| 100% | LUKECOMBS | 9 | Country singer whose cover of 27-Across's "Fast Car" was a #2 hit in 2023: 2 wds. |
| 61% | LUKECOMBS | 9 | Country singer who had a 2023 hit with his cover of Tracy Chapman's "Fast Car": 2 wds. |
| 51% | TRACYCHAPMAN | 12 | Singer whose song "Fast Car," from her self-titled debut album, was a #6 hit in 1988: 2 wds. |
| 48% | WHITNEYHOUSTON | 14 | Singer and actress who played Rachel Marron in 18a and whose cover of "I Will Always Love You" became a best-selling single: 2 wds. |
| 46% | ZACHBRYAN | 9 | "Heading South" country singer whose "Something in the Orange" hit the Billboard Top 10 in 2023: 2 wds. |
| 45% | LUKECOMBS | 9 | "Forever After All" country singer whose "The Kind of Love We Make" hit the Billboard Top 10 in 2022: 2 wds. |
| 43% | AGORAHILLS | 10 | 2023 Doja Cat hit whose title is a tribute to a town she lived in: 2 wds. |
| 42% | TANYATUCKER | 11 | "Delta Dawn" country singer who was honored with a star on the Hollywood Walk of Fame in 2020 (2 wds.) |
| 41% | SARAHMCLACHLAN | 14 | Canadian singer of "Adia" whose name's only vowels are A's: 2 wds. |
| 41% | JONIMITCHELL | 12 | 15-Across and 44-Across singer-songwriter who was honored with a Gershwin Award in 2023 (2 wds.) |
| 40% | BOBDYLAN | 8 | "Blowin' in the Wind" singer whose image appears on the cover of the Beatles' "Sgt. Pepper's Lonely Hearts Club Band" album: 2 wds. |
| 40% | CHUBBYCHECKER | 13 | Rock singer whose version of "The Twist" inspired a dance craze in the 1960s: 2 wds. |
| 40% | KENNYCHESNEY | 12 | Singer of the 2007 #1 country hit "Beer in Mexico": 2 wds. |
| 40% | BANGBANG | 8 | Jessie J/Ariana Grande/Nicki Minaj hit of 2014 whose title's only vowels are A's: 2 wds. |
| 40% | LORETTALYNN | 11 | "Coal Miner's Daughter" singer who was inducted into the Country Music Hall of Fame in 1988: 2 wds. |
| 40% | ALANJACKSON | 11 | Singer whose "Country Boy" hit #1 on the Billboard Hot Country Songs Chart in 2009: 2 wds. |
| 40% | SINEADOCONNOR | 13 | Singer whose "Nothing Compares 2 U" was a #1 song for four weeks in 1990 (2 wds.) |
| 40% | DOLLYPARTON | 11 | Country singer whose latest album, "I Believe In You," is geared toward children: 2 wds. |
| 39% | MORGANWALLEN | 12 | "7 Summers" country singer whose "You Proof" hit the Billboard Top 10 in 2022: 2 wds. |
| 39% | LUKECOMBS | 9 | Singer whose 2023 hit "Fast Car" spent 8 weeks at #2 on the Billboard Hot 100 without hitting #1: 2 wds. |
| 39% | LUKEBRYAN | 9 | Singer of the 2014 #1 country hit "Drink a Beer": 2 wds. |
| 39% | REDSEA | 6 | Mideast body of water whose parting was recapped in 15-Across in a bowl of tomato soup: 2 wds. |
| 39% | MARENMORRIS | 11 | 1-Across, 12-Across, 27-Across, and 50-Across country/pop singer who was named Female Vocalist of the Year by the Country Music Association in 2020 (2 wds.) |
| 39% | GLORIAESTEFAN | 13 | "Get On Your Feet" singer who was inducted into the Songwriters Hall of Fame in 2023: 2 wds. |
| 39% | ATTICUSFINCH | 12 | Justice-minded lawyer in "To Kill a Mockingbird" whose last name is a kind of bird: 2 wds. |
| 39% | TROYESIVAN | 10 | Singer of the 2015 hit "Youth" who was born in South Africa in 1995: 2 wds. |
| 39% | JEFFLYNNE | 9 | "Evil Woman" singer who was inducted into the Songwriters Hall of Fame in 2023: 2 wds. |
| 39% | SENECACRANE | 11 | Head Gamemaker in "The Hunger Games" whose last name is a kind of bird: 2 wds. |
| 39% | PIPERLAURIE | 11 | "Carrie" actress who played 27-Across's mother in "Children of a Lesser God": 2 wds. |
| 38% | FIONAAPPLE | 10 | "Criminal" singer whose last name is a shade of green: 2 wds. |