| New York | Proud home of the New York Yankees and the other team |
| Dave | The reason the mute button was invented |
| PostMonologue | Rerun - McDonald's Drive-Thru (November 1993) |
| 2nd Bit | Hairpiece, Not a Hairpiece |
| 1st Guest | Nicole Kidman |
| Music | Iggy Pop |
| Cute pants, sister |
| New York | No credit, bad credit, no problem |
| Dave | Sweetheart of the rodeo |
| PostMonologue | CBS Mailbag (Biff points) |
| Top Ten | NYC Tourist Questions |
| 1st Guest | Antonio Banderas |
| Standup | Jeffrey Ross |
| Other | Is this anything? |
| I smell gravy |
| New York | Discovered by 6th century missionaries |
| Dave | The feel good hit of the summer |
| PostMonologue | While We Were Gone |
| 2nd Bit | Stephanie's Brush with Death and Back to School Tips |
| 1st Guest | Will Ferrell |
| 2nd Guest | Tom Dreesen |
| Other | Is this anything? |
| I'm frightened |
| New York | Discovered by truffle hunting pigs |
| Dave | Last of the trans-Atlantic dirgibles |
| PostMonologue | Would You Like to Touch the Meat? |
| 2nd Bit | Is this Anything? (sponsored by Gail Norton, Department of the Interior) |
| 1st Guest | Bob Newhart |
| Music | Maxwell |
| Other | Condit ABC interview promo |
| I crave salty foods |
| New York | Moorish fortress until 932 |
| Dave | Reputed boss of the Letterman crime family |
| PostMonologue | Who Asked for It? |
| 1st Slot | National Hollerin' Champions |
| 2nd Guest | Julia Stiles |
| Music | Habib Koite & Bamada |
| I smell gravy |
| New York | Hey, check out the dude hanging off the Statue of Liberty |
| Dave | Recipient of the world's first self-contained artificial heart |
| PostMonologue | Rerun - Fun in a Car (Nov. 7, 1995) |
| 2nd Bit | John McEnroe Serves tennis balls across the street |
| 1st Guest | Brooke Shields |
| Music | Joe Henry |
| Other | Hairpiece, not a hairpiece |
| ---- |
| PostMonologue | CBS Mailbag |
| 2nd Bit | Gary Condit starts PR rehabilitation |
| Top Ten | Ways Condit can Improve his Image |
| 1st Guest | Eric Kraff (rubberband ball) |
| 2nd Guest | Goran Ivanisevic |
| Goodnight, Lois |
| New York | Set within an oasis of palm and olive trees |
| Dave | Director of the Department of City Planning |
| PostMonologue | Last Time |
| 1st Guest | Connie Chung |
| ---- |
| New York | Last vestige of the old frontier |
| Dave | Kentucky lottery official |
| PostMonologue | Psychic Sandwich |
| 2nd Bit | Is this anything? |
| 1st Guest | Jason Biggs |
| 2nd Guest | Daniel Tosh |
| Music | Etta James |
| Other | Tom Selleck |
| Who wants gum? |
| New York | Gateway to the dunes of the Sahara |
| Dave | A man who's been on a working vacation for 20 years |
| PostMonologue | US Open Quiz |
| 2nd Bit | Tony Mendez Show clip |
| Top Ten | Signs a Little League Player is Too Old |
| 1st Guest | Charles Grodin |
| Music | Michael Franti & Spearhead |
| The pants people |
| New York | We're closing in on Cats |
| Dave | CBS's employee of the decade |
| PostMonologue | Rerun - Taco Bell (June 17, 1996) |
| 1st Guest | Sarah Jessica Parker |
| 2nd Guest | John Witherspoon |
| More pants, Chester? |