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Season guide

Late Show with David Letterman: Season 6

213 episodes Premiered Aug 31, 1998 Updated Sep 25, 2026
Previously on Late Show with David Letterman

Season 6 Lore Primer

Key plot threads, lore context, and character stakes you need to remember before diving into this season.

  • ⚡ Directly follows the overarching narrative developments of Late Show with David Letterman Season 5.
  • ⚡ Faction dynamics and core character alliances shift under escalating external stakes.
  • ⚡ Crucial mysteries introduced previously reach key turning points and narrative reckonings.
  • ⚡ Sets up serialized story arcs that build directly toward the climactic season finale.
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Season 6 Episodes

Episode Guide

🛡️ SPOILER SHIELD

Season 6 Progress Shield

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Binge Efficiency Engine

Season 6: Filler vs. Essential Canon

Filter episodes by narrative weight. Focus on essential mytharc and skip standalone side quests.

98%
Mytharc (5): Crucial lore & season climaxes
Core (208): Character development & subplots
Side Quest (0): Standalone / filler
S6·E2 Core

Beau Bridges, Terrell Davis, Squirrel Nut Zippers

Sep 1, 1998

Dave points out that the show has undergone budget cuts, which might explain the tiny cue cards Tony's holding. Later, Beau Bridges promotes his new series, ""Maximum Bob.""

S6·E3 Core

Terry Bradshaw, Jesse Jackson

Sep 2, 1998

Dave makes a lenghty rant about ""The Late Shift"" after an audience member asks him for an autograph; Martin Short sings the Top Ten List; Terry Bradshaw makes his predictions for

S6·E4 Core

Ray Romano, Chris Cardone, Tom Agna

Sep 3, 1998

Alan Kalter comments on home run record that is being chased by Mark McGwire; Dave announces that CBS ""just don't care 'bout"" the new fall lineup; Ray Romano talks about his fami

S6·E8 Core

Tim Forneris, Stephen Dorff, Wynonna

Sep 9, 1998

Dave goes on a tirade about the CBS watermark on the lower right hand side of the screen. Later, Dave chats with the guy who caught Mark McGwire's 62nd Home Run ball.

S6·E9 Core

Charles Grodin, Paul Hopkins

Sep 10, 1998

Dave stuggles to grow a beard; Charles Grodin promotes his talk show; Dave chats with the former Washington Senators pitcher who gave up Babe Ruth's 59th home run in 1927 (in his M

S6·E12 Core

Ben Stiller, Jackie Chan, Vince Gill

Sep 15, 1998

Dave shows a (bogus) Mastercard ad starring Ken Starr; Biff goes to Chicago for another Home Run Report; Jackie Chan does an great Elvis impression.

S6·E13 Core

Bill Cosby, George Hamilton

Sep 16, 1998

Biff brings in scissors for a tie trim; Calvert impersonates Hank Williams, Jr.; Bill Cosby plays sax under the alias ""Philly Billy Be Bop.""

S6·E14 Core

Denis Leary, George Hamilton

Sep 17, 1998

Dave apologizes for his affair with Angela Lansbury, while Biff apologizes for his affair with Dave's wife. Shortly afterwards, Dorothy calls and insults Dave.

S6·E15 Core

Vince Vaughn, Brian Benben, Brian Setzer Orchestra

Sep 18, 1998

Dave makes another rant pertaining to the CBS Watermark; kid Geography whiz Jonathan Estrada helps out during CBS Mailbag; Brian Benben promotes his new, self-titled (and quickly c

S6·E18 Core

Stupid Pet Tricks, Marv Albert, Kevin James

Sep 23, 1998

A gag promo for the TV series ""Biffy, The Umpire Layer"" is declared the worst joke ever seen on the show; an ""Audience Vote"" determines Rip Taylor as tonight's guest instead of

S6·E19 Core

Howard Stern, Katie Holmes

Sep 24, 1998

Dave makes fun of Inky's summer camp outfit. Later, Howard Stern plays with his gut and strips to his underwear in order to show off his legs.

S6·E22 Core

Chris Tucker, Faith Ford, Eagle Eye Cherry

Sep 29, 1998

Dave lets Inky go on a ""gum break;"" George Clarke is introduced as operator of the Late Show hedge fund; Biff demands more scandals involving President Clinton; Chris Tucker prom

S6·E25 Core

Steve Martin, Cokie Roberts

Oct 2, 1998

During CBS Mailbag, Alan promotes ""Alan Kalter's Music To Make Love By,"" which includes two TV theme songs and a doorbell. Later, Steve Martin's lengthy absence from appearing o

S6·E27 Core

Elizabeth & Bob Dole, Joaquin Phoenix

Oct 6, 1998

Tony Mendez does a ""card trick""; Tito Puente contributes drumrolls to the Top Ten list; Dave shows a (bogus) new, improved $20 bill.

S6·E28 Mytharc

Jeff Goldblum, John Mellencamp

Oct 7, 1998

A new segment called ""This Day in Late Show History"" reveals that October 7 was a Saturday in 1994. Biff corrects Dave, telling him it was a Friday. Later, Jeff Goldblum promot

S6·E30 Core

Joan Lunden, Jeff Altman, Sheryl Crow

Oct 9, 1998

During CBS Mailbag, Tony bares his ass again, and The Foul-Mouthed Scenic Designer (Kathleen Ankers) lives up to her title.

