| 100% | REHAB | 5 | 2006 Amy Winehouse hit that won three Grammy Awards in 2008 |
| 53% | REHAB | 5 | Amy Winehouse hit that won three Grammys |
| 46% | HELLO | 5 | Adele hit song that won three Grammy Awards |
| 43% | HELLO | 5 | 2015 Adele song that won three Grammy Awards |
| 42% | REHAB | 5 | Amy Winehouse song that won three Grammys |
| 41% | PIECEOFME | 9 | Song by 32-Across that won three MTV Video Music Awards in 2008, including Video of the Year (3 wds.) |
| 41% | DIARY | 5 | "The ___ of Alicia Keys" (R&B album that won three Grammy Awards) |
| 40% | HELLO | 5 | Hit song by Adele that won 3 Grammy awards including Record of the Year in 2017 |
| 40% | AINTITFUN | 9 | Hit single by Paramore that won a Grammy Award for Best Rock Song in 2015 (3 wds.) |
| 39% | REHAB | 5 | Amy Winehouse track that won a Song of the Year Grammy |
| 37% | BTS | 3 | "Butter" K-Pop band that won three Kids' Choice Awards in 2021 |
| 36% | REHAB | 5 | 2006 Amy Winehouse hit |
| 36% | TRUTHHURTS | 10 | 1-Across hit that won Best Pop Solo Performance at the 2020 Grammy Awards: 2 wds. |
| 36% | BAHA | 4 | ___ Men (group that won a Grammy Award in 2001 for Best Dance Recording) |
| 36% | LONELYBOY | 9 | 27-Across song that won two Grammy Awards in 2013 (2 wds.) |
| 36% | TIGHTENUP | 9 | 27-Across song that won a Grammy Award in 2011 (2 wds.) |
| 35% | REHAB | 5 | Amy Winehouse 2008 Grammy Award for Song of the Year and Record of the Year winner |
| 35% | PLATINUM | 8 | County album by Miranda Lambert that won a Grammy Award in 2015 |
| 35% | NARUTO | 6 | Popular Japanese manga that won a Quill Award in 2006 |
| 34% | HELLO | 5 | Adele hit that won three Grammys |
| 34% | SINGLE | 6 | "___ Ladies (Put a Ring on It)," 2008 song by Beyonce that won three Grammy Awards |
| 34% | OFFICE | 6 | "The ___," American television show that won the Primetime Emmy Award for Outstanding Comedy Series in 2006 |
| 34% | AMYWINEHOUSE | 12 | "Back to Black" singer who won five Grammy Awards in 2008: 2 wds. |
| 34% | REHAB | 5 | Amy Winehouse hit that references Ray Charles and Donny Hathaway |
| 33% | ROLLING | 7 | "___ in the Deep," hit song by Adele that won 3 Grammy awards including Record of the Year in 2012 |
| 33% | DONTWANNAFIGHT | 14 | Alabama Shakes song that won the Grammy Award for Best Rock Song in 2016: 3 wds. |
| 33% | STAYHIGH | 8 | Brittany Howard song that won the Grammy Award for Best Rock Song in 2021: 2 wds. |
| 33% | ALJARREAU | 9 | Singer who won Grammy Awards in three different categories (jazz, pop, and R. & B.) |
| 33% | REHAB | 5 | 2008 Grammy Award for Song of the Year and Record of the Year winner by Amy Winehouse |
| 32% | SEAL | 4 | Singer who won three Grammy Awards for "Kiss from a Rose" |