bob Dole, Joaquin Phoenix
Aired: Oct 6, 1998Tony Mendez does a ""card trick""; Tito Puente contributes drumrolls to the T...
28. Jeff Goldblum, John Mellencamp
Aired: Oct 7, 1998A new segment called ""This Day in Late Show History"" reveals that October 7...
29. Isabella Rossellini, Stephen Baldwin, George Miller
Aired: Oct 8, 1998Dave 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, 1998During CBS Mailbag, Tony bares his ass again, and The Foul-Mouthed Scenic Des...
31. Mark McGwire, Robert Benigni, Bruce Hornsby
Aired: Oct 19, 1998The calvacade of mediocre crops continues as ""Joe Whitworth"" from Oregon wa...
32. State Fair Champions, Ringo Starr
Aired: Oct 20, 1998It'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, 1998Dave and George Clarke go to Yankee Stadium, where the building engineer hits...
34. Danny Glover, Cal Ripken Jr., R.E.M.
Aired: Oct 22, 1998Biff participates in more interviews in part two of his World Series report, ...
35. Naomi Campbell, David Wells, R.E.M.
Aired: Oct 23, 1998Tony's eye itches, and Dave gives him a hard time for potentially screwing up...
36. Danny DeVito, Joe Torre, Eddie Brill
Aired: Oct 26, 1998Four shirtless guys (spelling ""YANKS"") bring out the Top Ten; Danny DeVito ...
37. Martin Short, Eddie Izzard, Phish
Aired: Oct 27, 1998Dave 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, 1998Biff shows outtakes from last week's World Series reports, while director Tod...
39. Holly Hunter, Hunter S. Thompson, Garbage
Aired: Oct 29, 1998Dave makes several jokes at the expense of septuagenarian spaceman John Glenn...
40. Ted Danson, Denny Brauer, Black Sabbath
Aired: Oct 30, 1998Dave 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, 1998New York Marathon winner John Kagwe runs through during the monologue, and is...
42. Queen Latifah, Ellie Lammer, Darrell Hammond
Aired: Nov 3, 1998Dave gives bogus election results; the outside cam goes to Joe G's for anothe...
43. Adam Sandler, Jayson Williams, Soul Coughing
Aired: Nov 4, 1998Dave shows a clip of new Minnesota governor Jesse ""The Body"" Ventura in the...
44. Denzel Washington, Father Mike Berner
Aired: Nov 5, 1998Tony gets scolded for chewing gum; shortly after appearing on ""Know Your Cur...
45. George Pataki, Evan Metropoulis, P.J. Harvey
Aired: Nov 6, 1998Dave chats with Evan Metropoulos, the 17-year-old CEO of the Bumble Bee Tuna ...
46. George Michael, Col. Gail Halverson, Hanson
Aired: Nov 9, 1998Dave mentions that Meryl Streep, tonight's scheduled guest and star of the mo...
47. Luke Perry, Tom Wolfe, Jay-Z
Aired: Nov 10, 1998Tom Wolfe promotes his first novel in 11 years, ""The Man In Full.""
48. Melanie Griffith, Walter Cronkite, Travis Tritt
Aired: Nov 11, 199849. Roma Downey, Kenneth Branagh, Goo Goo Dolls
Aired: Nov 12, 1998Dave accuses Tony Mendez of goosing someone with a cue card; Roma Downey and ...
50. Donald Trump, Doug Flutie, Sarah Silverman
Aired: Nov 13, 199851. Kid Scientists, Cameron Diaz, Mariah Carey
Aired: Nov 16, 1998Jayson Williams of the New Jersey Nets operates one of the cameras; a ""Kid S...
52. Will Smith, Jack Hanna
Aired: Nov 17, 1998Dave once again takes away Tony's gum, while Paul tries to flirt with Monica ...
53. Cher, Jerry Springer
Aired: Nov 18, 199854. Christian Slater, Celine Dion & Bryan Adams
Aired: Nov 19, 1998Drew Barrymore plugs ""Home Fries,"" while Celine Dion and Bryan Adams perfor...