S6·E31 Core

Mark McGwire, Robert Benigni, Bruce Hornsby

Oct 19, 1998

The calvacade of mediocre crops continues as ""Joe Whitworth"" from Oregon walks onstage with a ""gigantic"" pumpkin; Biff presents a World Series Report despite a sore throat; Rob

S6·E32 Core

State Fair Champions, Ringo Starr

Oct 20, 1998

It's Dave's 3000th show in late night, so he celebrates by bringing Charles Grodin onstage to break the monotony of chatting with Paul. Later, Dave introduces some State Fair winn

S6·E34 Core

Danny Glover, Cal Ripken Jr., R.E.M.

Oct 22, 1998

Biff participates in more interviews in part two of his World Series report, while Danny Glover plugs ""Lethal Weapon 4.""

S6·E35 Core

Naomi Campbell, David Wells, R.E.M.

Oct 23, 1998

Tony's eye itches, and Dave gives him a hard time for potentially screwing up the cue cards; during CBS Mailbag, Dave interrogates TV star ""Calista Flockhart"" (Gerard), who magic

S6·E40 Core

Ted Danson, Denny Brauer, Black Sabbath

Oct 30, 1998

Dave announces the names of staff members who will run in the New York City Marathon; Biff gives out candy to the audience; Dave shows a box of Snoop Doggy Dogg dog biscuits, so Da

S6·E41 Core

Anthony Hopkins, Buzz Aldrin, Depeche Mode

Nov 2, 1998

New York Marathon winner John Kagwe runs through during the monologue, and is later followed by women's winner Franca Faicconi. Later, Dave spills coffee on his tie and suffers a

S6·E42 Core

Queen Latifah, Ellie Lammer, Darrell Hammond

Nov 3, 1998

Dave gives bogus election results; the outside cam goes to Joe G's for another round of ""Please Stop Calling Me Debbie""; Dave chats with Ellie Lammer, a 12-year-old who examined

S6·E43 Core

Adam Sandler, Jayson Williams, Soul Coughing

Nov 4, 1998

Dave shows a clip of new Minnesota governor Jesse ""The Body"" Ventura in the movie ""The Running Man""; Senator Chuck Schumer presents the Top Ten; basketball star (and future all

S6·E44 Core

Denzel Washington, Father Mike Berner

Nov 5, 1998

Tony gets scolded for chewing gum; shortly after appearing on ""Know Your Current Events,"" an audience member starts singing; Dave interviews a Catholic priest that won the Publis

S6·E46 Core

George Michael, Col. Gail Halverson, Hanson

Nov 9, 1998

Dave mentions that Meryl Streep, tonight's scheduled guest and star of the movie ""One True Thing,"" had to cancel at the last minute. In place of the Oscar-winner is Retired Col.

S6·E49 Core

Roma Downey, Kenneth Branagh, Goo Goo Dolls

Nov 12, 1998

Dave accuses Tony Mendez of goosing someone with a cue card; Roma Downey and Kenneth Branagh meet for the first time; Pat and Kenny sing the theme song to ""Pat and Kenny Read Opra

S6·E51 Core

Kid Scientists, Cameron Diaz, Mariah Carey

Nov 16, 1998

Jayson Williams of the New Jersey Nets operates one of the cameras; a ""Kid Scientist"" from Naperville, Illinois cracks eggs; Cameron Diaz plugs ""Very Bad Things.""

S6·E52 Core

Will Smith, Jack Hanna

Nov 17, 1998

Dave once again takes away Tony's gum, while Paul tries to flirt with Monica Lewinsky and Linda Tripp.

S6·E55 Core

Drew Barrymore, Siskel & Ebert

Nov 20, 1998

Todd Rundgren sits in, while Drew Barrymore walks onstage so that she can show what her new dog looks like.

S6·E56 Core

Helen Hunt, Ray Romano

Nov 23, 1998

James Cotton sits in; Dave discusses Dr. Kevorkian and the safest handling of a Thanksgiving turkey; the 5th anniversary special (which aired that night) is spoofed.

S6·E57 Core

Geena Davis, Martha Stewart, Roger Daltrey

Nov 24, 1998

As he does almost every Thankgiving, Kreskin plays for pride in a little game called ""White Meat / Dark Meat."" Tonight, he correctly guesses that Dennis Franz (live via telephon

S6·E58 Core

Gwyneth Paltrow, Peter Berg, Bonnie Raitt

Nov 25, 1998

Jayson Williams of the Nets comments on the NBA lockout, then drops phony turkeys out the 4th floor window. Later, Gwyneth Paltrow plugs ‘Shakespeare In Love.""

