| 100% | OOHLALA | 7 | "So beauuutiful!" (Also a Britney Spears song): 3 wds. |
| 56% | OOHLALA | 7 | Song performed by Britney Spears in "The Smurfs 2" who has a wax statue at Madame Tussauds, London: 3 wds. |
| 54% | OOHLALA | 7 | Song by Britney Spears in "Smurfs 2" which can also be used an exclamation: 3 wds. |
| 48% | TRL | 3 | The last music video it played was for a Britney Spears song |
| 48% | OOPS | 4 | Preceder of "I Did It Again" in a Britney Spears song title |
| 47% | OOPSIDIDITAGAIN | 15 | Britney Spears song with the lyric "That is just so typically me" |
| 42% | TOXIC | 5 | Britney Spears hit song with the lyric "A guy like you should wear a warning" |
| 40% | ILIKEIT | 7 | A 2010 hit song by Enrique Iglesias and Pitbull: 3 wds |
| 40% | IMA | 3 | Britney Spears song "___ Slave 4 U" |
| 39% | IMA | 3 | "___ Slave 4 U" (Britney Spears hit song) (2 wds.) |
| 39% | IMA | 3 | "___ Slave 4 U" (Britney Spears song): 2 wds. |
| 39% | IDID | 4 | "Oops! ... ___ It Again" (Britney Spears song): 2 wds. |
| 39% | OFME | 4 | "Piece ___" (2007 Britney Spears song) |
| 39% | OOH | 3 | "___ la la!" Britney Spears song |
| 39% | YOUWILLBEFOUND | 14 | Song from 16-Across that also serves as a Twitter hashtag within the show: 4 wds. |
| 39% | TEENER | 6 | Many a Britney Spears fan |
| 38% | OOH | 3 | "___ La La" (2013 Britney Spears song) |
| 38% | OOPS | 4 | "___!... I Did it Again," Britney Spears song |
| 37% | SUEME | 5 | Snide challenge which was also the name of a song on "Guys and Dolls": 2 wds. |
| 37% | BADGUY | 6 | 2019 song by Billie Eilish which also has a remix that features Justin Bieber: 2 wds. |
| 37% | PIECEOFME | 9 | Britney Spears song that begins, “I’m Miss American Dream” |
| 37% | OOH | 3 | "___ la la!" Britney Spears song from "Smurfs 2" |
| 37% | POPSTAR | 7 | Britney Spears, for example: 2 wds. |
| 36% | TICKETTORIDE | 12 | Board game named for a Beatles song: 3 wds. |
| 36% | THEHEARTWANTS | 13 | With 42-Across, Selena Gomez song whose title is also a Woody Allen quote: 3 wds. |
| 36% | LIKEABOSS | 9 | Parody of a Slim Thug song by The Lonely Island: 3 wds. |
| 35% | CIRCUS | 6 | 2008 song by Britney Spears with a music video that shows her as a ringmaster |
| 35% | SLAVE | 5 | "I'm a ___ 4 U" (2001 Britney Spears song) |
| 35% | DONTCRY | 7 | "___ Daddy," a song by Elvis Presley that he also performed as a duet with his daughter, Lisa Marie: 2 wds. |
| 35% | MAKEME | 6 | 2016 Britney Spears single featuring G-Eazy (2 wds.) |