55. Drew Barrymore, Siskel & Ebert
Aired: Nov 20, 1998Todd Rundgren sits in, while Drew Barrymore walks onstage so that she can sho...
56. Helen Hunt, Ray Romano
Aired: Nov 23, 1998James Cotton sits in; Dave discusses Dr. Kevorkian and the safest handling of...
57. Geena Davis, Martha Stewart, Roger Daltry
Aired: Nov 24, 1998As he does almost every Thankgiving, Kreskin plays for pride in a little game...
58. Gwyneth Paltrow, Peter Berg, Bonnie Raitt
Aired: Nov 25, 1998Jayson Williams of the Nets comments on the NBA lockout, then drops phony tur...
59. Michael Caine, Art Donavon, Jewel
Aired: Nov 26, 1998Dave 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, 1998Dave fusses over his hair, then messes around with it. Later, Salma Hayek pl...
61. Patrick Stewart, Jon Stewart, Faith Hill
Aired: Dec 7, 1998It's ""Stewart Night,"" as all the guests share the same last name despite no...
62. Greg Kinnear, Jane Horrocks, Reggie McFadden
Aired: Dec 8, 1998Live from Times Square, it's ""Dick Clark's Rockin' December 9 Countdown."" ...
63. Tom Hanks, Brooklyn Philharmonic
Aired: Dec 9, 1998Gerard plays an openly gay man in ""Who Asked For It?""; The Brooklyn Philhar...
64. Meg Ryan, Whitney Houston
Aired: Dec 10, 1998Dave compares an electrician that played ""KYCE"" to John Elway. Also, Meg R...
65. Tom Brokaw, Famke Janssen, Emmylou Harris
Aired: Dec 11, 1998Tom Brokaw drops by sporting a turtleneck sweater in lieu of his usual two-pi...
66. Robin Williams, Natalie Merchant
Aired: Dec 14, 1998Dave explains the impeachment process; Robin Williams hosts the PBS special "...
67. Val Kilmer, Ricky Williams, Billy Bragg & Natalie Merchant
Aired: Dec 15, 1998In 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, 1998While Paul and the Orchestra perform ""Songs for Pedestrians,"" Dave trims hi...
69. Jeff Goldblum, Angelina Jolie, Third Eye Blind
Aired: Dec 17, 1998Live from sunny Los Angeles, it's ""Dick Clark's Rockin' Countdown to Decembe...
70. Julia Roberts, David Kelly
Aired: Dec 18, 1998During Mailbag, Alan gives the audience an unusual egg nog recipe, while Dave...
71. Barbara Walters, Josh Hartnett, Cyndi Lauper
Aired: Dec 21, 1998The latest roll call mentions ""Gus, who guy who owns property onstage"" and ...
72. Charles Grodin, John Witherspoon, Jessye Norman
Aired: Dec 22, 1998Dave refunds $50 to an audience lady with a Late Show sweatshirt; a Joe G's c...
73. John Travolta, Darlene Love
Aired: Dec 23, 1998Soon-to-be-traded Yankees pitcher David Wells sits in the audience; the first...
74. Chazz Palminteri, Ann Curry, Rufus Wainwright
Aired: Dec 28, 1998Dave 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, 1998Bisbee, North Dakota is investigated in the latest edition of ""Biff Henderso...
76. Jay Thomas, Vinny Testaverde, Patti Smith
Aired: Dec 30, 1998Throughout 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, 1998Kamarr the Discount Magician makes one last appearance.
78. Jon Voight, Jena Malone, Louie C.K.
Aired: Jan 1, 1999Jon Voight promotes two films, ""Enemy of the State"" and ""Varsity Blues.""
79. Sarah Jessica Parker, David Remnick, Bryan Callan
Aired: Jan 4, 1999Biff pretends to stand in Times Square again, this time reporting about the w...
