| 100% | NATE | 4 | Big __, book series like Diary of a Wimpy Kid |
| 64% | RODRICK | 7 | Second Diary of a Wimpy Kid book: __ Rules |
| 62% | DIARY | 5 | "___ of a Wimpy Kid" (Jeff Kinney book series) |
| 58% | DIARY | 5 | "___ of a Wimpy Kid" (book series) |
| 56% | KID | 3 | "Diary of a Wimpy ___" (Jeff Kinney book series) |
| 56% | KID | 3 | "Diary of a Wimpy __": Jeff Kinney book series |
| 54% | KID | 3 | "Diary of a Wimpy ___" (Jeff Kinney book series and a 2010 movie) |
| 54% | THEUGLYTRUTH | 12 | 2010 book that was #5 in the "Diary of a Wimpy Kid" series: 3 wds. |
| 54% | THETHIRDWHEEL | 13 | 2012 book that was #7 in the "Diary of a Wimpy Kid" series: 3 wds. |
| 54% | THELASTSTRAW | 12 | 2009 book that was #3 in the "Diary of a Wimpy Kid" series: 3 wds. |
| 53% | WIMPY | 5 | "Diary of a ___ Kid," book series by Jeff Kinney |
| 53% | KID | 3 | "Diary of a Wimpy ___" (book series) |
| 52% | DIARY | 5 | "___ of a Wimpy Kid" (Jeff Kinney kid-lit series) |
| 51% | KID | 3 | "Diary of a Wimpy ___," book series and media franchise created by Jeff Kinney that follows a middle-schooler |
| 50% | GREG | 4 | "Diary of a Wimpy Kid" kid |
| 50% | GREG | 4 | "Diary of a Wimpy Kid" protagonist |
| 50% | WIMPY | 5 | Meek, as in the title of a "Diary" series of kids' books |
| 50% | GREG | 4 | ___ Heffley, protagonist of the children's comedy book series "Diary of a Wimpy Kid" |
| 49% | JEFF | 4 | "Diary of a Wimpy Kid" writer/illustrator Kinney |
| 49% | GREG | 4 | Protagonist in "Diary of a Wimpy Kid" |
| 48% | GREGHEFFLEY | 11 | Main character of the "Diary of a Wimpy Kid" series by Jeff Kinney (2 wds.) |
| 46% | GREG | 4 | Kid in "Diary of a Wimpy Kid" |
| 46% | CHEESETOUCH | 11 | Schoolyard "affliction" similar to cooties in "Diary of a Wimpy Kid" (2 wds.) |
| 45% | WIMPY | 5 | "Diary of a ___ Kid" (children's book) |
| 43% | GREG | 4 | The kid in "Diary of a Wimpy Kid" |
| 43% | ZACHARYGORDON | 13 | Child actor who played 40-Across in the first three "Diary of a Wimpy Kid" films (2 wds.) |
| 43% | GREGHEFFLEY | 11 | Boy cartoonist portrayed by Zachary Gordon and Jason Drucker in the "Diary of a Wimpy Kid" movies: 2 wds. |
| 43% | DIARY | 5 | "___ of a Wimpy Kid: The Long Haul" (2017 movie) |
| 42% | ARNIE | 5 | Name of the titular anthropomorphic doughnut in a series of kid-lit books |
| 40% | NOBODY | 6 | The Diary of a __, humorous book by the Grossmiths |