S6·E59 Core

Michael Caine, Jewel

Nov 26, 1998

Dave warns pedestrians (via his PA system) that the turkey is bad; a guy in the balcony talks to Dave about turning flips onstage; Paul correctly guesses that Dorothy baked a rhuba

S6·E61 Core

Patrick Stewart, Jon Stewart, Faith Hill

Dec 7, 1998

It's ""Stewart Night,"" as all the guests share the same last name despite not being related. French Stewart chats with Dave via telephone, Calvert does his famous Rod Stewart imp

S6·E62 Core

Greg Kinnear, Jane Horrocks, Reggie McFadden

Dec 8, 1998

Live from Times Square, it's ""Dick Clark's Rockin' December 9 Countdown."" At the stroke of midnight, Greg Kinnear commutes from the theater to give Dick a kiss.

S6·E63 Core

Tom Hanks, Brooklyn Philharmonic

Dec 9, 1998

Gerard plays an openly gay man in ""Who Asked For It?""; The Brooklyn Philharmonic plays the ""William Tell Overture.""

S6·E64 Core

Meg Ryan, Whitney Houston

Dec 10, 1998

Dave compares an electrician that played ""KYCE"" to John Elway. Also, Meg Ryan plugs ""You've Got Mail.""

S6·E65 Core

Tom Brokaw, Famke Janssen, Emmylou Harris

Dec 11, 1998

Tom Brokaw drops by sporting a turtleneck sweater in lieu of his usual two-piece suit, and pretty soon Biff is handing out turtlenecks to the audience. By the end of the show, eve

S6·E66 Core

Robin Williams, Natalie Merchant

Dec 14, 1998

Dave explains the impeachment process; Robin Williams hosts the PBS special ""The Shaffer Campaign: A Look Back,"" which details Paul's futile attempt to run for congress.

S6·E69 Core

Jeff Goldblum, Angelina Jolie, Third Eye Blind

Dec 17, 1998

Live from sunny Los Angeles, it's ""Dick Clark's Rockin' Countdown to December 18,"" followed by ""Casey Kasem's Countdown to Dick Clark's Rockin' Countdown to December 18."" When

S6·E70 Core

Julia Roberts, David Kelly

Dec 18, 1998

During Mailbag, Alan gives the audience an unusual egg nog recipe, while Dave answers the question, ""Where did Hanukkah come from?"" by stating it that was named after a nice man

S6·E71 Core

Barbara Walters, Josh Hartnett, Cyndi Lauper

Dec 21, 1998

The latest roll call mentions ""Gus, who guy who owns property onstage"" and ""Tony Randall as Ricky, the stagehand who looks like Regis Philbin.""

S6·E72 Core

Charles Grodin, John Witherspoon, Jessye Norman

Dec 22, 1998

Dave refunds $50 to an audience lady with a Late Show sweatshirt; a Joe G's customer appears in the hastily-produced film trailer for the faux movie ""Badge of Honor III""; ten dep

S6·E73 Core

John Travolta, Darlene Love

Dec 23, 1998

Soon-to-be-traded Yankees pitcher David Wells sits in the audience; the first of tonight's two Top Ten Lists is interrupted by a claymation segment with Dave and Santa; Cissy Houst

S6·E74 Core

Chazz Palminteri, Ann Curry, Rufus Wainwright

Dec 28, 1998

Dave talks about the recent successes of the New York Jets, so Harold Larkin goes outside to alter the ""Jets Suck"" graffiti on the wall; Biff keeps changing sweatshirts; ten beau

S6·E76 Core

Jay Thomas, Vinny Testaverde, Patti Smith

Dec 30, 1998

Throughout the night, Chicago announcer ""Ray Clay"" fills in for Alan, making inane announcements and usurping the Top Ten from Dave. Also, a Late Show tradition is born when Jay

S6·E80 Core

Jennifer Jason Leigh, Liam Aiken, Greg Behrendt

Jan 5, 1999

Biff just can't get enough of the green screen in the hallway; tonight's participant in ""Please Stop Calling Me Monty"" jams with the band; Dave chats with child actor Liam Aiken.

S6·E81 Core

Mira Sorvino, Terry Bradshaw

Jan 6, 1999

It's time for ""How Many Guys in Mouse Suits Can Fit into a Dunkin' Donuts?"" We never find out the exact number, though they do bring back doughnuts.

S6·E82 Core

Lisa Kudrow, Terry Bradshaw, Jason Kuller

Jan 7, 1999

Dave announces the new name of the show will be ""David Letterman's Countdown to the Millennium."" Also, the show profiles audience member ""Spencer Alderson"" (Leonard) of Sweden

S6·E83 Core

Jon Stewart, Marv Albert, Jim Gaffigan

Jan 8, 1999

""David Letterman's Countdown to the Millennium,"" Day 2: Paul declares that he will mention a millennium-related fun fact every day for the rest of the year. Also, Jon Stewart pr

S6·E84 Core

Gillian Anderson, Charlie Rose, Black Crowes

Jan 11, 1999

Sitting in with the CBS Orchestra tonight: the shirtless guy who was the ""T"" in ""Jets"" at last night's game. Also, The Black Crowes performs ""By Your Side.""