80. Jennifer Jason Leigh, Liam Aiken, Greg Behrendt
Aired: Jan 5, 1999Biff just can't get enough of the green screen in the hallway; tonight's part...
81. Mira Sorvino, Terry Bradshaw
Aired: Jan 6, 1999It'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, 1999Dave 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, 1999Sitting in with the CBS Orchestra tonight: the shirtless guy who was the ""T"...
85. Robert Duvall, Al Franken, B.B. King
Aired: Jan 12, 1999During ""Small Town News,"" Dave sports a paper mustache.
86. Conan O'Brian, Alanis Morrisette
Aired: Jan 13, 1999Tonight's ""Paul Shaffer Millennium Prediction"": health spas will not charge...
87. William Baldwin, Trisha Yearwood, Scott Ferrall
Aired: Jan 14, 1999William Baldwin promotes ""Virus,"" while Biff rescues Dave's coffee mug afte...
88. Jack Hanna, Patricia Arquette
Aired: Jan 15, 1999Mailbag: Tony mentions he's taken up acting, then shows two remarkably simila...
89. Yasmine Bleeth, Adam Carolla, James Brown
Aired: Jan 25, 199990. Alicia Silverstone, D.L. Hughley, Second Hand
Aired: Jan 26, 1999Dave says a focus group doesn't like his ""Countdown to the Millennium"" segm...
91. Sophia Loren, The Mavericks
Aired: Jan 27, 1999Dave and Paul discuss William Wood Lee Shaffer's diapers. Later, Paul interr...
92. Bill Murray, Shania Twain
Aired: Jan 28, 1999Biff shows up with a tie for a ""Know Your Current Events"" contestant; Bill ...
93. Cate Blanchett, Jason Schwartzman, Brandy
Aired: Jan 29, 1999Dave 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, 1999It'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, 1999Dave mentions that through the wonders of science, Paul Shaffer had another b...
96. Tom Brokaw, Sean Patrick Flanery, Creed
Aired: Feb 3, 1999Dave and Paul spend ten minutes discussing the new and improved ""Late Show""...
97. Mel Gibson, Laetitia Casta, Fresh Step
Aired: Feb 4, 1999Dave reads about Bucknell University for a ""KYCE"" participant; Laetitia Cas...
98. Stupid Pet Tricks, Martha Stewart, Mitch Hedberg
Aired: Feb 5, 1999Nile 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, 1999Dave chats with (live via satellite) Al at Prestige Luggage Company in Dallas...
101. Robin Wright Penn, Richard Kind, Chris Isaak
Aired: Feb 10, 1999Dave rants about the internet, while Bob Borden literally searches for a vale...
102. Sandra Bullock, James Carville, Hootie & The Blowfish
Aired: Feb 11, 1999Orlando Antigua of the Harlem Globetrotters helps out during ""Know Your Curr...
103. Richard Simmons, Sarah O'Hare, Ondar
Aired: Feb 12, 1999Dave discusses signature sign-offs and announces his new one will be ""Keep a...
104. Bette Midler, David Hyde Pierce
Aired: Feb 15, 1999Tonight marks the debut of ""Alan Kalter's Secret Word."" Tonight's utteranc...
105. Andy Garcia, Tara Lipinksi, Wendy Liebman
Aired: Feb 16, 1999Lou 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, 1999The secret word is ""mongoose""; ten West Point cadet presents the Top Ten; J...
107. Magic Johnson, Jake Gyllenhaal, Jewel
Aired: Feb 18, 1999The secret word is ""hydraulic""; Dave gives a photographer in the audience a...
108. Lauren Bacall, Greg Smith, Sugar Ray
Aired: Feb 19, 1999The secret word is ""buttress""; during Mailbag, Dave and Linda Tripp appear ...
109. Matthew Broderick, Sheryl Crow
Aired: Feb 22, 1999Dave takes five minutes to comment on the sudden death of Gene Siskel, then s...
