Season
- Season 1 1993-08-30
- Season 2 1994-08-29
- Season 3 1995-09-04
- Season 4 1996-09-02
- Season 5 1997-09-01
- Season 6 1998-08-31
- Season 7 1999-09-07
- Season 8 2000-08-21
- Season 9 2001-08-20
- Season 10 2002-09-03
- Season 11 2003-09-01
- Season 12 2004-08-23
- Season 13 2005-08-29
- Season 14 2006-08-28
- Season 15 2007-09-04
- Season 16 2008-09-02
- Season 17 2009-08-31
- Season 18 2011-01-03
- Season 19 2012-01-03
- Season 20 2013-01-02
- Season 21 2014-01-06
- Season 22 2014-09-02
Season 22 Episode
- Season 6 Jean-Claude Van Damme, Darryl Strawberry, Joe Cocker
- Season 6 Beau Bridges, Terrell Davis, Squirrel Nut Zippers
- Season 6 Terry Bradshaw, Jesse Jackson
- Season 6 Ray Romano, Chris Cardone, Tom Agna
- Season 6 Stupid Human Tricks, Jason Patric, Eve 6
- Season 6 Richard Simmons, Luisa Conlon
- Season 6 Andie MacDowell, Willie Nelson
- Season 6 Tim Forneris, Stephen Dorff, Wynonna
- Season 6 Charles Grodin, Paul Hopkins
- Season 6 Jack Hanna, Gretchen Mol, Nick Cave & The Bad Seeds
- Season 6 Cindy Crawford, Jeff Greenfield, Hootie & The Blowfish
- Season 6 Ben Stiller, Jackie Chan, Vince Gill
- Season 6 Bill Cosby, George Hamilton
- Season 6 Denis Leary, George Hamilton
- Season 6 Vince Vaughn, Brian Benben, Brian Setzer Orchestra
- Season 6 Michael J. Fox, Evander Holyfield, Dixie Chicks
- Season 6 Jennifer Lopez, Meredith Viera, Lyle Lovett
- Season 6 Stupid Pet Tricks, Marv Albert, Kevin James
- Season 6 Howard Stern, Katie Holmes
- Season 6 Jon Stewart, Jean Reno, Rob Zombie
- Season 6 Fran Drescher, Chris Kattan, Elvis Costello & Burt Bacharach
- Season 6 Chris Tucker, Faith Ford, Eagle Eye Cherry
- Season 6 Kelsey Grammer, Nick Mason, Tony Bennett
- Season 6 Drew Carey, Billy Connolly, Hedwig & The Angry Inch
- Season 6 Steve Martin, Cokie Roberts
- Season 6 Kelly Preston, Peter Boyle, Semisonic
- Season 6 Elizabeth & Bob Dole, Joaquin Phoenix
- Season 6 Jeff Goldblum, John Mellencamp
- Season 6 Isabella Rossellini, Stephen Baldwin, George Miller
- Season 6 Joan Lunden, Jeff Altman, Sheryl Crow
- Season 6 Mark McGwire, Robert Benigni, Bruce Hornsby
- Season 6 State Fair Champions, Ringo Starr
- Season 6 Jeff Daniels, David Cross, Mitch Hedberg
- Season 6 Danny Glover, Cal Ripken Jr., R.E.M.
- Season 6 Naomi Campbell, David Wells, R.E.M.
