| 100% | PAPERPLANES | 11 | 2008 M.I.A. hit whose title includes things in the sky: 2 wds. |
| 78% | STRANGECLOUDS | 13 | 2011 B.o.B hit whose title includes things in the sky: 2 wds. |
| 68% | ALLTHESTARS | 11 | 2018 Kendrick Lamar/SZA hit whose title includes things in the sky: 3 wds. |
| 51% | DARLINGI | 8 | 2024 Tyler, the Creator hit whose title includes a term of endearment: 2 wds. |
| 46% | AGORAHILLS | 10 | 2023 Doja Cat hit whose title is a tribute to a town she lived in: 2 wds. |
| 45% | LIONELRICHIE | 12 | Singer in the Commodores whose solo hits include "All Night Long (All Night)": 2 wds. |
| 44% | ERICCLAPTON | 11 | English guitarist/singer in the Yardbirds and Cream whose solo hits include "Tears in Heaven": 2 wds. |
| 42% | JUDGEJUDY | 9 | 2024 Tyler, the Creator hit whose title is also a courtroom TV show: 2 wds. |
| 42% | DIANAROSS | 9 | Singer in the Supremes whose solo hits include "Upside Down": 2 wds. |
| 41% | SAYAAH | 6 | 2010 Trey Songz hit whose title sounds like a doctor's request: 2 wds. |
| 41% | ICECREAM | 8 | 2020 Blackpink and Selena Gomez hit whose title is a sweet treat: 2 wds. |
| 39% | PAULMCCARTNEY | 13 | English bassist/singer in the Beatles whose solo hits include "No More Lonely Nights": 2 wds. |
| 38% | CHASINYOU | 9 | 2020 Morgan Wallen hit whose music video features him driving around in a convertible: 2 wds. |
| 37% | LEEGREENWOOD | 12 | "I.O.U." singer who had a hit in 2001 with "God Bless the U.S.A.": 2 wds. |
| 37% | CLOUDNINE | 9 | Blissful place that's high in the sky: 2 wds. |
| 37% | 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 |
| 36% | LOVESONG | 8 | "Old Fashioned" thing in a Three Dog Night hit (2 wds.) |
| 36% | EYEOFTHETIGER | 13 | 1982 hit for Survivor with a sign of the Chinese zodiac in its title: 4 wds. |
| 36% | CRYPRETTY | 9 | Carrie Underwood album whose title track is a hit single (2 wds.) |
| 36% | JOHNMELLENCAMP | 14 | "Jack & Diane" singer who had a hit in 1986 with "R.O.C.K. in the U.S.A.": 2 wds. |
| 36% | DANCEMONKEY | 11 | 2019 hit for Tones and I with a sign of the Chinese zodiac in its title: 2 wds. |
| 36% | CRYPRETTY | 9 | 2018 Carrie Underwood album whose title track is a hit single (2 wds.) |
| 35% | STCHROMA | 8 | 2024 Tyler, the Creator hit whose title is his alter ego: 2 wds., abbr. |
| 35% | WILDESTDREAMS | 13 | 2015 Taylor Swift hit whose title suggests bedtime: 2 wds. |
| 35% | WHOSCRYINGNOW | 13 | 1981 Journey hit whose title is a question: 3 wds. |
| 35% | HOWYOULIKETHAT | 14 | 2020 Blackpink hit whose title is a question: 4 wds. |
| 35% | PORTLAND | 8 | 2017 Drake hit whose title is a city in Oregon |
| 35% | PARIS | 5 | 2017 Chainsmokers hit whose title is a city in France |
| 35% | THELOVEILOST | 12 | 1973 hit single by 44-Across and 30-Across with the lyrics "Take a good look at me / I'm in misery, can't you see?" (4 wds.) |
| 35% | SOUTHERNNIGHTS | 14 | 1977 Glen Campbell hit whose lyrics praise the "precious beauty" of the skies: 2 wds. |