| 100% | HOWS | 4 | "___ the World Treating You" (Grammy-winning Alison Krauss/James Taylor duet) |
| 39% | RAISINGSAND | 11 | Bluegrass album by Robert Plant and Alison Krauss that won Album of the Year at the 2009 Grammy Awards (2 wds.) |
| 35% | WADE | 4 | James —, darts player who won the 2007 World Matchplay tournament |
| 32% | BAD | 3 | With 35-Across, Taylor Swift hit that won the 2016 Best Music Video Grammy |
| 31% | FOLKLORE | 8 | Album by Taylor Swift which won the Grammy for Album of the Year in 2021 |
| 31% | OZZY | 4 | ___ Osbourne, artist whose song "I Don't Want to Change the World" won the 1994 Grammy for Best Metal Performance |
| 30% | ADELE | 5 | "Someone Like You" singer who was 24 when she won the 2012 Grammy for Record of the Year |
| 30% | FRIEND | 6 | James Taylor song, You've Got a __ |
| 29% | TAKE | 4 | "Every Breath You ___," song performed by the Police that won the Grammy for Song of the Year in 1984 |
| 29% | SAY | 3 | "___ Something," 2013 Grammy-winning duet by A Great Big World and Christina Aguilera |
| 29% | BETTYWHITE | 10 | "The Proposal" actress who won a Grammy for the spoken word recording of her book "If You Ask Me": 2 wds. |
| 29% | EDSHEERAN | 9 | "Shape of You" singer who won two awards, including Best Pop Vocal Album, at the 2018 Grammy Awards (2 wds.) |
| 28% | ANN | 3 | Taylor of the fashion world |
| 28% | LOST | 4 | "Call Me If You Get ___," album by Tyler, the Creator that won the Grammy Award for Best Rap Album in 2022 |
| 28% | ASTAGE | 6 | "All the world," in "As You Like It" |
| 28% | ENTITLED | 8 | Acting like the world is owed to you |
| 28% | ALISON | 6 | Krauss, the leading female Grammy winner |
| 28% | LETSMAKELOVE | 12 | Duet by Faith Hill and Tim McGraw, released in 2000, that won the couple a Grammy for Best Country Collaboration with Vocals: 3 wds. |
| 28% | LIP | 3 | James Taylor "Oh Baby, Don't You Loose Your ___ on Me" |
| 27% | ILL | 3 | "___ stop the world and melt with you" (song lyric) |
| 27% | ASTRO | 5 | Winning player in the 2022 World Series |
| 27% | GUILLEN | 7 | Winning manager of the 2005 World Series |
| 27% | KNOCKEDEAD | 10 | "Show the world what you've got!" |
| 27% | SWEEP | 5 | Win the first four World Series games |
| 27% | MOCKINGBIRD | 11 | Carly Simon hit duet with James Taylor based on the lullaby "Hush Little Baby" |
| 27% | NOONECARES | 10 | "Let me play the world's smallest violin for you" |
| 27% | ETTA | 4 | James who won a 2003 Lifetime Achievement Grammy |
| 27% | SWEEP | 5 | Win the World Series in four games, say |
| 27% | SWEPT | 5 | Won the World Series in four games, say |
| 26% | REDS | 4 | Winning team in the "Black Sox Scandal" World Series |