S6·E86 Core

Conan O'Brian, Alanis Morrisette

Jan 13, 1999

Tonight's ""Paul Shaffer Millennium Prediction"": health spas will not charge deposits. Upon hearing this, Dave wishes people would stop using the phrase ""happy camper."" Also,

S6·E88 Core

Jack Hanna, Patricia Arquette

Jan 15, 1999

Mailbag: Tony mentions he's taken up acting, then shows two remarkably similar clips from Patch Adams and Shakespeare In Love. Also, NBA head honcho David Stern presents the Top T

S6·E90 Core

Alicia Silverstone, D.L. Hughley, Second Hand

Jan 26, 1999

Dave says a focus group doesn't like his ""Countdown to the Millennium"" segment, so Paul gives one last fact: ""Danny Aiello will get another series."" Rather than bow down in de

S6·E91 Core

Sophia Loren, The Mavericks

Jan 27, 1999

Dave and Paul discuss William Wood Lee Shaffer's diapers. Later, Paul interrupts the ""Shark Week"" segment with another Millennium prediction: ""The new black… will be black.""

S6·E92 Core

Bill Murray, Shania Twain

Jan 28, 1999

Biff shows up with a tie for a ""Know Your Current Events"" contestant; Bill Murray promotes Rushmore and serenades Dave.

S6·E93 Core

Cate Blanchett, Jason Schwartzman, Brandy

Jan 29, 1999

Dave announces he and Paul are trying to establish a video nexus; during Mailibag, Anton falls down an elevator shaft, while Paul and Dave shoot Regis with paintballs; ten firefigh

S6·E95 Core

Tom Arnold, David Brenner, Catherine Bell

Feb 2, 1999

Dave mentions that through the wonders of science, Paul Shaffer had another baby over the weekend, and then introduces Bernard Shaffer in the green room; during ""Who Asked For It?

S6·E96 Core

Tom Brokaw, Sean Patrick Flanery, Creed

Feb 3, 1999

Dave and Paul spend ten minutes discussing the new and improved ""Late Show"" home site; Dave chats with ""John Elway"" (Gerard) after the star quarterback is last minute no-show;

S6·E100 Core

Jeff Daniels, Fernanda Montenegro, Monica

Feb 9, 1999

Dave chats with (live via satellite) Al at Prestige Luggage Company in Dallas. Dave is so fascinated by him that the segment runs for almost fifteen minutes, and later Al presents

S6·E103 Core

Richard Simmons, Sarah O'Hare, Ondar

Feb 12, 1999

Dave discusses signature sign-offs and announces his new one will be ""Keep a light coat of oil on it""; during Mailbag, Gerard discusses nudity in film and gets distracted by his

S6·E104 Core

Bette Midler, David Hyde Pierce

Feb 15, 1999

Tonight marks the debut of ""Alan Kalter's Secret Word."" Tonight's utterance: ""gristle."" Also, racing star Jeff Gordon presents the Top Ten, while Dave gives the blue cards fo

S6·E105 Core

Andy Garcia, Tara Lipinksi, Wendy Liebman

Feb 16, 1999

Lou Soloff of Blood, Sweat and Tears sits in with the horn section; Alan's secret word is ""magnesium""; Dave chats with champion figure skater Tara Lipinski.

S6·E107 Core

Magic Johnson, Jake Gyllenhaal, Jewel

Feb 18, 1999

The secret word is ""hydraulic""; Dave gives a photographer in the audience a Polaroid to shoot pictures during the show; Jake Gyllenhaal plugs October Sky.

S6·E108 Core

Lauren Bacall, Greg Smith, Sugar Ray

Feb 19, 1999

The secret word is ""buttress""; during Mailbag, Dave and Linda Tripp appear on $25,000 Pyramid; ten hot dog vendors present the Top Ten.

S6·E109 Core

Matthew Broderick, Sheryl Crow

Feb 22, 1999

Dave takes five minutes to comment on the sudden death of Gene Siskel, then shows a clip from his last appearance on the show; Alan interrupts to show everybody his gritty new 10-1

S6·E110 Core

Kid Scientists, Jesse Ventura

Feb 23, 1999

Alan's secret word is ""bobcat,"" and the jackpot now stands at ""seven hundred damn dollars!"" Also, Kreskin participates in a new game called ""North Dakota/South Dakota,"" wher

S6·E111 Core

Uma Thurman, Tom Green, De La Guarda

Feb 24, 1999

The secret word is ""barnacle;"" Dave answers a phone call from Sweden; in a segment about the hype surrounding Star Wars Episode One, George Clarke impersonates Mark Hamill.

S6·E112 Core

Eriq La Salle, Homer Hickman, Blondie

Feb 25, 1999

The secret word is ""corpuscular."" Meanwhile, Dave chats with Homer Hickam, the NASA shuttle instructor whose life inspired the recent film October Sky.

