| 100% | LUDACRIS | 8 | Grammy winner with Usher and Lil Jon for "Yeah!" |
| 42% | ENYA | 4 | Grammy winner with songs in English, Irish and Elvish |
| 41% | STEVEMARSN | 10 | Grammy winner for comedy and banjo playing |
| 40% | ADELE | 5 | Grammy winner for the albums "21" and "25" |
| 40% | YEAH | 4 | Hit single from Usher featuring Lil Jon and Ludacris, that topped the US charts for 12 consecutive weeks |
| 37% | SELA | 4 | With 24-Across, Emmy winner for "Once and Again" |
| 37% | ALAN | 4 | With 24-Across, Emmy winner for acting, writing and directing |
| 36% | PATBENATAR | 10 | 1981 Grammy winner for "Fire and Ice" (Best Rock Vocal Performance, Female): 2 wds. |
| 36% | TED | 3 | With 74-Across, 2021 and 2022 Emmy winner for Outstanding Comedy Series |
| 36% | SEAN | 4 | With 57-Across, Best Actor Oscar winner for "Milk" and "Mystic River" |
| 35% | SEAN | 4 | With 38-Across, Best Actor Oscar winner for both "Mystic River" and "Milk" |
| 34% | ADELE | 5 | Grammy winner with the surname Adkins |
| 34% | RAP | 3 | Music genre for Lil' Kim and Lil Jon |
| 33% | SECADA | 6 | Singer Jon ___, Latin Grammy Award winner of 2017 with "To Beny More With Love" |
| 33% | YEAH | 4 | 2004 Usher hit featuring Lil Jon and Ludacris |
| 33% | NAS | 3 | Grammy winner Lil ___ X |
| 33% | ENYA | 4 | Grammy winner for "Amarantine" |
| 33% | ADELE | 5 | Grammy winner for "21" |
| 33% | ADELE | 5 | Grammy winner for "25" |
| 33% | LORDE | 5 | Grammy winner for "Royals" |
| 33% | ONLY | 4 | Song by Nicki Minaj featuring Drake and Lil Wayne, which was nominated for a Grammy at the 58th Grammy Awards |
| 33% | MYA | 3 | One-named singer who won a Grammy Award with Pink, Lil' Kim, and Christina Aguilera for "Lady Marmalade" |
| 32% | REHAB | 5 | Amy Winehouse 2008 Grammy Award for Song of the Year and Record of the Year winner |
| 32% | ETTAS | 5 | Grammy winner James and others |
| 32% | LLCOOLJ | 7 | Grammy winner for "Hey Lover" |
| 32% | JHUMPA | 6 | With 27-Across, Pulitzer Prize for Fiction winner who wrote 17-Across and 36-Across |
| 32% | AMYS | 4 | Grammy winners Winehouse and Grant |
| 32% | SCHMITT | 7 | Al ___, American recording engineer with 20 Grammy Awards for his work with Quincy Jones and Steely Dan |
| 32% | REHAB | 5 | 2008 Grammy Award for Song of the Year and Record of the Year winner by Amy Winehouse |
| 32% | KDLANG | 6 | Grammy winner for "Constant Craving," 1992 |