| 100% | DONNYHATHAWAY | 13 | Singer of 15-Across who also sang duets with Roberta Flack: 2 wds. |
| 44% | MANDYMOORE | 10 | Singer of the hit 2000 single "I Wanna Be With You", who also voiced the role of Rapunzel in the animated film "Tangled": 2 wds. |
| 44% | BRUNOMARS | 9 | Singer of 15-Across and 29-Across who was born October 8, 1985 (2 wds.) |
| 41% | DOLLYPARTON | 11 | Country Music Hall of Fame singer who collaborated with 15-Across and 43-Across on "Trio" (2 wds.) |
| 40% | DIERKSBENTLEY | 13 | Singer of 15-Across and 29-Across who was awarded the 2018 Academy of Country Music's Merle Haggard Spirit Award (2 wds.) |
| 40% | LADYGAGA | 8 | Singer of 15-Across, 9-Down, and 22-Down who will appear in the 2018 remake of "A Star Is Born" (2 wds.) |
| 40% | DIERKSBENTLEY | 13 | Singer of "Home" and 15-Across: 2 wds. |
| 40% | PATSYCLINE | 10 | "Crazy" singer who also sang 1957's "Walkin' After Midnight": 2 wds. |
| 40% | LINDARONSTADT | 13 | Rock and Roll Hall of Fame singer who collaborated with 15-Across and 28-Across on "Trio" (2 wds.) |
| 40% | SAMSMITH | 8 | Grammy-winning singer of "Stay With Me," 15-Across, 20-Across, and 37-Across (2 wds.) |
| 39% | JENNIFERLOPEZ | 13 | 15-Across and 27-Across singer who was the first woman honored with a "Billboard" Icon Award (2 wds) |
| 38% | EDSHEERAN | 9 | "Shape of You" singer/songwriter who co-wrote and sings 36-Across with 28-Across (2 wds.) |
| 38% | BOBMARLEY | 9 | Singer whom 15-Across claims to be the reincarnation of: 2 wds. |
| 38% | GWENSTEFANI | 11 | Singer who dueted with her beau Blake Shelton on "You Make It Feel Like Christmas": 2 wds. |
| 37% | LUKECOMBS | 9 | 15-Across and 33-Across singer who won the 2019 Country Music Association's New Artist of the Year Award (2 wds.) |
| 37% | TOBYKEITH | 9 | Singer who duetted with Willie Nelson on the 2003 #1 country hit "Beer for My Horses": 2 wds. |
| 37% | LORETTADEVINE | 13 | Star of 15-Across who won an Emmy for a guest performance in "Grey's Anatomy": 2 wds. |
| 37% | NANCYSINATRA | 12 | "Somethin' Stupid" singer who also sang 1965's "These Boots Are Made for Walkin'": 2 wds. |
| 37% | JENNIFERLOPEZ | 13 | Singer/actress who also stars in 17-Across: 2 wds. |
| 37% | BRITNEYSPEARS | 13 | Singer of 15-Across and 50-Across known as the "Princess of Pop" (2 wds.) |
| 36% | RICOCASEK | 9 | Lead singer of The Cars who passed away September 15, 2019 (2 wds.) |
| 36% | FRANFINE | 8 | Title character of 15-Across, whose first name is shared by actress Drescher who plays her: 2 wds. |
| 36% | SAMSMITH | 8 | Grammy-winning singer of "Stay with Me," 15-Across, 20-Across, and 37-Across and the 2017 album "The Thrill of It All" (2 wds.) |
| 36% | DRAKE | 5 | Singer of 15-Across, 28-Across, and 38-Across who was honored with the Artist of the Decade Award at the 2021 "Billboard" Music Awards |
| 36% | RINGOSTARR | 10 | 19-Across drummer who also wrote and sang 31-Across: 2 wds. |
| 36% | MARIAHCAREY | 11 | Singer who duetted with Boyz II Men on 1995's "One Sweet Day," a #1 hit for 16 weeks: 2 wds. |
| 36% | SAMSMITH | 8 | Singer of the 2014 hit "Stay With Me": 2 wds. |
| 36% | SUMMERNIGHTS | 12 | Duet with the lyrics " I saved her life, she nearly drowned / He showed off, splashing around" sung by 15-Across and 40-Across in 43-Across (2 wds.) |
| 36% | SIDNEYPOITIER | 13 | Star of 15- and 34-Across who won an Oscar for "Lilies of the Field": 2 wds. |
| 35% | PEABO | 5 | Bryson who duetted with Roberta Flack on “Tonight, I Celebrate My Love” |