110. Kid Scientists, Jesse Ventura
Aired: Feb 23, 1999Alan's secret word is ""bobcat,"" and the jackpot now stands at ""seven hundr...
111. Uma Thurman, Tom Green, De La Guarda
Aired: Feb 24, 1999The secret word is ""barnacle;"" Dave answers a phone call from Sweden; in a ...
112. Eriq La Salle, Homer Hickman, Blondie
Aired: Feb 25, 1999The secret word is ""corpuscular."" Meanwhile, Dave chats with Homer Hickam, ...
113. James Coburn, Will Ferrall, Marvelous Three
Aired: Feb 26, 1999The secret word is ""combustible,"" and the stakes have been raised to an eve...
114. Brooke Shields, Peter Hillary
Aired: Mar 1, 1999115. Ian McKellen, Reese Witherspoon, The Roots & Erykah Badu
Aired: Mar 2, 1999The secret word is ""saluki""; live via satellite, the employees of the Uncla...
116. Kid Turkey Callers, Mark Wahlberg, Fresh Step
Aired: Mar 3, 1999Dave rants about tonight's Barbara Walters/Monica Lewinsky interview; the sec...
117. Billy Crystal, George Miller
Aired: Mar 4, 1999The secret word is ""viscous,"" while George Miller rants about the media.
118. Chazz Palminteri, Jeff Altman, Everclear
Aired: Mar 5, 1999The secret word is ""melancholia,"" while ""Oprah"" (Pat Farmer) flirts with ...
119. Norm MacDonald, Jeff Beck
Aired: Mar 22, 1999The secret word is ""lederhosen""; the second-ever ""Alan Kalter's Where Are ...
120. Elizabeth Hurley, Katie Holmes, Cake
Aired: Mar 23, 1999The 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, 1999The secret word is ""shipjack""; Dave shows a meat identification kit, comple...
122. Elton John, Henry Kissinger, LeAnn Rimes
Aired: Mar 25, 1999The secret word is ""bilious,"" which is coincidental because Dave feels unde...
123. Ron Howard, Charlotte Church
Aired: Mar 26, 1999Dave bids farewell to Tom Snyder (his last show aired that night),then says ...
124. Marv Albert, Diane Lane, Blur
Aired: Mar 29, 1999Dave hollers about 60 Minutes, then claims that somebody won the Secret Word ...
125. Laurence Fishburne, Sister Carol Anne Corley, Wilco
Aired: Mar 30, 1999The opening sequence is altered; the secret word is ""taconite""; Dave chats ...
126. Steve Martin & Goldie Hawn, Jim Calhoun, Joe Henry
Aired: Mar 31, 1999The secret word is ""sociopathic,"" while Steve Martin and Goldie Hawn promot...
127. Dennis Hopper, Jason Nastke, The Corrs
Aired: Apr 1, 1999The secret word is ""nemonurwingy,"" but Dave accuses Alan of making it up (w...
128. Marilu Henner, Master P, Greg Fitzsimmons
Aired: Apr 2, 1999Charlie 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, 1999The secret word is ""flange""; Dave holds up a certificate that makes Late Sh...
130. Drew Barrymore, Scott Wolf, Barenaked Ladies
Aired: Apr 6, 1999The secret word is ""millipede""; right after the second-ever edition of ""Kn...
131. Lennox Lewis, Dr. Bertrand Piccard & Brian Jones
Aired: Apr 7, 1999Throughout the night, local teens with learner's permits parallel park on 53r...
132. George Stephanopoulos, Molly Shannon, Andrea Bocelli
Aired: Apr 8, 1999The secret word is ""ischemia,"" while SNL star Molly Shannon promotes Never ...
133. Bill Maher, Khalid El-Amin, Marc Maron
Aired: Apr 9, 1999Paul makes his second ""Countdown to the Millennium"" prediction since the de...
134. Elle Macpherson, Don Zimmer, John Mellencamp
Aired: Apr 12, 1999Paul announces celebrities will come by all evening to wish Dave a happy birt...
