| Monday, February 1, 1999 | |
|---|---|
| New York | Home of your world champion Denver Broncos |
| Dave | Super Bowl MVP |
| PostMonologue | Tony Randall covers the Super Bowl |
| Top Ten | Words That Kind of Sound like Elway (radio version) |
| 1st Guest | A flu-stricken Bill Cosby |
| 2nd Guest | Brendon Fraser |
| Music | Ricky Scruggs & Vince Gill |
| Sitting In | Nile Rodgers |
| Other | Coming up on the late show |
| Kiss me now | |
| Tuesday, February 2, 1999 | |
|---|---|
| New York | Shining star of the Caribbean |
| Dave | A man who has no shadow |
| PostMonologue | Who Asked for it? |
| Top Ten | Things Heard Outside "She's All That" |
| 1st Guest | Tom Arnold |
| Standup | David Brenner |
| 3rd Guest | Catherine Bell |
| Buy me some pants | |
| Wednesday, February 3, 1999 | |
|---|---|
| New York | Featuring 10% real fruit juice |
| Dave | King of the Flamenco guitar |
| PostMonologue | Historical Memorabilia |
| 2nd Bit | "John Elway" |
| Top Ten | Divas or Presidential Skin Conditions |
| 1st Guest | Tom Brokaw |
| 2nd Guest | Sean Patrick Flanery |
| Music | Creed |
| Return to your homes | |
| Thursday, February 4, 1999 | |
|---|---|
| New York | Site of the annual Chicago marathon |
| Dave | Real-life David Letterman |
| PostMonologue | Know Your Current Events |
| Top Ten | Hilary Clinton Campaign Slogans |
| 1st Guest | Mel Gibson |
| 2nd Guest | Laetitia Casta |
| Music | Fresh Step - Ya Gotta Be Fresh |
| Other | Coming up on the Late Show |
| No dice, Kenny | |
| Friday, February 5, 1999 | |
|---|---|
| New York | Real-life monkey town |
| Dave | The new coach of your Toronto Argonauts |
| PostMonologue | CBS Mailbag (Paul tries to explain the millenium to Dave) |
| Top Ten | Duties of the Miss USA Runner-up |
| 1st Slot | Stupid Pet Tricks |
| 2nd Guest | Martha Stewart |
| Standup | Mitch Hedberg |
| Sitting In all over | Nile Rodgers |
| Is the show over? | |
| Monday, February 8, 1999 | |
|---|---|
| New York | El Como Grande |
| Dave | Mayor of Dave Town |
| PostMonologue | Biff Henderson's America: Baker, NV |
| Top Ten | Historical Inaccuracies in "The 60's" |
| 1st Guest | Michael J. Fox |
| 2nd Guests | Rev. John and Ellena Cobb (kept apart by the post office) |
| Music | Willie Nelson |
| Go call the cops | |
| Tuesday, February 9, 1999 | |
|---|---|
| New York | The tri-state area's best kept secret |
| Dave | Future hall-of-famer |
| PostMonologue | The world of luggage (in Dallas) |
| Top Ten | Things Dumb Guys think Y2K Is |
| 1st Guest | Jeff Daniels |
| 2nd Guest | Fernanda Montenegro |
| Music | Monica |
| Time for the medicine | |
| Wednesday, February 10, 1999 | |
|---|---|
| New York | No reasonable offer refused |
| Dave | Your television friend |
| PostMonologue | Valentine's Day Cards |
| 2nd Bit | Bob Borden searches for a valentine |
| Top Ten | Jerry Falwell Pet Peeves about TV |
| 1st Guest | Robin Wright Penn |
| 2nd Guest | Richard Kind |
| Music | Chris Isaak - Flying |
| Do you like pants? | |
| Thursday, February 11, 1999 | |
|---|---|
| New York | Where everybody's been impeached |
| Dave | Making his network television debut |
| PostMonologue | Know Your Current Events (globetrotter) |
| Top Ten | Least Popular Self-Help Books |
| 1st Guest | Sandra Bullock |
| 2nd Guest | James Carville |
| Music | Hootie & The Blowfish |
| My head hurts | |
| Friday, February 12, 1999 | |
|---|---|
| New York | Standing room only |
| Dave | Crime-fighting veterinarian |
| PostMonologue | CBS Mailbag (Dave's shampoo commerical) |
| Top Ten | Valentine's Day Plans for This Guy |
| 1st Guest | Richard Simmons (under the impression that he's cupid) |
| 2nd Guest | Sarah O'Hare |
| Music | Ondar (throat singer) |
| Run like hell | |
| Monday, February 15, 1999 | |
|---|---|
| New York | The biggest little town in the world |
