| Friday, October 1, 1999 | |
|---|---|
| New York | Completely rebuilt after the 1906 earthquake and fire |
| Dave | The kitty cat's best friend |
| PostMonologue | CBS Mailbag |
| 2nd Bit | Why no punching? |
| Top Ten | University Classes Taught by Oprah Winfrey (upgraded #1) |
| 1st Guest | Kelsey Grammer |
| 2nd Guest | Rebecca Gayheart |
| I need help | |
| Monday, October 4, 1999 | |
|---|---|
| New York | It's malathia-licious! |
| Dave | Tony award-winning set designer |
| PostMonologue | Biff Henderson's America: Turkey, TX |
| 1st Guest | Harrison Ford |
| Music | David Bowie |
| We make pants for pets | |
| Tuesday, October 5, 1999 | |
|---|---|
| PostMonologue | Where can I get a decent meal in this town? (Hello Deli) |
| 2nd Bit | Late Show on Tour |
| 1st Guest | Dan Quayle |
| Music | Melissa Ethridge |
| Boy, I'm hungry | |
| Wednesday, October 6, 1999 | |
|---|---|
| New York | Beware dingos |
| Dave | A man who's 10% real juice |
| PostMonologue | Dave's Record Collection (with operatic interpretations) |
| 2nd Bit | True Stories of the Late Show Stagehands (Kenny & the Magic Lamp) |
| Top Ten | Things Don Zimmer Said After Being Hit in the Head |
| 1st Guest | Lili Tomlin |
| 2nd Guest | Leah Remini |
| Music | Beth Hart |
| Other | Bush Campaign commercial (a little too cocky) |
| Go call the cops | |
| Thursday, October 7, 1999 | |
|---|---|
| New York | Bottled in Maine |
| Dave | A man who's helping Hillary move |
| PostMonologue | Know Your Current Events/Soothing Lozenges... |
| 2nd Bit | Biff breaches presidential motorcade security |
| Top Ten | Tips for Living to be 100 Years Old (presented by 100-year-old professor) |
| 1st Guest | Jesse Ventura |
| 2nd Guest | Amy Brenneman |
| Music | ZZ Top |
| Time for the medicine | |
| Friday, October 8, 1999 | |
|---|---|
| New York | Do not chew or brush |
| Dave | A man who needs no introduction |
| PostMonologue | CBS Mailbag |
| Top Ten | Messages left by Siegried in the Middle of the Night by Roy |
| 1st Guest | Jack Hanna (wolverine) |
| Music | Sting - Brand New Day |
| 3rd Guest | Peter Fonda |
| Do you like pants? | |
| Monday, October 11, 1999 | |
|---|---|
| New York | The biggest little city in the world |
| Dave | A man who's not just a president, he's a client |
| PostMonologue | New York Shopping Items |
| Top Ten | Ways Columbus's Crew Passed Time on their 2-Month Voyage |
| 1st Guest | Bruce Willis (campaign commerical, stunt - live via satellite) |
| 2nd Guest | Will Ferrell |
| Sitting In | Carol King |
| My head hurts | |
| Tuesday, October 12, 1999 | |
|---|---|
| New York | Mommy, I'm on TV! |
| Dave | Accu-weather forecaster |
| PostMonologue | Where can I get a decent meal in this town? (Joe G's) |
| 2nd Bit | Trump/Winfrey campaign commercial (backlash) |
| Top Ten | Science Projects that won't be Winning a Nobel Prize |
| 1st Guest | Chazz Palminteri |
| 2nd Guest | Billy Blanks |
| Music | Wilson Pickett - Soul Survivor |
| Run like hell | |
| Wednesday, October 13, 1999 | |
|---|---|
| PreShow | Paul & Dave discuss tonight's guests |
| New York | Shark-free since '93 |
| Dave | Former wrestler and future politician |
| PostMonologue | Paul Fiori takes his driver's test |
| Top Ten | Donald Trump Campaign Slogans |
| 1st Guest | Farrah Fawcett |
| Worldwide Pants | |
| Thursday, October 14, 1999 | |
|---|---|
| New York | The beverage you're about to enjoy is extremely hot |
| Dave | The man whose novels epitomize the jazz age |
| PostMonologue | Know Your Current Events |
| Top Ten | Other Ways CBS is Pushing the Envelope |
| 1st Guest | John Malkovich |
| 2nd Guest | Harland Williams |
| Sitting In | Warren Zevon |
| Are you still up? | |
| Friday, October 15, 1999 | |
|---|---|
| New York | Do not take internally |
| Dave | Daredevil |
| PostMonologue | CBS Mailbag (Alan's Millenium Party Blowout Extravaganza) |
| 2nd Bit | Pat & Kenny Read Oprah Transcripts (Ricky Martin) |
| Top Ten | Things That Sound Creepy When Said by John Malkovich (presented by John Malkovich) |
| 1st Guest | Austin Payne (kid, heimliched his principal) |
| 2nd Guest | Patricia Arquette |
| Music | Moby - Natural Blues |
| Boy, I'm sleepy | |
| October 18 - 22, 1999 | |
|---|---|
| Monday | |
| Tuesday | |
| Wednesday | |
| Thursday | |
| Friday | |
| Reruns | |
| Monday, October 25, 1999 | |
|---|---|
| New York | Land of enchantment |
| Dave | Red shirt freshman |
| PostMonologue | Biff reports from the World Series in Atlanta |
| Top Ten | Signs Your Judge is on Drugs |
| 1st Guest | Charles Grodin |
| 2nd Guest | Jimmie Walker |
| Music | Buena Vista Social Club |
| Here kitty kitty | |
| Tuesday, October 26, 1999 | |
|---|---|
| New York | All the news that's fit to print |
| Dave | 280 lb. sophmore |
| PostMonologue | Where can I get a decent meal in this town? (Broadway Chili Company) |
| 2nd Bit | David Diaz gets revenge |
| Top Ten | Signs Martha Stewart is Nuts |
| 1st Guest | John Cusack |
| 2nd Guest | Bob Sarlatte |
| Music | LeAnn Rimes |
| Other | The band's presidential pictures, A Classic "Work with Me" Moment |
| Damn, I'm fat | |
| Wednesday, October 27, 1999 | |
|---|---|
| New York | Contents under pressure |
| Dave | A man with spring fever, or maybe just the flu |
| PostMonologue | Halloween Costumes |
| Top Ten | Other Jim Grey Regrets |
| 1st Guest | Martha Stewart |
| 2nd Guest | Martin Scorcese |
| Music | Ricky Martin |
| I like pants | |
| Thursday, October 28, 1999 | |
|---|---|
| New York | Home of your world champion New York Yankees |
| Dave | The mighty bambino |
| PostMonologue | Biff reports from the final game of the World Series |
| 2nd Bit | A moment from the Bradley-Gore Debate |
| Top Ten | Things the NY Yankees Have Always Wanted to Say |
| 1st Guest | Joe Torre |
| 2nd Guest | Denzel Washington (laying down the perfect bunt) |
| Is your name Connie? | |
| Friday, October 29, 1999 | |
|---|---|
| New York | Where every house is a haunted house |
| Dave | A man who can eat his weight in candy corn |
| PostMonologue | Know Your Current Events/Late Night Dining Options in Pepperel, MA... |
| 2nd Bit | Sharpshooter takes out Dave's billboard |
| Top Ten | Things You Don't Want to Hear at the Bottom of a World Series Pile-On |
| 1st Guest | Meryl Streep |
| Music | Natalie Merchant - Carnival |
| Other | World's largest pumpkin (don't miss it) |
| We love pumpkings [Mujibar] | |