| 100% | WILLIENELSON | 12 | Country superstar who sings "Pretty Paper" with Dolly Parton on "A Holly Dolly Christmas" (2 wds.) |
| 62% | MICHAELBUBLE | 12 | Canadian crooner who sings "Cuddle Up, Cozy Down Christmas" with Dolly Parton on "A Holly Dolly Christmas" (2 wds.) |
| 61% | JIMMYFALLON | 11 | Late-night host who sings "All I Want for Christmas Is You" with Dolly Parton on "A Holly Dolly Christmas" (2 wds.) |
| 44% | TONYBENNETT | 11 | Crooner who sang a duet with Lady Gaga on the standard "Cheek to Cheek" at the 2015 Grammys: 2 wds. |
| 44% | ELTONJOHN | 9 | Pop star who sang a duet with Lady Gaga on his hit "Your Song" at the 2010 Grammys: 2 wds. |
| 43% | WILLIE | 6 | With 32-Across, country legend who sang "On the Road Again": 2 wds. |
| 41% | JIMMIEALLEN | 11 | "Best Shot" singer who collaborated with Brad Paisley on the 2021 country hit "Freedom Was a Highway": 2 wds. |
| 40% | BILLYPRESTON | 12 | Singer who sang with Nat King Cole on a TV show at 11 and released his first album at 16: 2 wds. |
| 40% | DIERKSBENTLEY | 13 | Country star with the 2016 hit single "Somewhere on a Beach": 2 wds. |
| 38% | DEBBIEGIBSON | 12 | "Electric Youth" singer who sings "Heartbreak Holiday" with 18-Across and "White Christmas" with her father on 30-Across (2 wds.) |
| 38% | MATTLEBLANC | 11 | "Friends" actor who plays Adam Burns on "Man With a Plan": 2 wds. |
| 38% | TANYATUCKER | 11 | "Delta Dawn" country singer who was honored with a star on the Hollywood Walk of Fame in 2020 (2 wds.) |
| 37% | BLAKESHELTON | 12 | "Nobody but You" country singer who's been a coach on "The Voice" since 2011: 2 wds. |
| 37% | KEVINNEALON | 11 | "Weeds" actor who plays Adam's brother Don on "Man With a Plan": 2 wds. |
| 37% | REBAMCENTIRE | 12 | Grammy-winning country star who plays a singer on 32-Across: 2 wds. |
| 37% | REBAMCENTIRE | 12 | Red-haired country singer who's in her first season as a coach on "The Voice": 2 wds. |
| 37% | GWENSTEFANI | 11 | Singer who dueted with her beau Blake Shelton on "You Make It Feel Like Christmas": 2 wds. |
| 37% | BILLYBOB | 8 | With 48-Across, "Bad Santa" star who played a serial killer on FX's "Fargo": 2 wds. |
| 36% | DEREKHOUGH | 10 | "Dancing With the Stars" dancer who's a judge on "World of Dance": 2 wds. |
| 36% | JOHNLEGEND | 10 | "All of Me" singer who's back, along with Gwen Stefani, as a veteran coach on "The Voice": 2 wds. |
| 36% | BYEBYE | 6 | With 32-Across, 1963 musical film in which 46-Across sings "Put on a Happy Face": 2 wds. |
| 36% | LUKECOMBS | 9 | Country singer who had a 2023 hit with his cover of Tracy Chapman's "Fast Car": 2 wds. |
| 36% | FREDDYKRUEGER | 13 | "A Nightmare on Elm Street" villain who wears a glove fitted with razor-sharp blades: 2 wds. |
| 36% | THOMASRHETT | 11 | Singer/songwriter who collaborated with 17-Across, 28-Across, Reba McEntire, and Keith Urban on the country hit "Be a Light" (2 wds.) |
| 36% | DANICAPATRICK | 13 | Race car driver who ate a scorpion on "Running Wild With Bear Grylls" in 2021: 2 wds. |
| 36% | KENDRICKLAMAR | 13 | Rapper who duetted with SZA on 2024's "Luther," a #1 hit for 13 weeks: 2 wds. |
| 36% | CINDYCRAWFORD | 13 | American supermodel with a beauty mark who appeared on more than 1,000 magazine covers: 2 wds. |
| 36% | MARYTRAVERS | 11 | Folk singer who, in a trio with Peter and Paul, sang the 1963 hit "Puff, the Magic Dragon": 2 wds. |
| 35% | BOBSAGET | 8 | "Fuller House" actor who was a roastee on Comedy Central Roast with John Stamos as the roast master: 2 wds. |
| 35% | TOBYKEITH | 9 | Singer who duetted with Willie Nelson on the 2003 #1 country hit "Beer for My Horses": 2 wds. |