| 100% | BILLYRAYCYRUS | 13 | Country singer featured on an "Old Town Road" remix, helping it stay at #1 for 19 weeks: 3 wds. |
| 33% | BILLYRAYCYRUS | 13 | "Achy Breaky Heart" singer featured in the remix of "Old Town Road": 3 wds. |
| 28% | THEGREEKFREAK | 13 | Nickname for 19-Across, based on his athleticism and birth country: 3 wds. |
| 27% | TIMMCGRAW | 9 | "It's Your Love" singer whose songs have spent 73 weeks at #1 on Billboard's Hot Country chart: 2 wds. |
| 26% | JUSTINBIEBER | 12 | Pop star featured on a "Despacito" remix, propelling it to #1: 2 wds. |
| 25% | CHARLIXCX | 9 | Singer featured on Icona Pop's 2012 hit "I Love It": 2 wds. |
| 25% | TRISHAYEARWOOD | 14 | 19-Across, 44-Across, and "Forever Country" singer who turns 60 years old on September 19, 2024 (2 wds.) |
| 25% | STEVIEWONDER | 12 | "Superstition" singer featured on "That's What Friends Are For": 2 wds. |
| 25% | TOBYKEITH | 9 | "Red Solo Cup" singer whose songs have spent 53 weeks at #1 on Billboard's Hot Country chart: 2 wds. |
| 25% | KENNYCHESNEY | 12 | "The Good Stuff" singer whose songs have spent 72 weeks at #1 on Billboard's Hot Country chart: 2 wds. |
| 25% | LILNASX | 7 | Singer/rapper with the #1 Billboard hit "Old Town Road": 3 wds. |
| 25% | MISSYELLIOTT | 12 | Rapper featured on a "Last Friday Night (T.G.I.F.)" remix, propelling it to #1: 2 wds. |
| 24% | BILLYRAYCYRUS | 13 | Featured artist on Lil Nas X's "Old Town Road," the #7 song of the 2010s: 3 wds. |
| 24% | OLDTOWNROAD | 11 | 2019 Lil Nas X song that topped the charts for 19 weeks, the longest of the 2010s: 3 wds. |
| 24% | GLADYSKNIGHT | 12 | "Midnight Train to Georgia" singer featured on 1985's "That's What Friends Are For": 2 wds. |
| 24% | CHRISTIANKANE | 13 | Country singer who portrays an art/architecture expert on 15-Across: 2 wds. |
| 24% | KEITHURBAN | 10 | Country singer who was an "American Idol" judge for four seasons: 2 wds. |
| 23% | CHRISBROWN | 10 | "Forever" singer featured on three songs in Billboard's top 10 during a week in 2008: 2 wds. |
| 23% | LUKECOMBS | 9 | Singer whose 2023 hit "Fast Car" spent 8 weeks at #2 on the Billboard Hot 100 without hitting #1: 2 wds. |
| 23% | BREAKUPWITHHIM | 14 | Old Dominion No. 1 country single with the lyrics "Rip it off just like a Band-Aid / The way you look at me, girl, you can't pretend" (4 wds.) |
| 23% | RICKYSKAGGS | 11 | "Highways & Heartaches" country singer who turned 70 years old on July 18, 2024 (2 wds.) |
| 23% | EDSHEERAN | 9 | Singer whose 2015 hit "Thinking Out Loud" spent 8 weeks at #2 on the Billboard Hot 100 without hitting #1: 2 wds. |
| 23% | MORGANWALLEN | 12 | Country singer whose 2021 double album "Dangerous" spent its first 10 weeks atop the Billboard 200: 2 wds. |
| 23% | TIMMCGRAW | 9 | "Just to See You Smile" country singer who turned 50 on May 1, 2017 (2 wds.) |
| 23% | MISSYELLIOTT | 12 | Rapper whose 2002 hit "Work It" spent 10 weeks at #2 on the Billboard Hot 100 without hitting #1: 2 wds. |
| 23% | LILNASX | 7 | Rapper with the 2019 hit "Old Town Road": 3 wds. |
| 22% | LILNASX | 7 | Hip-hop and country rap singer with the 2019 country hit "Old Town Road": 3 wds. |
| 22% | CHARLIXCX | 9 | Pop singer featured on Iggy Azalea's 2014 #1 song "Fancy": 2 wds. |
| 22% | GIRLSLIKEYOU | 12 | Maroon 5 song featuring Cardi B that spent seven weeks at #1 on the Billboard Hot 100 in 2018 (3 wds.) |
| 22% | SUSANBANTHONY | 13 | Suffragette formerly featured on a $1 coin: 3 wds. |