- Season 6 Danny DeVito, Joe Torre, Eddie Brill
- Season 6 Martin Short, Eddie Izzard, Phish
- Season 6 Daniel Baldwin, Todd Solondz, Phil Collins
- Season 6 Holly Hunter, Hunter S. Thompson, Garbage
- Season 6 Ted Danson, Denny Brauer, Black Sabbath
- Season 6 Anthony Hopkins, Buzz Aldrin, Depeche Mode
- Season 6 Queen Latifah, Ellie Lammer, Darrell Hammond
- Season 6 Adam Sandler, Jayson Williams, Soul Coughing
- Season 6 Denzel Washington, Father Mike Berner
- Season 6 George Pataki, Evan Metropoulis, P.J. Harvey
- Season 6 George Michael, Col. Gail Halverson, Hanson
- Season 6 Luke Perry, Tom Wolfe, Jay-Z
- Season 6 Melanie Griffith, Walter Cronkite, Travis Tritt
- Season 6 Roma Downey, Kenneth Branagh, Goo Goo Dolls
- Season 6 Donald Trump, Doug Flutie, Sarah Silverman
- Season 6 Kid Scientists, Cameron Diaz, Mariah Carey
- Season 6 Will Smith, Jack Hanna
- Season 6 Cher, Jerry Springer
- Season 6 Christian Slater, Celine Dion & Bryan Adams
- Season 6 Drew Barrymore, Siskel & Ebert
- Season 6 Helen Hunt, Ray Romano
- Season 6 Geena Davis, Martha Stewart, Roger Daltry
- Season 6 Gwyneth Paltrow, Peter Berg, Bonnie Raitt
- Season 6 Michael Caine, Art Donavon, Jewel
- Season 6 Salma Hayek, Marilyn Manson, Caroline Rhea
- Season 6 Patrick Stewart, Jon Stewart, Faith Hill
- Season 6 Greg Kinnear, Jane Horrocks, Reggie McFadden
- Season 6 Tom Hanks, Brooklyn Philharmonic
- Season 6 Meg Ryan, Whitney Houston
- Season 6 Tom Brokaw, Famke Janssen, Emmylou Harris
- Season 6 Robin Williams, Natalie Merchant
- Season 6 Val Kilmer, Ricky Williams, Billy Bragg & Natalie Merchant
- Season 6 Susan Sarandon, Marc Weinberg, Vienna Choir Boys
- Season 6 Jeff Goldblum, Angelina Jolie, Third Eye Blind
- Season 6 Julia Roberts, David Kelly
- Season 6 Barbara Walters, Josh Hartnett, Cyndi Lauper
- Season 6 Charles Grodin, John Witherspoon, Jessye Norman
- Season 6 John Travolta, Darlene Love
- Season 6 Chazz Palminteri, Ann Curry, Rufus Wainwright
- Season 6 James Woods, David Brenner, Cast of But Boy Could He Sing
- Season 6 Jay Thomas, Vinny Testaverde, Patti Smith
- Season 6 Stupid Human Tricks, Nathan Lane, St. Luke's Bottle Band
- Season 6 Jon Voight, Jena Malone, Louie C.K.
- Season 6 Sarah Jessica Parker, David Remnick, Bryan Callan
- Season 6 Jennifer Jason Leigh, Liam Aiken, Greg Behrendt
- Season 6 Mira Sorvino, Terry Bradshaw
- Season 6 Lisa Kudrow, Terry Bradshaw, Jason Kuller
- Season 6 Jon Stewart, Marv Albert, Jim Gaffigan
- Season 6 Gillian Anderson, Charlie Rose, Black Crowes
- Season 6 Robert Duvall, Al Franken, B.B. King
- Season 6 Conan O'Brian, Alanis Morrisette
- Season 6 William Baldwin, Trisha Yearwood, Scott Ferrall
- Season 6 Jack Hanna, Patricia Arquette
- Season 6 Yasmine Bleeth, Adam Carolla, James Brown
- Season 6 Alicia Silverstone, D.L. Hughley, Second Hand
- Season 6 Sophia Loren, The Mavericks
- Season 6 Bill Murray, Shania Twain
- Season 6 Cate Blanchett, Jason Schwartzman, Brandy
- Season 6 Bill Cosby, Brendon Fraser, Ricky Scruggs & Vince Gill
- Season 6 Tom Arnold, David Brenner, Catherine Bell
- Season 6 Tom Brokaw, Sean Patrick Flanery, Creed
- Season 6 Mel Gibson, Laetitia Casta, Fresh Step
