| 100% | BEETSBYSKRILLEX | 15 | Sonny Moore's vegan venture that still retains rhythms from when he won all those Grammy Awards? |
| 81% | BEETSBYSKRILLEX | 15 | Sonny Moore's new vegan venture that still retains rhythms from when he won all those Grammy Awards? |
| 25% | ASLEEP | 6 | "When We All Fall ___, Where Do We Go?," studio album by Billie Eilish that won the Grammy Award for Album of the Year in 2020 |
| 24% | STILL | 5 | "___ Crazy After All These Years," 1975 hit album by Paul Simon which won him two Grammy Awards |
| 23% | MENATWORK | 9 | 15-Across and 33-Across rock band from Australia that won Best New Artist at the 1983 Grammy Awards (3 wds.) |
| 23% | ROLLING | 7 | With 18-Across, Adele single from the album "21" that won the Grammy Award for Record of the Year for 2011 |
| 22% | ROOM | 4 | "From A ___: Volume 1" country album by Chris Stapleton that won a Grammy Award in 2018 |
| 22% | SHAFT | 5 | "Who's the cat that won't cop out when there's danger all about?" |
| 22% | HELLO | 5 | Adele hit song that won three Grammy Awards |
| 22% | HELLO | 5 | 2015 Adele song that won three Grammy Awards |
| 21% | NAT | 3 | Bryce Harper when he won a 2015 M.V.P. award, e.g. |
| 21% | MORNINGPHASE | 12 | Beck album that won the 2015 Grammy Award for Best Rock Album: 2 wds. |
| 21% | THERESISTANCE | 13 | Muse album that won the 2011 Grammy Award for Best Rock Album: 2 wds. |
| 21% | INTERGALACTIC | 13 | Grammy Award-winning 1998 single from 44-Across's album "Hello Nasty" |
| 21% | BOBBY | 5 | ___ Darin, "Mack the Knife" musician who was 22 when he won the 1959 Grammy for Record of the Year |
| 21% | PAPER | 5 | "___ Towns," John Green's 2008 novel that won him the Edgar Award for best young adult novel |
| 21% | RAE | 3 | He's All That star Addison |
| 21% | DONTLETMEDOWN | 13 | The Chainsmokers song that won the 2017 Grammy Award for Best Dance Recording (4 wds.) |
| 21% | WASTINGLIGHT | 12 | Foo Fighters album that won the 2012 Grammy Award for Best Rock Album: 2 wds. |
| 21% | YOU | 3 | "I Will Remember ___," song by Canadian singer Sarah McLachlan that won her a Grammy Award |
| 21% | MAN | 3 | "When I Was Your ___," 2013 song by Bruno Mars from the studio album "Unorthodox Jukebox" that was nominated for Grammy Awards |
| 21% | SEAL | 4 | Singer who won three Grammy Awards for "Kiss from a Rose" |
| 21% | REHAB | 5 | 2006 Amy Winehouse hit that won three Grammy Awards in 2008 |
| 20% | DIARY | 5 | "The ___ of Alicia Keys" (R&B album that won three Grammy Awards) |
| 20% | LONELYBOY | 9 | 27-Across song that won two Grammy Awards in 2013 (2 wds.) |
| 20% | TIGHTENUP | 9 | 27-Across song that won a Grammy Award in 2011 (2 wds.) |
| 20% | PLATINUM | 8 | County album by Miranda Lambert that won a Grammy Award in 2015 |
| 20% | OBAMA | 5 | Former U.S. president who won a Best Spoken Word Album Grammy Award for the audiobook of "Dreams from My Father" |
| 20% | SHOTA | 5 | "He ___ portrait that won him an award.": 2 wds. |
| 20% | TRUTHHURTS | 10 | Viral 46-Across song that won the 2020 Grammy Award for Best Pop Solo Performance (2 wds.) |