| 100% | ALANJACKSON | 11 | Singer whose "Country Boy" hit #1 on the Billboard Hot Country Songs Chart in 2009: 2 wds. |
| 76% | TRACEADKINS | 11 | Singer whose "Ladies Love Country Boys" hit #1 on the Billboard Country Songs Chart in 2007: 2 wds. |
| 64% | BROOKSANDDUNN | 13 | Duo whose "Play Something Country" hit #1 on the Billboard Country Songs Chart in 2005: 3 wds. |
| 62% | KENNYCHESNEY | 12 | "The Good Stuff" singer whose songs have spent 72 weeks at #1 on Billboard's Hot Country chart: 2 wds. |
| 61% | MARIAHCAREY | 11 | Singer whose song "We Belong Together" peaked at number one on the Billboard Hot 100 chart in 2005: 2 wds. |
| 60% | RICKYMARTIN | 11 | Singer whose song "Livin' La Vida Loca" peaked at number one on the Billboard Hot 100 chart in 1999: 2 wds. |
| 60% | BEYONCEKNOWLES | 14 | Singer whose song "Crazy In Love" featuring Jay Z peaked at number one on the Billboard Hot 100 chart in 2003: 2 wds. |
| 58% | TOBYKEITH | 9 | "Red Solo Cup" singer whose songs have spent 53 weeks at #1 on Billboard's Hot Country chart: 2 wds. |
| 58% | WHATSNEXT | 9 | Drake song that hit #1 on the Billboard Hot 100 in 2021: 2 wds. |
| 58% | TIMMCGRAW | 9 | "It's Your Love" singer whose songs have spent 73 weeks at #1 on Billboard's Hot Country chart: 2 wds. |
| 56% | FAITHHILL | 9 | Country singer whose song "Breathe" was named the #1 single on Billboard's year-end countdown in 2000 (2 wds.) |
| 55% | UPSIDEDOWN | 10 | 1980 50-Across song that hit #1 on the Billboard Hot 100, Disco, and Soul charts (2 wds.) |
| 55% | ARIANAGRANDE | 12 | "Yes, And?" singer who had two songs reach #1 on the Billboard Hot 100 in 2024: 2 wds. |
| 55% | OLIVIARODRIGO | 13 | Singer whose debut single "Drivers License" reached #1 on the Billboard Hot 100 in 2021: 2 wds. |
| 53% | MUDONTHETIRES | 13 | Studio album that was #1 on the "Billboard" Top Country Albums chart and whose title track was Brad Paisley's fourth #1 hit on the "Billboard" Hot Country Songs chart (4 wds.) |
| 53% | NICKIMINAJ | 10 | Rapper whose song "Anaconda" peaked at #2 on the Billboard Hot 100 in August 2014: 2 wds. |
| 53% | KEITHURBAN | 10 | Country star with 15 singles that hit #1 on the U.S. Hot Country Songs chart (2 wds.) |
| 52% | KELLYCLARKSON | 13 | Singer whose debut single "A Moment Like This" reached #1 on the Billboard Hot 100 in 2002: 2 wds. |
| 52% | MEGHANTRAINOR | 13 | Singer whose debut single "All About That Bass" reached #1 on the Billboard Hot 100 in 2014: 2 wds. |
| 52% | ZACHBRYAN | 9 | "Heading South" country singer whose "Something in the Orange" hit the Billboard Top 10 in 2023: 2 wds. |
| 52% | ANNAKENDRICK | 12 | Actress who had a song from "Pitch Perfect" chart on the Billboard Hot 100 in 2013: 2 wds. |
| 52% | ANNEHATHAWAY | 12 | Actress who had a song from "Les Misérables" chart on the Billboard Hot 100 in 2013: 2 wds. |
| 52% | LUKECOMBS | 9 | Singer whose 2023 hit "Fast Car" spent 8 weeks at #2 on the Billboard Hot 100 without hitting #1: 2 wds. |
| 52% | ISLANDSIN | 9 | With 40-Across, song that reached #1 on Billboard's country and Hot 100 charts in 1983: 2 wds. |
| 52% | THEWEEKND | 9 | "Starboy" pop singer who had 18 songs on the Billboard Hot 100 during a week in 2016: 2 wds. |
| 51% | LETTERTOME | 10 | Song from the album "5th Gear" that was Brad Paisley's sixth consecutive #1 hit on the "Billboard" Hot Country Songs chart (3 wds.) |
| 51% | EDSHEERAN | 9 | Singer whose 2015 hit "Thinking Out Loud" spent 8 weeks at #2 on the Billboard Hot 100 without hitting #1: 2 wds. |
| 51% | BRADLEYCOOPER | 13 | Actor who had a song from "A Star Is Born" chart on the Billboard Hot 100 in 2018: 2 wds. |
| 51% | MARIAHCAREY | 11 | "Honey" singer who's had three songs debut at #1 on the Billboard Hot 100: 2 wds. |
| 51% | LONDONBRIDGE | 12 | Fergie song that reached #1 on the Billboard Hot 100 in the summer of 2006: 2 wds. |