| Grammy-winning Twain | 20 |
| Grammy-winning Tool song | 24 |
| Grammy-winning Tejano singer | 28 |
| Grammy-winning Steely Dan album of 1977 | 39 |
| Grammy-winning Steely Dan album | 31 |
| Grammy-winning soul singer India.___ | 36 |
| Grammy-winning soul singer India.__ | 35 |
| Grammy-winning soprano | 22 |
| Grammy-winning song of 1977 | 27 |
| Grammy-winning song by Toto | 27 |
| Grammy-winning song by Ray Charles | 34 |
| Grammy-winning single of 1958 | 29 |
| Grammy-winning singer: 1984 | 27 |
| Grammy-winning singer/guitarist Harper | 38 |
| Grammy-winning singer-songwriter Cohn | 37 |
| Grammy-winning singer Krall | 27 |
| Grammy-winning singer India.__ | 30 |
| Grammy-winning singer from Barbados | 35 |
| Grammy-winning singer Baker | 27 |
| Grammy-winning singer | 21 |
| Grammy-winning Sheryl Crow song | 31 |
| Grammy-winning Renaissance man Steve | 36 |
| Grammy-winning reggae singer Burning ___ | 40 |
| Grammy-winning reggae artist ___ Paul | 37 |
| Grammy-winning Redding | 22 |
| Grammy-winning rapper | 21 |
| Grammy-winning Radiohead album of 2000 | 38 |
| Grammy-winning Radiohead album | 30 |
| Grammy-winning R&Ber Joe | 28 |
| Grammy-winning R&B singer who covered "Imagine" in 2011 | 69 |
| Grammy-winning R&B singer India.___ | 39 |
| Grammy-winning R&B album of 1987 | 36 |
| Grammy-winning president | 24 |
| Grammy-winning pianist-singer | 29 |
| Grammy-winning pianist Floyd | 28 |
| Grammy-winning pianist Chick | 28 |
| Grammy-winning pianist born in the U.S.S.R. | 43 |
| Grammy-winning pianist | 22 |
| Grammy-winning Peter Gabriel video | 34 |
| Grammy-winning parody of 1984 | 29 |
| Grammy-winning New Ager | 23 |
| Grammy-winning New Age singer | 29 |
| Grammy-winning Nelly Furtado song . . . or a hint to the puzzle theme | 69 |
| Grammy-winning mezzo-soprano Anne __ von Otter | 46 |
| Grammy-winning merengue singer Tañón | 42 |
| Grammy-winning maestro ___ Solti | 32 |
| Grammy-winning King | 19 |
| Grammy-winning Jones | 20 |
| Grammy-winning jazz singer Diana | 32 |
| Grammy-winning Irish vocalist | 29 |
| Grammy-winning Irish singer | 27 |
| Grammy-winning Irish folk-rocker | 32 |
| Grammy-winning Herb | 19 |
| Grammy-winning Hayes | 20 |
| Grammy-winning gospel singer Winans | 35 |
| Grammy-winning Gorme | 20 |
| Grammy-winning Gnarls Barkley, e.g. | 35 |
| Grammy-winning Gloria | 21 |
| Grammy-winning Franklin | 23 |
| Grammy-winning Ford | 19 |
| Grammy-winning folk singer | 26 |
| Grammy-winning folk artist Steve | 32 |
| Grammy-winning Fitzgerald | 25 |
| Grammy-winning Erykah | 21 |
| Grammy-winning Eric Clapton tune | 32 |
| Grammy-winning Eric Clapton song | 32 |
| Grammy-winning Dr. | 18 |
| Grammy-winning diva | 19 |
| Grammy-winning country trio | 27 |
| Grammy-winning country star Steve | 33 |
| Grammy-winning country star of the 1980s, K.T. ___ | 50 |
| Grammy-winning country singer Ronnie | 36 |
| Grammy-winning country singer | 29 |
| Grammy-winning country group | 28 |
| Grammy-winning conductor | 24 |
| Grammy-winning concert pianist | 30 |
| Grammy-winning comedian from Atlanta | 36 |
| Grammy-winning Collins | 22 |
| Grammy-winning Christian metal band | 35 |
| Grammy-winning Chicago Symphony director | 40 |
| Grammy-winning Celtic musician | 30 |
| Grammy-winning cellist | 22 |
| Grammy-winning Carey | 20 |
| Grammy-winning British vocalist | 31 |
| Grammy-winning British guitarist Julian | 39 |
| Grammy-winning Brian | 20 |
| Grammy-winning Bonnie | 21 |
| Grammy-winning blues singer Thomas | 34 |
| Grammy-winning blues musician Robert | 36 |
| Grammy-winning blues guitarist Jonny | 36 |
| Grammy-winning Black Eyed Peas song | 35 |
| Grammy-winning Ben | 18 |
| Grammy-winning Baker | 20 |
| Grammy-winning Amy Winehouse song | 33 |
| Grammy-winning Aimee | 20 |
| Grammy-winning 2000 Radiohead album | 35 |
| Grammy-winning 1996 Beck album | 30 |
| Grammy-winning 1980 hit by The Police | 37 |
| Grammy-winning "We Are Young" band | 44 |
| Grammy-winning "Just Like You" Mo' | 48 |