| 100% | GIRLSWANTGIRLS | 14 | 2021 Drake song whose title starts and ends with the same word: 3 wds. |
| 84% | NEVERSAYNEVER | 13 | 2021 Cole Swindell/Lainey Wilson song whose title starts and ends with the same word: 3 wds. |
| 83% | SORRYNOTSORRY | 13 | 2017 Demi Lovato song whose title starts and ends with the same word: 3 wds. |
| 48% | ANNAKENDRICK | 12 | "Pitch Perfect 3" star whose first and last names each start and end with the same letter: 2 wds. |
| 47% | URDU | 4 | Language whose name starts and ends with the same letter |
| 45% | OHIO | 4 | US state whose name starts and ends with the same letter |
| 44% | MAYBEIMAMAZED | 13 | 1970 Paul McCartney song whose title starts with an "answer": 3 wds. |
| 42% | LETITBE | 7 | 1970 Beatles song whose title follows the lyrics "Speaking words of wisdom": 3 wds. |
| 42% | OREGANO | 7 | Herb that starts and ends with the same letter |
| 42% | OHIO | 4 | State that starts and ends with the same letter |
| 42% | URDU | 4 | Language that starts and ends with the same letter |
| 41% | ANACONDA | 8 | Apex predator that starts and ends with the same letter |
| 41% | OREO | 4 | Food item that starts and ends with the same letter |
| 41% | OSLO | 4 | Northern European city that starts and ends with the same letter |
| 40% | PLEASEMRPLEASE | 14 | 1975 Olivia Newton-John hit whose title's first and last words are the same: 3 wds. |
| 40% | DAVIDTENNANT | 12 | 2005-2010 "Doctor Who" star whose first and last names each start and end with the same letter: 2 wds. |
| 40% | ELLIEGOULDING | 13 | "Love Me Like You Do" singer whose first and last names each start and end with the same letter: 2 wds. |
| 39% | ILIKEYOU | 8 | 2022 Post Malone and Doja Cat hit whose title ends with "(A Happier Song)": 3 wds. |
| 39% | SATISFYMYSOUL | 13 | Bob Marley and the Wailers song on "Kaya" whose title ends with a music genre (3 wds.) |
| 38% | NOSURPRISE | 10 | 2009 Daughtry song whose title starts with an "answer": 2 wds. |
| 37% | RHYMES | 6 | Words that end with the same sounds, like "moan" and "groan" |
| 36% | PULP | 4 | "___ Fiction," film whose title begins and ends with the letter "P" |
| 35% | SOMENIGHTS | 10 | #3 fun. hit with the same title as the album that 14-, 19- and 44-Across are on: 2 wds. |
| 35% | PORTLAND | 8 | Top 10 Drake song whose title is the same as an Oregon city, from his 2017 playlist "More Life" |
| 34% | OHIO | 4 | US state that begins and ends with the same letter |
| 34% | IBELIEVEICANFLY | 15 | R. Kelly hit whose last title word is aptly rhymed with "sky" in the lyrics ... and a hint to the starts of the other four longest puzzle answers |
| 33% | RHYME | 5 | End with the same sound, like "hike" and "bike" |
| 33% | RHYME | 5 | End with the same sound, like "jumps" and "mumps" |
| 33% | WINDOFCHANGE | 12 | 1991 Scorpions song with a weather word in the title (3 wds.) |