| 100% | TOPTENLIST | 10 | Recurring "Late Night With David Letterman" segment involving a countdown: 3 wds. |
| 81% | SMALLTOWNNEWS | 13 | Recurring "Late Night With David Letterman" segment involving quirky journalism: 3 wds. |
| 72% | VIEWERMAIL | 10 | Recurring "Late Night With David Letterman" segment involving submissions from fans: 2 wds. |
| 43% | MERRILLMARKOE | 13 | "Late Night with David Letterman" head writer honored with the 2020 Laurel Award for TV Writing Achievement (2 wds.) |
| 34% | CONAN | 5 | Late-night host with a gag involving an orange blimp |
| 34% | CARPOOLKARAOKE | 14 | Recurring late-night sketch featuring 44-Across singing with famous people while driving (2 wds.) |
| 33% | LENO | 4 | Late-night host Jay with a recurring role in "Last Man Standing" |
| 32% | THELATESHOW | 11 | Previously hosted by David Letterman, and now starring Stephen Colbert, CBS talk-show that was a fierce competitor of 40-Across: 3 wds. |
| 32% | KIMMEL | 6 | Host Jimmy whose late-night show features a "Mean Tweets" recurring segment |
| 30% | TRIVIA | 6 | Night involving answering questions with a team |
| 30% | SHOW | 4 | "Late ___ With David Letterman" |
| 30% | CRAIGFERGUSON | 13 | Late-night host who's on CBS after David Letterman: 2 wds. |
| 29% | PET | 3 | Stupid ___ Tricks (recurring David Letterman "Late Show" segment) |
| 29% | JOANRIVERS | 10 | Late comedian/talk show host with a "watery" name: 2 wds. |
| 28% | REBELREBEL | 10 | 1974 David Bowie song with a repetitive title: 2 wds. |
| 28% | NUMBERTEN | 9 | Start of a David Letterman countdown |
| 28% | STATUEOFLIBERTY | 15 | Landmark with a torch: 3 wds. |
| 28% | LENO | 4 | Late-night host who competed with Letterman |
| 28% | CONAN | 5 | Late-night show with a redheaded host |
| 27% | CARPOOLKARAOKE | 14 | Segment on "The Late Late Show" where James Corden sings along with friends: 2 wds. |
| 27% | MARYKAY | 7 | Cosmetics company named for a woman with the last name Ash: 2 wds. |
| 26% | WALTONGOGGINS | 13 | "Fallout" actor with a featured role in "The White Lotus" season 3: 2 wds. |
| 26% | LATE | 4 | CBS's "___ Show With David Letterman" |
| 26% | INON | 4 | Involved with, as a plot (2 wds.) |
| 26% | ADAMSILVER | 10 | NBA commissioner whose last name is a metal with the chemical symbol Ag: 2 wds. |
| 26% | LESLIEBIBB | 10 | "Palm Royale" actress with a featured role in "The White Lotus" season 3: 2 wds. |
| 26% | SCHITTSCREEK | 12 | Sitcom set in Canada with a 2020 same-sex wedding between David and Patrick: 2 wds. |
| 26% | MEREDITHGREY | 12 | ABC TV character with a colorful last name, played by Ellen Pompeo since 2005: 2 wds. |
| 26% | TRACEYGOLD | 10 | "Growing Pains" actress whose last name is a metal with the chemical symbol Au: 2 wds. |
| 26% | SCOTTGLENN | 10 | "The Right Stuff" actor with a featured role in "The White Lotus" season 3: 2 wds. |