S6·E113 Core

James Coburn, Will Ferrall, Marvelous Three

Feb 26, 1999

The secret word is ""combustible,"" and the stakes have been raised to an even thousand; during Mailbag, Harold Larkin starts bleeding from the neck, which happens to be a common s

S6·E116 Core

Kid Turkey Callers, Mark Wahlberg, Fresh Step

Mar 3, 1999

Dave rants about tonight's Barbara Walters/Monica Lewinsky interview; the secret word is ""luggage,"" with the grand prize reaching $1300; the latest roll call singles out Tom Crui

S6·E119 Mytharc

Norm MacDonald, Jeff Beck

Mar 22, 1999

The secret word is ""lederhosen""; the second-ever ""Alan Kalter's Where Are They Now?"" reveals that Alan Hale, Jr. has been dead for several years now; Don King helps Norm MacDon

S6·E120 Core

Elizabeth Hurley, Katie Holmes, Cake

Mar 23, 1999

The secret word is ""Ionosphere,"" with the prize now standing at ""$1700 damn dollars!"" Meanwhile, Gaines awkwardly interrupts Dave's interview with Elizabeth Hurley to answer a

S6·E122 Core

Elton John, Henry Kissinger, LeAnn Rimes

Mar 25, 1999

The secret word is ""bilious,"" which is coincidental because Dave feels under the weather. Also, Elton John and Leann Rimes perform ""Written in the Stars.""

S6·E123 Core

Ron Howard, Charlotte Church

Mar 26, 1999

Dave bids farewell to Tom Snyder (his last show aired that night), then says get well to Johnny Carson (who had major surgery). Also, the secret word is ""elliptical.""

S6·E124 Core

Marv Albert, Diane Lane, Blur

Mar 29, 1999

Dave hollers about 60 Minutes, then claims that somebody won the Secret Word ""contest"" on Friday; tonight's Secret Word is ""meniscus,"" with the jackpot reduced to a hundred dol

S6·E127 Core

Dennis Hopper, Jason Nastke, The Corrs

Apr 1, 1999

The secret word is ""nemonurwingy,"" but Dave accuses Alan of making it up (which he did), so he changes it to ""balloon."" Also, after The Corrs perform, Dave decides that ""Corr

S6·E130 Core

Drew Barrymore, Scott Wolf, Barenaked Ladies

Apr 6, 1999

The secret word is ""millipede""; right after the second-ever edition of ""Know Your Cuts of Meat,"" Dave calls one of the previous owners of his Meat Identification Kit.

S6·E131 Core

Lennox Lewis, Dr. Bertrand Piccard & Brian Jones

Apr 7, 1999

Throughout the night, local teens with learner's permits parallel park on 53rd Street. At the end of the show, Dave attempts parallel parking and nearly embarrasses himself.

S6·E133 Core

Bill Maher, Khalid El-Amin, Marc Maron

Apr 9, 1999

Paul makes his second ""Countdown to the Millennium"" prediction since the designation: ""Everybody's going to take out a lot of cash. Forget about the cash."" Also, Dave calls Ja

S6·E134 Core

Elle Macpherson, Don Zimmer, John Mellencamp

Apr 12, 1999

Paul announces celebrities will come by all evening to wish Dave a happy birthday, and for some strange reason Martha Stewart drops by three times; the secret word is ""diplopia"";

S6·E135 Core

Kevin Spacey, Tom Petty & The Heartbreakers

Apr 13, 1999

The secret word is ""hegemony,"" and Dave doubles the current jackpot from $1100 to $2200; Kathie Lee Gifford sings Dave a late happy birthday song, and later he shows a clip of he

S6·E136 Core

Kate Winslet, Darrell Hammond, Mandy Barnett

Apr 14, 1999

The secret word is ""quadricentennial,"" and after doubling the stakes on last night's show, Dave ""raises"" them to an even hundred million; on a variation of a recurring bit, Bif

S6·E137 Core

David Spade, Tim Couch, Eagle-Eye Cherry

Apr 15, 1999

Dave mentions the sudden and untimely death of Bill Wendell; the secret word is ""Melon""; with no clip available, Biff and David Spade reenact a scene from his new movie Lost & Fo

S6·E138 Core

John Cusack, Jack Hanna

Apr 16, 1999

A technical difficulty turns Dave's face and tie blue during the monologue; the secret word is ""tubular""; during Mailbag, Dave shows us the video guide ""Biff Henderson's How to

S6·E139 Core

Matthew Broderick, Ben Stein, The Cranberries

Apr 26, 1999

Dave discusses the various bars and/or grills that have been next door to the theater, and wishes the best of luck to its current incarnation, The Manhattan Chili Company; the secr

S6·E140 Core

Martin Lawrence, Michelle Williams, Eddie Brill

Apr 27, 1999

Dave claims there was a secret word winner last night, then brings out Connecticut housewife ""Marlene DiBenedetto""; the secret word is ""hat,"" with the jackpot going back down t

S6·E141 Core

Dustin Hoffman, Mary Steenburgen, Ben Folds Five

Apr 28, 1999

The secret word is ""boat""; Paul, Felecia, Will, and Sid perform ""Songs for Pedestrians""; Ted Danson lurks in the backdrop during Dave's chat with Mary Steenburgen.

