| 100% | THEWEEKND | 9 | Singer who collaborated with Ariana Grande on their 2014 top 10 song "Love Me Harder": 2 wds. |
| 43% | IGGYAZALEA | 10 | Rapper featured on Ariana Grande's 2014 top 10 song "Problem": 2 wds. |
| 42% | SHAWNMENDES | 11 | "Treat You Better" folk-pop singer who partnered with Justin Bieber on the 2020 top 10 song "Monster": 2 wds. |
| 39% | LANADELREY | 10 | "Doin' Time" singer who collaborates with 27-Across and 35-Across on the 2019 "Charlie's Angels" theme song "Don't Call Me Angel" (3 wds.) |
| 38% | DOLLYPARTON | 11 | "Jolene" singer who collaborated with Brad Paisley on the 2005 country hit "When I Get Where I'm Going": 2 wds. |
| 38% | EDSHEERAN | 9 | Singer who collaborated with Beyoncé on the 2017 #1 hit "Perfect Duet": 2 wds. |
| 37% | CAMILACABELLO | 13 | Singer who collaborated with Machine Gun Kelly in 2017 on the #4 hit "Bad Things": 2 wds. |
| 37% | SHERYLCROW | 10 | "All I Wanna Do" singer who collaborated with Kid Rock on his biggest pop hit, "Picture," in 2002: 2 wds. |
| 36% | NICKIMINAJ | 10 | Rapper featured on Ariana Grande's 2016 top 10 song "Side to Side": 2 wds. |
| 36% | MACMILLER | 9 | Rapper featured on Ariana Grande's 2013 top 10 song "The Way": 2 wds. |
| 34% | STEVIEWONDER | 12 | Singer who won the Oscar for Best Original Song, "Just Called to Say I Love You": 2 wds. |
| 34% | REGINABELLE | 11 | "Baby Come to Me" singer who collaborated with 44-Across on the R&B hits "Without You" and 34-Across (2 wds.) |
| 33% | DOLLYPARTON | 11 | Country Music Hall of Fame singer who collaborated with 15-Across and 43-Across on "Trio" (2 wds.) |
| 33% | LINDARONSTADT | 13 | Rock and Roll Hall of Fame singer who collaborated with 15-Across and 28-Across on "Trio" (2 wds.) |
| 33% | KATYPERRY | 9 | Singer who collaborated with Snoop Dogg on the 2010 No. 1 Billboard hit "California Gurls" (2 wds.) |
| 33% | SHEILAE | 7 | Singer/percussionist who collaborated with Prince on "Purple Rain" (2 wds.) |
| 32% | TIMEOFOURLIVES | 14 | 2014 top 10 Pitbull song released with Ne-Yo: 4 wds. |
| 32% | JIMMIEALLEN | 11 | "Best Shot" singer who collaborated with Brad Paisley on the 2021 country hit "Freedom Was a Highway": 2 wds. |
| 32% | EMMYLOUHARRIS | 13 | Country Music Hall of Fame singer who collaborated with 28-Across and 43-Across on the Grammy-winning 1987 album "Trio" (2 wds.) |
| 31% | LOUISARMSTRONG | 14 | Jazz singer and trumpeter who collaborated with 34-Across on three albums, including "Porgy and Bess": 2 wds. |
| 31% | TITIMEPREGUNTO | 14 | Top 10 song on 45-Across whose title translates to "Auntie Asked Me" (3 wds.) |
| 31% | ARIANAGRANDE | 12 | "7 Rings" pop singer who partnered with Justin Bieber on the 2020 #1 song "Stuck With U": 2 wds. |
| 31% | SEANPAUL | 8 | Rapper who collaborated with Beyoncé on the 2003 #1 hit "Baby Boy": 2 wds. |
| 30% | CHRISJANSON | 11 | Singer with the Top 10 country single "Buy Me a Boat" (2 wds.) |
| 30% | THANKUNEXT | 10 | Ariana Grande song with the lyric “One taught me love, one taught me patience” |
| 30% | PAULMCCARTNEY | 13 | Singer who performed "Maybe I'm Amazed" on the SNL40 anniversary special: 2 wds. |
| 30% | JUSTINBIEBER | 12 | Pop/R&B singer who's also topped the Country chart, thanks to "10,000 Hours" with Dan + Shay: 2 wds. |
| 30% | JOHNLEGEND | 10 | "All of Me" singer who's back, along with Gwen Stefani, as a veteran coach on "The Voice": 2 wds. |
| 30% | LIONELRICHIE | 12 | Singer who won the Oscar in 1986 for Best Original Song, "Say You, Say Me": 2 wds. |
| 30% | GWENSTEFANI | 11 | Singer who dueted with her beau Blake Shelton on "You Make It Feel Like Christmas": 2 wds. |