- Season 6 Stupid Pet Tricks, Martha Stewart, Mitch Hedberg
- Season 6 Michael J. Fox, Rev. John & Ellena Cobb, Willie Nelson
- Season 6 Jeff Daniels, Fernanda Montenegro, Monica
- Season 6 Robin Wright Penn, Richard Kind, Chris Isaak
- Season 6 Sandra Bullock, James Carville, Hootie & The Blowfish
- Season 6 Richard Simmons, Sarah O'Hare, Ondar
- Season 6 Bette Midler, David Hyde Pierce
- Season 6 Andy Garcia, Tara Lipinksi, Wendy Liebman
- Season 6 Andie MacDowell, Mike Judge, Julian Lennon
- Season 6 Magic Johnson, Jake Gyllenhaal, Jewel
- Season 6 Lauren Bacall, Greg Smith, Sugar Ray
- Season 6 Matthew Broderick, Sheryl Crow
- Season 6 Kid Scientists, Jesse Ventura
- Season 6 Uma Thurman, Tom Green, De La Guarda
- Season 6 Eriq La Salle, Homer Hickman, Blondie
- Season 6 James Coburn, Will Ferrall, Marvelous Three
- Season 6 Brooke Shields, Peter Hillary
- Season 6 Ian McKellen, Reese Witherspoon, The Roots & Erykah Badu
- Season 6 Kid Turkey Callers, Mark Wahlberg, Fresh Step
- Season 6 Billy Crystal, George Miller
- Season 6 Chazz Palminteri, Jeff Altman, Everclear
- Season 6 Norm MacDonald, Jeff Beck
- Season 6 Elizabeth Hurley, Katie Holmes, Cake
- Season 6 Stupid Human Tricks, Craig Kilborn, Emmylou Harris, Linda Rondstadt, and Dolly Parton
- Season 6 Elton John, Henry Kissinger, LeAnn Rimes
- Season 6 Ron Howard, Charlotte Church
- Season 6 Marv Albert, Diane Lane, Blur
- Season 6 Laurence Fishburne, Sister Carol Anne Corley, Wilco
- Season 6 Steve Martin & Goldie Hawn, Jim Calhoun, Joe Henry
- Season 6 Dennis Hopper, Jason Nastke, The Corrs
- Season 6 Marilu Henner, Master P, Greg Fitzsimmons
- Season 6 Charles Grodin, David Arquette, Willie Nelson, Lyle Lovett, and Kris Kristofferson
- Season 6 Drew Barrymore, Scott Wolf, Barenaked Ladies
- Season 6 Lennox Lewis, Dr. Bertrand Piccard & Brian Jones
- Season 6 George Stephanopoulos, Molly Shannon, Andrea Bocelli
- Season 6 Bill Maher, Khalid El-Amin, Marc Maron
- Season 6 Elle Macpherson, Don Zimmer, John Mellencamp
- Season 6 Kevin Spacey, Tom Petty & The Heartbreakers
- Season 6 Kate Winslet, Darrell Hammond, Mandy Barnett
- Season 6 David Spade, Tim Couch, Eagle-Eye Cherry
- Season 6 John Cusack, Jack Hanna
- Season 6 Matthew Broderick, Ben Stein, The Cranberries
- Season 6 Martin Lawrence, Michelle Williams, Eddie Brill
- Season 6 Dustin Hoffman, Mary Steenburgen, Ben Folds Five
- Season 6 Ted Danson, Sarah Ferguson, Madness
- Season 6 Glenn Close, George Hamilton, Elvis Crespo
- Season 6 Tom Brokaw, Robbie Williams
- Season 6 Earvin Magic Johnson, Sara Gentile, Silverchair
- Season 6 Denny Brauer, Kelly Willis, Jesse Jackson
- Season 6 Brendan Fraser, Jesse Jackson, Bonnie Raitt
- Season 6 Kelsey Grammer, Steve Earle and the Del McCoury Band
- Season 6 Stupid Pet Tricks, Janeane Garofalo, Brian Regan
- Season 6 Ben Stiller, Camryn Manheim, Eve 6
- Season 6 Kathie Lee Gifford, Deana Carter
- Season 6 Kevin Kline, Leelee Sobieski, Beth Orton
- Season 6 Bill Cosby, Jon Favreau
- Season 6 Julia Roberts, Alice Cooper
- Season 6 Keri Russell, Aretha Franklin
- Season 6 Tom Selleck, Bob Barker, Leon Russell