S6·E142 Core

Ted Danson, Sarah Ferguson, Madness

Apr 29, 1999

The secret word is ""carrot,"" and Dave introduces another supposed winner (writer and Boston native Jay Johnson); to prove a point, Dave quizzes Paul on a cut of meat; during a ne

S6·E143 Core

Glenn Close, George Hamilton, Elvis Crespo

Apr 30, 1999

In honor of tonight's audience, the backdrop is altered to show the skyline of Miami, Florida; Biff visits a retirement community in Coral Gables; ten Florida residents present the

S6·E144 Core

Tom Brokaw, Robbie Williams

May 3, 1999

Dave claims he's filed a $100 million lawsuit against the surgeon general; Dave pays an attractive audience member $200 for saying tonight's secret word (""thimble""); Robbie Willi

S6·E145 Core

Earvin Magic Johnson, Sara Gentile, Silverchair

May 4, 1999

The secret word is ""incinerate""; Paul Fiore tries to parallel-park outside; Dave chats with a twelve-year-old girl who wants to save the dying art of ice cream trucks.

S6·E146 Core

Denny Brauer, Kelly Willis, Jesse Jackson

May 5, 1999

The secret word is ""undershirt""; Dave shows (bogus) footage of Roberto Benigni making an ass of himself at the Country Music Awards; World Bass fishing champ Denny Brauer is bump

S6·E147 Core

Brendan Fraser, Jesse Jackson, Bonnie Raitt

May 6, 1999

Cold opening: Jesse Jackson makes an insincere apology to Dave for his tardiness in last night's show. Also, ""Marlene DiBenedetto"" (Jude Brennan) wins the secret word again, and

S6·E148 Core

Kelsey Grammer, Steve Earle and the Del McCoury Band

May 7, 1999

In honor of tonight's travel-weary audience (everybody's from Nashville), Biff hangs out at the Grand Ole Opry while Nashville Predators captain Tom Fitzgerald presents the Top Ten

S6·E149 Core

Stupid Pet Tricks, Janeane Garofalo, Brian Regan

May 10, 1999

The secret word is ""ball""; an audience member is stifled by a barbershop quartet in the latest edition of ""Who Asked For It?""; a dog gets injured during ""Stupid Pet Tricks,""

S6·E150 Core

Ben Stiller, Camryn Manheim, Eve 6

May 11, 1999

Thirteen-year-old blues phenomenon Ben Robinson sits in; the secret word is ""stick""; Bob Borden walks onstage to hype his new catchphrase: ""Next time bring your sister, you hump

S6·E151 Core

Kathie Lee Gifford, Deana Carter

May 12, 1999

Dave makes a nonsense rant about Barry Manilow; the secret word is ""winky""; during ""Dave's Record Collection,"" Tony goes berserk over a comment made by Dave, and he gets thrown

S6·E152 Core

Kevin Kline, Leelee Sobieski, Beth Orton

May 13, 1999

Dave bring out the seven supposed winners of last night's secret word contest (including Mike McIntee and the Stangel brothers); tonight's secret word is ""scooter""; an audience m

S6·E153 Core

Bill Cosby, Jon Favreau

May 14, 1999

With tonight's audience being from the City of Brotherly Love, Biff heads to Philly to get in training a la Rocky. For his efforts, he is given a medal by Philadelphia Mayor Edwar

S6·E155 Core

Keri Russell, Aretha Franklin

May 18, 1999

Dave calls Aloha Meats in Honolulu to see if they answer the phone by saying ""aloha""; the secret word is ""polymer""; Dave and Shecky hang out with a Star Wars fan; Aretha Frankl

S6·E156 Core

Tom Selleck, Bob Barker, Leon Russell

May 19, 1999

The secret word is ""turf""; various members of the staff appear in a series of film promos, including Biff in Eyes Wide Shut; a recently clean-shaven Tom Selleck is treated to a v

S6·E157 Core

Helen Hunt, Courtney Love, Hole

May 20, 1999

The secret word is ""Alan""; Dave shows a one dollar bill folded so it would be shaped like a ring, courtesy of a ""Know Your Current Events"" participant; Helen Hunt promotes the

S6·E158 Core

Natalie Portman, Tom Everett Scott, J. Geils Band

May 21, 1999

Tonight's audience hails from Boston, Massachusetts. The backdrop, as always, is altered to resemble the Beantown skyline; Dave shows various great moments in Red Sox history, sho

S6·E159 Core

Harry Connick Jr., Damon Wayans

May 24, 1999

Dave goes on a fury as to what constitutes the dinners given as prizes during ""Know Your Current Events""; the secret word is ""announcer""; Dave Dorsett doodles on a camera; Tony

S6·E160 Core

Kate Capshaw, Britney Spears

May 25, 1999

Dave tries calling Hawaii again; the secret word is ""asparagus""; Kate Capshaw tries to call her vacationing husband (Steven Spielberg) in Hawaii but she gets a busy signal; Britn

S6·E162 Core

Bill Murray, Everlast

May 27, 1999

Jay Johnson wins the secret word ""contest"" again; throughout the night, Lou Rawls sits in the green room; tonight's secret word is ""litmus""; Everlast performs ""Ends.""

S6·E163 Core

Jennifer Lopez, Ira Glass

May 28, 1999

The secret word is ""bituminous""; Lou Rawls continues to lounge in the green room; during Mailbag, ""Billy Blanks"" (Gerard) gives a rather half-hearted demonstration of Tae-Bo.

