| 100% | VIEWERMAIL | 10 | Recurring "Late Night With David Letterman" segment involving submissions from fans: 2 wds. |
| 67% | SMALLTOWNNEWS | 13 | Recurring "Late Night With David Letterman" segment involving quirky journalism: 3 wds. |
| 67% | TOPTENLIST | 10 | Recurring "Late Night With David Letterman" segment involving a countdown: 3 wds. |
| 43% | MERRILLMARKOE | 13 | "Late Night with David Letterman" head writer honored with the 2020 Laurel Award for TV Writing Achievement (2 wds.) |
| 35% | CARPOOLKARAOKE | 14 | Recurring late-night sketch featuring 44-Across singing with famous people while driving (2 wds.) |
| 34% | CRAIGFERGUSON | 13 | Late-night host who's on CBS after David Letterman: 2 wds. |
| 28% | SHOW | 4 | "Late ___ With David Letterman" |
| 28% | AWINK | 5 | "He didn't sleep ___ last night" (at all): 2 wds. |
| 27% | TOPTEN | 6 | Type of list that David Letterman used to read: 2 wds. |
| 27% | PET | 3 | Stupid ___ Tricks (recurring David Letterman "Late Show" segment) |
| 26% | ARIANAGRANDE | 12 | "Thank U Next" singer who sings "Met Him Last Night" with Demi Lovato on "Dancing with the Devil ... the Art of Starting Over" (2 wds.) |
| 26% | LENO | 4 | Late-night host who competed with Letterman |
| 25% | JAMESCORDEN | 11 | English late night show host who was the co-creator of BBC's Gavin & Stacey: 2 wds. |
| 25% | EYETEST | 7 | Exam that involves reading from a distance: 2 wds. |
| 25% | STEPHENCOLBERT | 14 | American late night show host who wrote the book "I Am America (And So Can You!)": 2 wds. |
| 24% | CONAN | 5 | Late-night host with a gag involving an orange blimp |
| 24% | JIMMYKIMMEL | 11 | American late night show host who was the co-host of Comedy Central's "The Man Show": 2 wds. |
| 24% | LATE | 4 | CBS's "___ Show With David Letterman" |
| 24% | AHISTORYOF | 10 | With 47-Across, 1997 graphic novel by John Wagner, later made into a David Cronenberg film: 3 wds. |
| 24% | LENO | 4 | Late-night host Jay with a recurring role in "Last Man Standing" |
| 24% | LIGHTS | 6 | "___ Out with David Spade," late-night talk show hosted by David Spade |
| 23% | GUEST | 5 | "My Next ___ Needs No Introduction with David Letterman" |
| 23% | CHEE | 4 | Comedian and Late Night With Seth Meyers writer Karen |
| 23% | CHEE | 4 | "Late Night with Seth Meyers" staff writer Karen who regularly appears in "What Does Karen know?" segments |
| 23% | INON | 4 | Involved with, as a plot (2 wds.) |
| 23% | KIMMEL | 6 | Host Jimmy whose late-night show features a "Mean Tweets" recurring segment |
| 22% | JIMMYFALLON | 11 | Late-night host of NBC: 2 wds. |
| 22% | JIMMYKIMMEL | 11 | Late-night host of ABC: 2 wds. |
| 22% | JAMESCORDEN | 11 | "The Late Late Show with ___" host who voices another lead character in "Smallfoot'': 2 wds. |
| 22% | JAMESCORDEN | 11 | "The Late Late Show with ___" host, who voices Hi-5 in "The Emoji Movie": 2 wds. |