| 100% | WHITNEYHOUSTON | 14 | "How Will I Know" singer with three diamond albums: 2 wds. |
| 67% | SHANIATWAIN | 11 | "You're Still the One" singer with three diamond albums: 2 wds. |
| 61% | WHITNEYHOUSTON | 14 | "How Will I Know" singer: 2 wds. |
| 47% | GARTHBROOKS | 11 | "Two Piña Coladas" singer with nine RIAA-certified diamond albums (at least 10 million sold): 2 wds. |
| 44% | JLO | 3 | Singer whose "This Is Me ... Now" album dropped in 2024, for short: 2 wds. |
| 44% | TAYLORDAYNE | 11 | Singer with the 1988 hit "Don't Rush Me": 2 wds. |
| 42% | BOBBYMCFERRIN | 13 | Singer with the 1988 hit "Don't Worry, Be Happy": 2 wds. |
| 42% | ALICIA | 6 | Singer Keys with the album "As I Am" |
| 41% | WILLOWSMITH | 11 | "Whip My Hair" singer with famous parents Will and Jada: 2 wds. |
| 41% | ALICIAKEYS | 10 | Singer with the #1 albums "As I Am" and "Girl on Fire" |
| 40% | KENNYROGERS | 11 | "Lady" singer with 14 platinum studio albums: 2 wds. |
| 40% | SHIRLEYMANSON | 13 | Scottish singer with the 2005 hit (with the band Garbage) "Bleed Like Me": 2 wds. |
| 40% | CHAPPELLROAN | 12 | Singer with the debut album "The Rise and Fall of a Midwest Princess": 2 wds. |
| 40% | DEMILOVATO | 10 | Singer with the 2020 love song "I Love Me" (2 wds.) |
| 40% | LISALOEB | 8 | Singer with the 1994 hit "Stay (I Missed You)": 2 wds. |
| 39% | WHITNEY | 7 | ___ Houston, "How Will I Know" African-American singer who is lovingly called "The Voice" |
| 39% | GARTHBROOKS | 11 | "Ask Me How I Know" singer who won the 2017 CMA Award for Entertainer of the Year (2 wds.) |
| 39% | ADELE | 5 | Singer with three age-named albums |
| 38% | SAMSMITH | 8 | "Stay With Me" singer/songwriter: 2 wds. |
| 38% | BILLIEEILISH | 12 | Singer-songwriter who sings "What Was I Made For?" on "Barbie: The Album" (2 wds.) |
| 38% | JUSTINBIEBER | 12 | "Yummy" singer with the 2021 #1 song at 16-Across and the #1 album at 44-Across: 2 wds. |
| 38% | JUSTINBIEBER | 12 | Singer with the 2020 love song "That's What Love Is" (2 wds.) |
| 38% | CHRISJANSON | 11 | Singer with the Top 10 country single "Buy Me a Boat" (2 wds.) |
| 38% | BRITNEYSPEARS | 13 | Singer with the 2001 hit "I'm a Slave 4 U": 2 wds. |
| 37% | REBA | 4 | Singer McEntire with the 2010 album "All the Women I Am" |
| 37% | ANAG | 4 | "I know I'm being ___, but ... " (reminder opening) (2 wds.) |
| 37% | PETERFRAMPTON | 13 | "I'm in You" singer with the hit single "Baby, I Love Your Way": 2 wds. |
| 37% | GARTHBROOKS | 11 | "Friends in Low Places" singer with 14 platinum studio albums: 2 wds. |
| 36% | PATSYCLINE | 10 | Country singer with the 1961 crossover hit "I Fall to Pieces": 2 wds. |
| 36% | JESSEMCCARTNEY | 14 | Pop singer with Dream Street who was the runner-up on season 3 of "The Masked Singer" as the Turtle: 2 wds. |