| 100% | SHOW | 4 | "Late ___ With David Letterman" |
| 78% | LATE | 4 | CBS's "___ Show With David Letterman" |
| 77% | SMALLTOWNNEWS | 13 | Recurring "Late Night With David Letterman" segment involving quirky journalism: 3 wds. |
| 77% | TOPTENLIST | 10 | Recurring "Late Night With David Letterman" segment involving a countdown: 3 wds. |
| 76% | VIEWERMAIL | 10 | Recurring "Late Night With David Letterman" segment involving submissions from fans: 2 wds. |
| 56% | THETOPTEN | 9 | David Letterman shtick |
| 55% | CBS | 3 | David Letterman's network |
| 54% | TEN | 3 | David Letterman's Top ___ List |
| 53% | INARREARS | 9 | Late with one's payments |
| 51% | HOST | 4 | David Letterman or Jimmy Fallon, for example |
| 50% | NUMBERTEN | 9 | Start of a David Letterman countdown |
| 49% | DAVE | 4 | Letterman of late-night |
| 49% | NEWS | 4 | "ABC World ___ Tonight With David Muir" |
| 49% | CARR | 4 | Late media journalist David |
| 49% | CELLAR | 6 | Last place, with "the" |
| 49% | GAP | 3 | Feature of David Letterman's front teeth |
| 48% | ZOE | 3 | "Fashionably Late With Rachel ___" (Lifetime talk show) |
| 48% | SHOW | 4 | "The Late ___ With Stephen Colbert" |
| 48% | YEAR | 4 | With 28-Across, late December |
| 48% | TAFT | 4 | Last president with a mustache |
| 48% | TIDING | 6 | Satisfying until later, with "over" |
| 47% | TEN | 3 | Number of items in a David Letterman list |
| 47% | GAP | 3 | ___ teeth (dental feature for David Letterman and Madonna) |
| 47% | LIST | 4 | Top Ten ___ (what David Letterman would often read) |
| 47% | LENO | 4 | Letterman's late-night rival, formerly |
| 47% | HEWLETT | 7 | Cofounder of a tech company with David Packard |
| 47% | ENO | 3 | Brian who co-wrote "Heroes" with David Bowie |
| 47% | TOMHANKS | 8 | Letterman's last guest on NBC |
| 47% | GOLIATH | 7 | David killed him with a slingshot |
| 47% | SIDNEY | 6 | With 46-Across, late, legendary director |