| 100% | SAY | 3 | "___ Something," 2013 Grammy-winning duet by A Great Big World and Christina Aguilera |
| 68% | SAYSOMETHING | 12 | Song for which A Great Big World and Christina Aguilera won the Grammy for Best Pop Duo/Group Performance in 2015: 2 wds. |
| 38% | 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. |
| 36% | DUOS | 4 | Daft Punk and A Great Big World, for two |
| 32% | ART | 3 | "How Great Thou ___," 1967 album by Elvis Presley for which he won a Grammy Award |
| 31% | WHERE | 5 | "___ Are U Now," song by Skrillex, Diplo and Justin Bieber which won a Grammy in 2016 |
| 31% | UNFORGETTABLE | 13 | 1991 duet between 18- and 43-Across that won a Grammy |
| 31% | BEAUTY | 6 | "___ and a Beat," song by Justin Bieber featuring Nicki Minaj which won a Teen Choice Award in 2013 |
| 30% | UNAPOLOGETIC | 12 | Seventh studio album by Rihanna, that won her a Grammy in 2014 and had global hits like "Diamonds" and "Stay" |
| 30% | BERLINMARATHON | 14 | Event won by Eliud Kipchoge in a world-record time of two hours, one minute, and nine seconds (September, 2022) |
| 29% | AIMEEMANN | 9 | Grammy award winning female bassist who has been named one of the world's top ten greatest living songwriters by NPR: 2 wds. |
| 28% | BETTERMAN | 9 | 2016 song written by Taylor Swift and performed by 33-Across that won a Grammy Award for Best Country Duo/Group Performance (2 wds.) |
| 27% | MYA | 3 | One-named singer who won a Grammy Award with Pink, Lil' Kim, and Christina Aguilera for "Lady Marmalade" |
| 27% | RECORDOFTHEYEAR | 15 | Grammy award won by "Hello," "Get Lucky" and "Beat It" |
| 27% | ONTHEROADAGAIN | 14 | Song by 30-Across/33-Across that won a Grammy Award for Best Country Song and was inducted into the Grammy Hall of Fame (4 wds.) |
| 27% | KDLANG | 6 | Her “Crying” duet with Roy Orbison won a Grammy |
| 27% | SOPHIA | 6 | Loren who's won an Oscar and a Grammy |
| 27% | MUSICVIDEO | 10 | Grammy category won twice each by Taylor Swift, Beyoncé and Johnny Cash |
| 27% | THEBOOKTHIEF | 12 | 2013 film for which 46-Across won a Grammy Award (3 wds.) |
| 27% | CHEYENNEMOUNTAIN | 16 | … something big and rocky with a Space Force base in it |
| 26% | LINE | 4 | "Fall in ___," 2018 Christina Aguilera song featuring Demi Lovato which was nominated for a Grammy |
| 26% | TANEHISICOATES | 14 | "Between the World and Me" author who won a "genius grant" in 2015: 2 wds. |
| 26% | EYDIE | 5 | She and Steve won a 1960 Grammy for "We Got Us" |
| 26% | LAYLA | 5 | A hit song by Eric Clapton titled after a lady, that won a Grammy |
| 26% | ALLEY | 5 | "___ Cat," instrumental song by Bent Fabric which won a Grammy in 1963 |
| 26% | PLATINUM | 8 | County album by Miranda Lambert that won a Grammy Award in 2015 |
| 26% | INDUSTRYBABY | 12 | 2021 #1 song by Lil Nas X and 36-Across that was nominated for a Best Melodic Rap Performance Grammy Award and won three MTV Video Music Awards (2 wds.) |
| 26% | EBONYANDIVORY | 13 | Duet by Stevie Wonder and 47-Across that uses piano keys as a metaphor for racial harmony (3 wds.) |
| 26% | POMPOM | 6 | Something held and shaken by a cheerleader: Hyph. |
| 25% | BASIE | 5 | Jazz great who was the first African-American man to win a Grammy |