| 100% | KID | 3 | "Diary of a Wimpy ___" (Jeff Kinney book series and a 2010 movie) |
| 74% | KID | 3 | "Diary of a Wimpy __": Jeff Kinney book series |
| 74% | KID | 3 | "Diary of a Wimpy ___," book series and media franchise created by Jeff Kinney that follows a middle-schooler |
| 70% | KID | 3 | "Diary of a Wimpy ___" (Jeff Kinney book series) |
| 60% | DIARY | 5 | "___ of a Wimpy Kid" (Jeff Kinney book series) |
| 58% | WIMPY | 5 | "Diary of a ___ Kid," book series by Jeff Kinney |
| 58% | THEUGLYTRUTH | 12 | 2010 book that was #5 in the "Diary of a Wimpy Kid" series: 3 wds. |
| 57% | GREGHEFFLEY | 11 | Main character of the "Diary of a Wimpy Kid" series by Jeff Kinney (2 wds.) |
| 52% | NATE | 4 | Big __, book series like Diary of a Wimpy Kid |
| 51% | DIARY | 5 | "___ of a Wimpy Kid" (Jeff Kinney kid-lit series) |
| 49% | KID | 3 | "Diary of a Wimpy ___" (book series) |
| 49% | RODRICK | 7 | Second Diary of a Wimpy Kid book: __ Rules |
| 48% | THETHIRDWHEEL | 13 | 2012 book that was #7 in the "Diary of a Wimpy Kid" series: 3 wds. |
| 48% | THELASTSTRAW | 12 | 2009 book that was #3 in the "Diary of a Wimpy Kid" series: 3 wds. |
| 48% | GREG | 4 | ___ Heffley, protagonist of the children's comedy book series "Diary of a Wimpy Kid" |
| 46% | GREGHEFFLEY | 11 | Boy cartoonist portrayed by Zachary Gordon and Jason Drucker in the "Diary of a Wimpy Kid" movies: 2 wds. |
| 45% | DIARY | 5 | "___ of a Wimpy Kid" (book series) |
| 44% | JEFF | 4 | "Diary of a Wimpy Kid" writer/illustrator Kinney |
| 44% | KID | 3 | "Diary of a Wimpy ___: Dog Days" (2012 movie) |
| 44% | THESANDMAN | 10 | 2022 Netflix adaptation of a Neil Gaiman comic book series starring 14-Across and 39-Across (2 wds.) |
| 43% | KID | 3 | "Diary of a Wimpy ___: The Long Haul" (upcoming movie) |
| 41% | FROSTNIXON | 10 | Play and movie about a noted 1977 series of interviews |
| 41% | BOND | 4 | ___ villain (evil mastermind from a series of novels and movies) |
| 40% | TRON | 4 | "___: Legacy," 2010 movie where Jeff Bridges plays the role of CLU via digital makeup and voiceover |
| 40% | HOLYGHOST | 9 | Book by John Sandford which was part of the "Virgil Flowers" novel series and became a NYT 2018 Bestseller: 2 wds. |
| 39% | DIARY | 5 | "___ of a Wimpy Kid: The Long Haul" (2017 movie) |
| 39% | TOPSY | 5 | Title twin sister in a series of children's books by Jean and Gareth Adamson |
| 38% | TITLE | 5 | Name of a movie or a book |
| 38% | ONE | 3 | "Ready Player ___," movie by Steven Spielberg which uses a lot of comic book and gaming references |
| 38% | WIMPY | 5 | Meek, as in the title of a "Diary" series of kids' books |