135. Kevin Spacey, Tom Petty & The Heartbreakers
Aired: Apr 13, 1999The secret word is ""hegemony,"" and Dave doubles the current jackpot from $1...
136. Kate Winslet, Darrell Hammond, Mandy Barnett
Aired: Apr 14, 1999The secret word is ""quadricentennial,"" and after doubling the stakes on las...
137. David Spade, Tim Couch, Eagle-Eye Cherry
Aired: Apr 15, 1999Dave mentions the sudden and untimely death of Bill Wendell; the secret word ...
138. John Cusack, Jack Hanna
Aired: Apr 16, 1999A technical difficulty turns Dave's face and tie blue during the monologue; t...
139. Matthew Broderick, Ben Stein, The Cranberries
Aired: Apr 26, 1999Dave discusses the various bars and/or grills that have been next door to the...
140. Martin Lawrence, Michelle Williams, Eddie Brill
Aired: Apr 27, 1999Dave claims there was a secret word winner last night, then brings out Connec...
141. Dustin Hoffman, Mary Steenburgen, Ben Folds Five
Aired: Apr 28, 1999The secret word is ""boat""; Paul, Felecia, Will, and Sid perform ""Songs for...
142. Ted Danson, Sarah Ferguson, Madness
Aired: Apr 29, 1999The secret word is ""carrot,"" and Dave introduces another supposed winner (w...
143. Glenn Close, George Hamilton, Elvis Crespo
Aired: Apr 30, 1999In honor of tonight's audience, the backdrop is altered to show the skyline o...
144. Tom Brokaw, Robbie Williams
Aired: May 3, 1999Dave claims he's filed a $100 million lawsuit against the surgeon general; Da...
145. Earvin Magic Johnson, Sara Gentile, Silverchair
Aired: May 4, 1999The secret word is ""incinerate""; Paul Fiore tries to parallel-park outside;...
146. Denny Brauer, Kelly Willis, Jesse Jackson
Aired: May 5, 1999The secret word is ""undershirt""; Dave shows (bogus) footage of Roberto Beni...
147. Brendan Fraser, Jesse Jackson, Bonnie Raitt
Aired: May 6, 1999Cold 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, 1999In honor of tonight's travel-weary audience (everybody's from Nashville),Bif...
149. Stupid Pet Tricks, Janeane Garofalo, Brian Regan
Aired: May 10, 1999The secret word is ""ball""; an audience member is stifled by a barbershop qu...
150. Ben Stiller, Camryn Manheim, Eve 6
Aired: May 11, 1999Thirteen-year-old blues phenomenon Ben Robinson sits in; the secret word is "...
151. Kathie Lee Gifford, Deana Carter
Aired: May 12, 1999Dave makes a nonsense rant about Barry Manilow; the secret word is ""winky"";...
152. Kevin Kline, Leelee Sobieski, Beth Orton
Aired: May 13, 1999Dave bring out the seven supposed winners of last night's secret word contest...
153. Bill Cosby, Jon Favreau
Aired: May 14, 1999With tonight's audience being from the City of Brotherly Love, Biff heads to ...
154. Julia Roberts, Alice Cooper
Aired: May 17, 1999The secret word is ""molar,"" while Dave measures Julia Roberts' waist.
155. Keri Russell, Aretha Franklin
Aired: May 18, 1999Dave calls Aloha Meats in Honolulu to see if they answer the phone by saying ...
156. Tom Selleck, Bob Barker, Leon Russell
Aired: May 19, 1999The secret word is ""turf""; various members of the staff appear in a series ...
157. Helen Hunt, Courtney Love, Hole
Aired: May 20, 1999The 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, 1999Tonight's audience hails from Boston, Massachusetts. The backdrop, as always...
159. Harry Connick Jr., Damon Wayans
Aired: May 24, 1999Dave goes on a fury as to what constitutes the dinners given as prizes during...
160. Kate Capshaw, Britney Spears
Aired: May 25, 1999Dave tries calling Hawaii again; the secret word is ""asparagus""; Kate Capsh...
