| 100% | TOBYKEITH | 9 | Singer who duetted with Willie Nelson on the 2003 #1 country hit "Beer for My Horses": 2 wds. |
| 51% | TOBYKEITH | 9 | Singer (with Willie Nelson) of the 2003 song "Beer for My Horses": 2 wds. |
| 47% | MARIAHCAREY | 11 | Singer who duetted with Boyz II Men on 1995's "One Sweet Day," a #1 hit for 16 weeks: 2 wds. |
| 46% | EDSHEERAN | 9 | Singer who collaborated with Beyoncé on the 2017 #1 hit "Perfect Duet": 2 wds. |
| 42% | DADDYYANKEE | 11 | Rapper/singer who duetted with Luis Fonsi on 2017's "Despacito," a #1 hit for 16 weeks: 2 wds. |
| 42% | KATYPERRY | 9 | Singer who collaborated with Snoop Dogg on the 2010 No. 1 Billboard hit "California Gurls" (2 wds.) |
| 42% | ERIC | 4 | Singer Church who duetted with Keith Urban on the #1 country hit "Raise 'Em Up" |
| 42% | DOLLYPARTON | 11 | "Jolene" singer who collaborated with Brad Paisley on the 2005 country hit "When I Get Where I'm Going": 2 wds. |
| 42% | JIMMIEALLEN | 11 | "Best Shot" singer who collaborated with Brad Paisley on the 2021 country hit "Freedom Was a Highway": 2 wds. |
| 41% | KENDRICKLAMAR | 13 | Rapper who duetted with SZA on 2024's "Luther," a #1 hit for 13 weeks: 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. |
| 38% | SEANPAUL | 8 | Rapper who collaborated with Beyoncé on the 2003 #1 hit "Baby Boy": 2 wds. |
| 38% | CAMILACABELLO | 13 | Singer who collaborated with Machine Gun Kelly in 2017 on the #4 hit "Bad Things": 2 wds. |
| 36% | LUKEBRYAN | 9 | Singer of the 2014 #1 country hit "Drink a Beer": 2 wds. |
| 36% | GWENSTEFANI | 11 | Singer who dueted with her beau Blake Shelton on "You Make It Feel Like Christmas": 2 wds. |
| 34% | LUKECOMBS | 9 | Singer of the 2019 country hit "Beer Never Broke My Heart": 2 wds. |
| 34% | KENNYCHESNEY | 12 | Singer of the 2007 #1 country hit "Beer in Mexico": 2 wds. |
| 34% | JUSTINBIEBER | 12 | "Yummy" singer who was half the duet on 27-Across: 2 wds. |
| 34% | ARIANAGRANDE | 12 | "7 Rings" pop singer who partnered with Justin Bieber on the 2020 #1 song "Stuck With U": 2 wds. |
| 34% | CHARLEYPRIDE | 12 | "Kiss an Angel Good Mornin'" singer who was honored with the 1972 Grammy Award for Best Male Country Vocal Performance (2 wds.) |
| 33% | DOLLYPARTON | 11 | "Jolene" singer who received the CMAs' Willie Nelson Lifetime Achievement Award in 2016: 2 wds. |
| 33% | THEWEEKND | 9 | Stage name of "Starboy" singer who used the name for anonymity on YouTube: 2 wds. |
| 33% | ELTONJOHN | 9 | Pop star who sang a duet with Lady Gaga on his hit "Your Song" at the 2010 Grammys: 2 wds. |
| 33% | CHARLEYPRIDE | 12 | "Kiss an Angel Good Mornin'" singer who received the Willie Nelson Lifetime Achievement Award in 2020: 2 wds. |
| 33% | GLADYSKNIGHT | 12 | "Midnight Train to Georgia" singer who was the Bee on season 1 of "The Masked Singer": 2 wds. |
| 33% | ARIANAGRANDE | 12 | "7 Rings" singer who reimagined 18-Across in a 2024 hit with the same title: 2 wds. |
| 33% | SAMSMITH | 8 | Nonbinary singer who won an Oscar for the Bond theme "Writing's on the Wall": 2 wds. |
| 33% | KENNYROGERS | 11 | "The Gambler" singer who received the Willie Nelson Lifetime Achievement Award in 2013: 2 wds. |
| 33% | NORAHJONES | 10 | "Come Away With Me" singer who received the Grammys for both Album of the Year and Best New Artist in 2003: 2 wds. |
| 32% | LUKECOMBS | 9 | Country singer who had a 2023 hit with his cover of Tracy Chapman's "Fast Car": 2 wds. |