S6·E164 Core

Dan Rather, Nancy Mace, Randy Newman

Jun 7, 1999

Tonight's secret word (""emetic"") is now sponsored by a lawn-watering device called ""Hosie Cow""; Biff stands outside holding a popsicle in one hand and a Creamsicle® in the othe

S6·E165 Core

Jeff Foxworthy, Kristin Davis, Snoop Dogg

Jun 8, 1999

The Hosie Cow Secret Word is ""escarpment""; Dave plays a new game at Joe G's where a contestant must start a conversation and brings up the weather within sixty seconds (he won);

S6·E167 Core

Ray Romano, Jewel

Jun 10, 1999

After appearing in an ad for Hosie Cow, Alan announces that the secret word is ""inflammation."" Also, Tony nominee Brian Dennehy presents the Top Ten.

S6·E168 Core

Heather Graham, David Wells

Jun 11, 1999

Edgar Winter sits in; the Hosie Cow Secret Word is ""dick""; Heather Graham promotes Austin Powers: The Spy Who Shagged Me.

S6·E169 Core

Tim Robbins, Oscar De La Hoya, Dane Cook

Jun 14, 1999

The Hosie Cow Secret Word is ""amputation""; the latest roll call introduces Biff's pint-size clone ""Mini-Biff"" and Calvert dressed up as a Hosie Cow; Tim Robbins promotes Arling

S6·E170 Core

Roseanne, Susan Tedeschi

Jun 15, 1999

The Hosie Cow Secret Word is ""dick"" again, but it's eventually changed to ""bunny."" Also, Dave has another one of his long-winded chats (via satellite) with the Preston Luggage

S6·E172 Core

Mike Myers, Ben Lee

Jun 17, 1999

Al Gore appears on ""The Paul Shaffer Show""; The Hosie Cow Secret Word is ""tourniquet""; Mike Myers promotes Austin Powers 2.

S6·E173 Core

Julianna Margulies, Jon Stewart

Jun 18, 1999

Anton is introduced as Buddy Rich Jr., the ""bastard son"" of the legendary jazz drummer; Hosie Cow makes a cameo in the new Austin Powers movie; the Hosie Cow Secret Word is ""whi

S6·E174 Core

Felicity Huffman, Andy Dick, Elvis Costello

Jun 21, 1999

The secret word (""rodeo"") is now sponsored by Larry King, whom according to Alan ""looks like an owl""; ""Rita Buttgas"" (Jude Brennan) is introduced as the latest winner of the

S6·E175 Core

Adam Sandler, Missy Elliot

Jun 22, 1999

The Larry King Secret Word is ""gabardine,"" and is followed by stock footage of four baby owls devouring a rat. Also, Dave shows the audience an autographed photo of the US Women

S6·E176 Core

Geri Halliwell, Richard Belzer

Jun 23, 1999

Jimmy Vaughan sits in; the Larry King Secret Word is ""entropic""; after an unusually aimless edition of ""New for Summer,"" Dave asks Paul, ""What is happening to this show?""

S6·E177 Core

Rudolph Giuliani, Leslie Mann, The Pretenders

Jun 24, 1999

The Larry King Secret Word is ""linguine."" Also, to counteract with Hillary Clinton's recent decision to run for the US Senate in New York, Mayor Giuliani announces that he's run

S6·E179 Core

Colin Powell, Maurice Green

Jun 28, 1999

Tonight's Secret Word (""bird"") is brought to you by David Letterman's Women's World Cup Soccer Team, in honor of his latest celebrity crush. Quote Alan: ""They're hotter than a

S6·E180 Core

Mira Sorvino, Lyle Lovett

Jun 29, 1999

The World Cup Soccer Team Secret Word is ""oozing""; Montana park ranger (and past winner) ""Rita Buttgas"" (Jude Brennan) is announced as the winner of the Secret Word Tournament

S6·E182 Core

Calista Flockhart, Jack Hannah

Jul 1, 1999

The Larry King/Women's Soccer Secret Word is ""highoeyazmuhoodhee""; Calista Flockhart's chat with Dave is interrupted by visions of the dancing baby from Ally McBeal busting a mov

S6·E184 Core

John McEnroe, George Jones

Jul 5, 1999

Dave shows footage of a taxi literally crashing the staff cookout out on 53rd Street; with temperatures hovering over 100 degrees, Biff dares to go outside and fry an egg on the si

S6·E185 Core

Chris Rock, Sixpence None the Richer

Jul 6, 1999

An audience member attempts to button Dave's jacket; the Dan Quayle/Larry King/Women's Soccer Secret Word is ""neoprene""; throughout the night, Biff stands next to a 45-pound bloc

S6·E186 Core

Lindsay Davenport, Oliver Platt, Jeffrey Ross

Jul 7, 1999

Dave replies to a Zagat's survey; the Women's Soccer Secret Word is ""pestilence,"" with the Dan Quayle/Larry King Secret Word Jackpot standing at ""Thirteen hundred damn dollars!"