161. Kid Scientists, Sarah Jessica Parker, Mary Chapin Carpenter
Aired: May 26, 1999Anton is again introduced as Buddy Rich, Jr.; Paul pays $102,000,000 for a ti...
162. Bill Murray, Everlast
Aired: May 27, 1999Jay Johnson wins the secret word ""contest"" again; throughout the night, Lou...
163. Jennifer Lopez, Ira Glass
Aired: May 28, 1999The secret word is ""bituminous""; Lou Rawls continues to lounge in the green...
164. Dan Rather, Nancy Mace, Randy Newman
Aired: Jun 7, 1999Tonight's secret word (""emetic"") is now sponsored by a lawn-watering device...
165. Jeff Foxworthy, Kristin Davis, Snoop Dogg
Aired: Jun 8, 1999The 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, 1999The Hosie Cow Secret Word is ""whippy""; last night's winner ""Barbara Sanche...
167. Ray Romano, Jewel
Aired: Jun 10, 1999After appearing in an ad for Hosie Cow, Alan announces that the secret word i...
168. Heather Graham, David Wells
Aired: Jun 11, 1999Edgar 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, 1999The Hosie Cow Secret Word is ""amputation""; the latest roll call introduces ...
170. Roseanne, Susan Tedeschi
Aired: Jun 15, 1999The Hosie Cow Secret Word is ""dick"" again, but it's eventually changed to "...
171. David Schwimmer, Brandi Chastain, Seth Green
Aired: Jun 16, 1999The Hosie Cow Secret Word is ""pigment,"" while Dave chats (and becomes infat...
172. Mike Myers, Ben Lee
Aired: Jun 17, 1999Al Gore appears on ""The Paul Shaffer Show""; The Hosie Cow Secret Word is ""...
173. Julianna Margulies, Jon Stewart
Aired: Jun 18, 1999Anton is introduced as Buddy Rich Jr., the ""bastard son"" of the legendary j...
174. Felicity Huffman, Andy Dick, Elvis Costello
Aired: Jun 21, 1999The secret word (""rodeo"") is now sponsored by Larry King, whom according to...
175. Adam Sandler, Missy Elliot
Aired: Jun 22, 1999The Larry King Secret Word is ""gabardine,"" and is followed by stock footage...
176. Geri Halliwell, Richard Belzer
Aired: Jun 23, 1999Jimmy Vaughan sits in; the Larry King Secret Word is ""entropic""; after an u...
177. Rudolph Giuliani, Leslie Mann, The Pretenders
Aired: Jun 24, 1999The Larry King Secret Word is ""linguine."" Also, to counteract with Hillary...
178. Joey Lauren Adams, Spike Lee, Santana
Aired: Jun 25, 1999The Larry King Secret Word is ""peptide""; Carlos Santana and Rob Thomas of M...
179. Colin Powell, Maurice Green
Aired: Jun 28, 1999Tonight's Secret Word (""bird"") is brought to you by David Letterman's Women...
180. Mira Sorvino, Lyle Lovett
Aired: Jun 29, 1999The World Cup Soccer Team Secret Word is ""oozing""; Montana park ranger (and...
181. Piedmont Bird Callers, Avery Johnson, June Carter Cash
Aired: Jun 30, 1999The Larry King/Women's Soccer Secret Word is ""peripatetic""; a bird caller f...
182. Calista Flockhart, Jack Hannah
Aired: Jul 1, 1999The Larry King/Women's Soccer Secret Word is ""highoeyazmuhoodhee""; Calista ...
183. Stupid Human Tricks, John Leguizamo, Ziggy Marley & The Melody Makers
Aired: Jul 2, 1999The Larry King/Women's Soccer Secret Word is ""pony""; during Mailbag, Biff, ...
184. John McEnroe, George Jones
Aired: Jul 5, 1999Dave shows footage of a taxi literally crashing the staff cookout out on 53rd...