| Dave | The brilliant scientist who synthesized the element Lettermanium |
| PostMonologue | What they'll be doing after the impeachment trial |
| Top Ten | Thoughts Crossing Your Mind When Driving 200 mph (presented by Jeff Gordon) |
| 1st Guest | Bette Midler |
| 2nd Guest | David Hyde Pierce |
| Secret Word | Gristle |
| Do you smell taters? | |
| Tuesday, February 16, 1999 | |
|---|---|
| New York | Now hiring |
| Dave | The new Colonel Sanders |
| PostMonologue | Rejected FDA Products |
| Top Ten | Signs the President is Trying to Kill You |
| 1st Guest | Andy Garcia (fishy innuendo) |
| 2nd Guest | Tara Lipinksi |
| Standup | Wendy Liebman |
| Sitting In | Lou Soloff |
| Secret Word | Magnesium |
| Are you still up? | |
| Wednesday, February 17, 1999 | |
|---|---|
| New York | Just like the TV's Nanny, Fran Drescher |
| Dave | Founder of scientology |
| PostMonologue | Dog Show Quiz |
| Top Ten | Punchlines to Old Jokes that all West Point Cadets Must Know |
| 1st Guest | Andie MacDowell |
| 2nd Guest | Mike Judge |
| Music | Julian Lennon |
| Secret Word | Mongoose |
| Boy, I'm sleepy | |
| Thursday, February 18, 1999 | |
|---|---|
| New York | Maybe you've heard of us |
| Dave | Four-time rookie of the year |
| PostMonologue | Know Your Current Events (photographer) |
| Top Ten | Awards Won By David Letterman |
| 1st Guest | Magic Johnson |
| 2nd Guest | Jake Gyllenhaal |
| Music | Jewel - Down So Long |
| Secret Word | Hydraulic |
| Here kitty kitty | |
| Friday, February 19, 1999 | |
|---|---|
| New York | Reservations advised |
| Dave | As seen on TV |
| PostMonologue | CBS Mailbag (Stagehand Salute to Dave) |
| Top Ten | Things You Don't Want to Hear from a Hot Dog Vendor (as seen on the street) |
| 1st Guest | Greg Smith (kid "genius") |
| 2nd Guest | Lauren Bacall |
| Music | Sugar Ray |
| Secret Word | Buttress |
| Damn, I'm fat | |
| Monday, February 22, 1999 | |
|---|---|
| New York | Where a stranger is just someone you haven't filed charges against yet |
| Dave | Conductor of tonight's comedy train |
| PostMonologue | Dave's Video Collection |
| 2nd Bit | Alan Kalter's Saving the Thin Red Line |
| Top Ten | Mike Tyson Complaints About Television |
| 1st Guest | Matthew Broderick |
| Music | Sheryl Crow - You Don't Bring Me Anything But Down |
| I like pants | |
| Tuesday, February 23, 1999 | |
|---|---|
| New York | New, but not improved |
| Dave | A man who's laughing on the outside, but sleeping on the inside |
| PostMonologue | North or South Dakota? |
| Top Ten | Least Popular Grammy Categories |
| 1st Slot | Kid Scientists (chemoluminescence) |
| 2nd Guest | Governor Jesse Ventura |
| Secret Word | Bobcat |
| Is your name Connie? | |
| Wednesday, February 24, 1999 | |
|---|---|
| New York | Home to last year's Grammy awards |
| Dave | Hip Hop new-comer of the year |
| PostMonologue | Dave vs. Grammy Nominees |
| 2nd Bit | Star Wars feature story |
| Top Ten | Signs the Clintons are your Neighbors |
| 1st Guest | Uma Thurman |
| 2nd Guest | Tom Green |
| Performance | De La Guarda |
| Other | Live calls from Sweden |
| Secret Word | Barnacle |
| ---- | |
| Thursday, February 25, 1999 | |
|---|---|
| New York | The perfect hostess gift |
| Dave | The Grammy-winning brother-sister team |
| PostMonologue | Know Your Current Events |
| Top Ten | Ways Y2K Will Affect Disneyland |
| 1st Guest | Eriq La Salle |
| 2nd Guest | Homer Hickman |
| Music | Blondie - Maria |
| Secret Word | Crepuscular |
| Fix me a snack | |
| Friday, February 26, 1999 | |
|---|---|
| New York | A high-intensity part of your routine |
| Dave | British eccentric |
| PostMonologue | CBS Mailbag |
| Top Ten | Most Frequently Removed Tattoos |
| 1st Guest | James Coburn |
| 2nd Guest | Will Ferrall (with a little song) |
| Music | Marvelous Three |
| Secret Word | Combustible |
| Does your head hurt? | |