| 100% | THEWEEKND | 9 | "The Hills" R&B singer who got his seventh #1 hit with 38-Across: 2 wds. |
| 60% | ARIANAGRANDE | 12 | "Thank U, Next" pop singer who got her seventh #1 hit with a remix of 38-Across: 2 wds. |
| 46% | LUISFONSI | 9 | Singer who hit #1 in 2017 with the Spanish/English-language "Despacito": 2 wds. |
| 46% | EDSHEERAN | 9 | Singer who collaborated with Beyoncé on the 2017 #1 hit "Perfect Duet": 2 wds. |
| 46% | DOLLYPARTON | 11 | "Jolene" singer who collaborated with Brad Paisley on the 2005 country hit "When I Get Where I'm Going": 2 wds. |
| 45% | ARETHAFRANKLIN | 14 | Classic R&B singer with the 1967 hit "Chain of Fools": 2 wds. |
| 45% | KATYPERRY | 9 | Singer who collaborated with Snoop Dogg on the 2010 No. 1 Billboard hit "California Gurls" (2 wds.) |
| 45% | NATALIECOLE | 11 | R&B singer with the hits "Our Love" and "Miss You Like Crazy" (1950-2015): 2 wds. |
| 44% | TOBYKEITH | 9 | Singer who duetted with Willie Nelson on the 2003 #1 country hit "Beer for My Horses": 2 wds. |
| 44% | KANDIBURRUSS | 12 | R&B singer with Xscape who won season 3 of "The Masked Singer" as the Night Angel: 2 wds. |
| 44% | ARIANAGRANDE | 12 | "7 Rings" singer who reimagined 18-Across in a 2024 hit with the same title: 2 wds. |
| 42% | JOHNMELLENCAMP | 14 | "Jack & Diane" singer who had a hit in 1986 with "R.O.C.K. in the U.S.A.": 2 wds. |
| 42% | TODDRUNDGREN | 12 | Singer who came up with "Bang the Drum All Day" in his sleep: 2 wds. |
| 42% | JASONDERULO | 11 | "Wiggle" R&B singer who's had top 10 hits in each of the last three decades: 2 wds. |
| 42% | CAMILACABELLO | 13 | Singer who collaborated with Machine Gun Kelly in 2017 on the #4 hit "Bad Things": 2 wds. |
| 41% | REGINABELLE | 11 | "Baby Come to Me" singer who collaborated with 44-Across on the R&B hits "Without You" and 34-Across (2 wds.) |
| 41% | STEVIEWONDER | 12 | R&B singer who released the #1 album "Recorded Live: The 12 Year Old Genius" in 1963, at age 13: 2 wds. |
| 41% | CIARA | 5 | One-named R&B singer with the hit "1, 2 Step" |
| 41% | DIANAROSS | 9 | R&B singer who headlined the Essence Festival in New Orleans on June 30: 2 wds. |
| 41% | JUSTINBIEBER | 12 | Pop/R&B singer who's also topped the Country chart, thanks to "10,000 Hours" with Dan + Shay: 2 wds. |
| 40% | LUKECOMBS | 9 | Country singer who had a 2023 hit with his cover of Tracy Chapman's "Fast Car": 2 wds. |
| 40% | MACYGRAY | 8 | September-born R&B singer with the Top 10 hit "I Try" (2 wds.) |
| 40% | BRETTELDREDGE | 13 | "Somethin' I'm Good At" singer who topped the Billboard Country Albums chart with his latest LP: 2 wds. |
| 40% | LEEGREENWOOD | 12 | "I.O.U." singer who had a hit in 2001 with "God Bless the U.S.A.": 2 wds. |
| 40% | JIMMIEALLEN | 11 | "Best Shot" singer who collaborated with Brad Paisley on the 2021 country hit "Freedom Was a Highway": 2 wds. |
| 40% | KANEBROWN | 9 | R&B and country singer with the 2022 country hit "Thank God": 2 wds. |
| 40% | TIMBERLAKE | 10 | Justin ___, a singer famous for his hit single "Cry Me a River", who starred in the film "Friends with Benefits": 2 wds. |
| 40% | MARYTRAVERS | 11 | Folk singer who, in a trio with Peter and Paul, sang the 1963 hit "Puff, the Magic Dragon": 2 wds. |
| 39% | ALISONKRAUSS | 12 | "When You Say Nothing At All" singer who collaborated with Brad Paisley on the 2004 country hit "Whiskey Lullaby": 2 wds. |
| 39% | BILLYRAYCYRUS | 13 | Country singer who's also topped the Hot R&B/Hip-Hop chart, thanks to "Old Town Road" with Lil Nas X: 2 wds. |