185. Chris Rock, Sixpence None the Richer
Aired: Jul 6, 1999An audience member attempts to button Dave's jacket; the Dan Quayle/Larry Kin...
186. Lindsay Davenport, Oliver Platt, Jeffrey Ross
Aired: Jul 7, 1999Dave replies to a Zagat's survey; the Women's Soccer Secret Word is ""pestile...
187. Jay Thomas, Jason Briggs
Aired: Jul 8, 1999The Secret Word is ""prick,"" with the stock footage of the baby owls eating ...
188. Naomi Campbell, Jimmie Walker, Lucinda Williams
Aired: Jul 9, 1999Dave points out that Paul is dressed from head to toe in white tonight, inclu...
189. Don Rickles, Dave Mirra, Patty Griffin
Aired: Jul 19, 1999The 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, 1999The Dan Quayle/Larry King Secret Word is ""pie""; Dave finally meets the enti...
191. Matthew Broderick, Dennis Regan
Aired: Jul 21, 1999The Hillary Clinton/Larry King Secret Word is ""mommy""; Dave asks a question...
192. Catherine Zeta-Jones, Buzz Aldrin, Jamiroquai
Aired: Jul 22, 1999The Hillary Clinton/Larry King Secret Word is ""meehnkee""; Dave ""performs""...
193. Charles Grodin, Alanis Morrisette
Aired: Jul 23, 1999Paul 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, 1999Paul complains about the heat at Woodstock '99; Dave brags about Max Pappas a...
195. National Hollerin' Champions, Garry Marshall, Los Lobos
Aired: Jul 27, 1999Buckwheat Zydeco (nee Stanley Durrell) sits in on accordion; throughout the n...
196. Samuel L. Jackson, Rita Wilson, Pete Townshend & Eddie Vedder
Aired: Jul 28, 1999Biff 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, 1999Dave chats with Tour de France winner and cancer survivor Lance Armstrong; Pa...
199. Pierce Brosnan, Saffron Burrows, Jim Jeter
Aired: Aug 2, 1999It'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, 1999Dave 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, 1999Dave 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, 1999Dave repeatedly shows footage of the Taco Bell chihuahua saying ""funkaliciou...
203. Ray Romano, Jeff Altman
Aired: Aug 6, 1999During CBS Mailbag, Alan punches Dave. Later, Dave's former ""Starland Vocal...
204. Regis Philbin, Dave Attell
Aired: Aug 9, 1999Paul refers to Regis as a bastard, only for the ""Millionaire"" host to retal...
205. Claire Danes, Smash Mouth
Aired: Aug 10, 1999Kreskin's knowledge of 70's backup singers is tested in a segment called ""Co...
206. Hugh Grant, The Mavericks
Aired: Aug 11, 1999Dave announces that a crack in the building next door caused a temporary evac...
207. Rene Russo, Tori Amos
Aired: Aug 12, 1999Dave takes up an offering for a preacher who played ""Who Your Deer Repellant...
208. Shaquille O'Neal, Helen Mirren
Aired: Aug 13, 1999During CBS Mailbag, Inky Mendez announces his candidacy for the US Senate, wh...
209. Tony Danza, Katie Holmes, Robert Palmer
Aired: Aug 16, 1999A shirtless Vince DeMentri interviews people on the street, asking them what ...
210. Lara Flynn Boyle, David Brenner, Everclear
Aired: Aug 17, 1999Dave announces that tonight, ""We're going to have good old-fashioned fun"": ...
211. Andie MacDowell, French Stewart, Tom Dreesen
Aired: Aug 18, 1999Terence Blanchard sits in with the band, while Olympic diver Kathy Pesek does...
212. Alec Baldwin, Dwight Yoakam
Aired: Aug 19, 1999Dave announces that tonight is the premiere of ""Late Show Who Wants to be a ...
213. Albert Brooks, Omar Epps
Aired: Aug 20, 1999Dave announces that after 6 years and 1,278 shows on CBS, he now wants to be ...