- Season 6 Helen Hunt, Courtney Love, Hole
- Season 6 Natalie Portman, Tom Everett Scott, J. Geils Band
- Season 6 Harry Connick Jr., Damon Wayans
- Season 6 Kate Capshaw, Britney Spears
- Season 6 Kid Scientists, Sarah Jessica Parker, Mary Chapin Carpenter
- Season 6 Bill Murray, Everlast
- Season 6 Jennifer Lopez, Ira Glass
- Season 6 Dan Rather, Nancy Mace, Randy Newman
- Season 6 Jeff Foxworthy, Kristin Davis, Snoop Dogg
- Season 6 Timothy Hutton, Christine Lahti, Cast of It Ain't Nothing But the Blues
- Season 6 Ray Romano, Jewel
- Season 6 Heather Graham, David Wells
- Season 6 Tim Robbins, Oscar De La Hoya, Dane Cook
- Season 6 Roseanne, Susan Tedeschi
- Season 6 David Schwimmer, Brandi Chastain, Seth Green
- Season 6 Mike Myers, Ben Lee
- Season 6 Julianna Margulies, Jon Stewart
- Season 6 Felicity Huffman, Andy Dick, Elvis Costello
- Season 6 Adam Sandler, Missy Elliot
- Season 6 Geri Halliwell, Richard Belzer
- Season 6 Rudolph Giuliani, Leslie Mann, The Pretenders
- Season 6 Joey Lauren Adams, Spike Lee, Santana
- Season 6 Colin Powell, Maurice Green
- Season 6 Mira Sorvino, Lyle Lovett
- Season 6 Piedmont Bird Callers, Avery Johnson, June Carter Cash
- Season 6 Calista Flockhart, Jack Hannah
- Season 6 Stupid Human Tricks, John Leguizamo, Ziggy Marley & The Melody Makers
- Season 6 John McEnroe, George Jones
- Season 6 Chris Rock, Sixpence None the Richer
- Season 6 Lindsay Davenport, Oliver Platt, Jeffrey Ross
- Season 6 Jay Thomas, Jason Briggs
- Season 6 Naomi Campbell, Jimmie Walker, Lucinda Williams
- Season 6 Don Rickles, Dave Mirra, Patty Griffin
- Season 6 U.S. 1999 World Cup Women's Soccer Team, Jim Gaffigan
- Season 6 Matthew Broderick, Dennis Regan
- Season 6 Catherine Zeta-Jones, Buzz Aldrin, Jamiroquai
- Season 6 Charles Grodin, Alanis Morrisette
- Season 6 Ted Koppel, Isabella Rossellini, Macy Gray
- Season 6 National Hollerin' Champions, Garry Marshall, Los Lobos
- Season 6 Samuel L. Jackson, Rita Wilson, Pete Townshend & Eddie Vedder
- Season 6 Bruce Willis, Heidi Klum
- Season 6 Lance Armstrong, Barry White
- Season 6 Pierce Brosnan, Saffron Burrows, Jim Jeter
- Season 6 Tom Arnold, Q-Tip & Busta Rhymes
- Season 6 Dave Foley, Jonathan Witherspoon, Old 97's
- Season 6 William H. Macy, George Miller, The Pretenders
- Season 6 Ray Romano, Jeff Altman
- Season 6 Regis Philbin, Dave Attell
- Season 6 Claire Danes, Smash Mouth
- Season 6 Hugh Grant, The Mavericks
- Season 6 Rene Russo, Tori Amos
- Season 6 Shaquille O'Neal, Helen Mirren
- Season 6 Tony Danza, Katie Holmes, Robert Palmer
- Season 6 Lara Flynn Boyle, David Brenner, Everclear
- Season 6 Andie MacDowell, French Stewart, Tom Dreesen
- Season 6 Alec Baldwin, Dwight Yoakam
- Season 6 Albert Brooks, Omar Epps
Late Show with David Letterman - Season 6 Episode 158 Natalie Portman, Tom Everett Scott, J. Geils Band
6.33 63 minutes 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, showing Carlton Fisk's 1975 World Series homer three times; Bill DeLace impersonates a hot dog vendor a remote Top Ten; Nomar Garciaparra walks across the stage to a Standing O; Natalie Portman promotes Star Wars Episode I: The Phantom Menace.