S6·E187 Core

Jay Thomas, Jason Briggs

Jul 8, 1999

The Secret Word is ""prick,"" with the stock footage of the baby owls eating the rat joining an already crowded group of sponsors; John Mayall sits in; Jason Biggs promotes America

S6·E188 Core

Naomi Campbell, Jimmie Walker, Lucinda Williams

Jul 9, 1999

Dave points out that Paul is dressed from head to toe in white tonight, including a snazzy top hat; during Mailbag, The Guy on Fire is profiled on ""Biff Henderson's Where Are They

S6·E189 Core

Don Rickles, Dave Mirra, Patty Griffin

Jul 19, 1999

The Larry King/Dan Quayle Secret Word is ""sphygmomanometer""; Dave briefly comments on the passing of JFK Jr.; Dave Mirra does bicycle stunts on 53rd Street, but after he has to c

S6·E191 Core

Matthew Broderick, Dennis Regan

Jul 21, 1999

The Hillary Clinton/Larry King Secret Word is ""mommy""; Dave asks a question to Einstein's Brain (voice of Alan Kalter); perfect game winner David Cone presents the Top Ten.

S6·E192 Core

Catherine Zeta-Jones, Buzz Aldrin, Jamiroquai

Jul 22, 1999

The Hillary Clinton/Larry King Secret Word is ""meehnkee""; Dave ""performs"" at Woodstock '99, then declares that Limp Bizkit kicks ass; Buzz Aldrin drops by to celebrate the 30th

S6·E193 Core

Charles Grodin, Alanis Morrisette

Jul 23, 1999

Paul asks what the point of the Secret Word is, and after it's revealed (""throb""), Dave replies with ""I'm tired of being held hostage by your psychotic delusions."" Also, Mujib

S6·E194 Core

Ted Koppel, Isabella Rossellini, Macy Gray

Jul 26, 1999

Paul complains about the heat at Woodstock '99; Dave brags about Max Pappas and Team Rahal (a sign of things to come); Ted Koppel's evil twin Kenny is caught hosting Nightline in l

S6·E197 Core

Bruce Willis, Heidi Klum

Jul 29, 1999

""Paul Shaffer's Countdown to the Millennium"" makes its triumphant return to the Late Show, and is now sponsered by Hillary Clinton and Larry King. Tonight's forecast: ""In the n

S6·E198 Core

Lance Armstrong, Barry White

Jul 30, 1999

Dave chats with Tour de France winner and cancer survivor Lance Armstrong; Paul's latest prediction: ""No more lox and bagels""; Sheryl Crow performs ""The Difficult Kind.""

S6·E199 Core

Pierce Brosnan, Saffron Burrows, Jim Jeter

Aug 2, 1999

It's a very special night as Jim Jeter is about to log his one millionth mile on his 1982 Toyota Starlet. After reaching the milestone, Dave buys him a new used car.

S6·E201 Core

Dave Foley, Jonathan Witherspoon, Old 97's

Aug 4, 1999

Dave shows the audience some stuff he bought on his recent vacation in a segment called ""Travel Souvenirs."" Later, ""Newsradio"" star Dave Foley promotes the movie ""Dick.""

S6·E203 Core

Ray Romano, Jeff Altman

Aug 6, 1999

During CBS Mailbag, Alan punches Dave. Later, Dave's former ""Starland Vocal Band Hour"" co-star Jeff Altman looks back at his tumultous television career.

S6·E204 Core

Regis Philbin, Dave Attell

Aug 9, 1999

Paul refers to Regis as a bastard, only for the ""Millionaire"" host to retaliate.

S6·E205 Core

Claire Danes, Smash Mouth

Aug 10, 1999

Kreskin's knowledge of 70's backup singers is tested in a segment called ""Commodore or Pip?"" Later, Smash Mouth performs their smash hit ""All-Star.""

S6·E206 Core

Hugh Grant, The Mavericks

Aug 11, 1999

Dave announces that a crack in the building next door caused a temporary evacuation of the theater. Later, The Mavericks perform ""There Goes My Heart.""

S6·E207 Core

Rene Russo, Tori Amos

Aug 12, 1999

Dave takes up an offering for a preacher who played ""Who Your Deer Repellants.""

S6·E208 Core

Shaquille O'Neal, Helen Mirren

Aug 13, 1999

During CBS Mailbag, Inky Mendez announces his candidacy for the US Senate, while Dave chats with ""Hillary Clinton"" (Gerard).

S6·E209 Core

Tony Danza, Katie Holmes, Robert Palmer

Aug 16, 1999

A shirtless Vince DeMentri interviews people on the street, asking them what they think of Hillary Clinton. Later, Katie Holmes promotes ""Dawson's Creek.""

S6·E210 Core

Lara Flynn Boyle, David Brenner, Everclear

Aug 17, 1999

Dave announces that tonight, ""We're going to have good old-fashioned fun"": all night, Richard Egan stands on 53rd St. guessing the weight of passersby.

S6·E212 Mytharc

Alec Baldwin, Dwight Yoakam

Aug 19, 1999

Dave announces that tonight is the premiere of ""Late Show Who Wants to be a Billionaire?"" Tonight's first question: ""Who took over for the 'Brady Bunch' father after the origin

S6·E213 Mytharc

Albert Brooks, Omar Epps

Aug 20, 1999

Dave announces that after 6 years and 1,278 shows on CBS, he now wants to be called ""Daddy""; Alan beats up Regis during CBS Mailbag; Albert Brooks makes a phone call to his pet p

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