| 100% | ITRY | 4 | 2000 Macy Gray hit song: 2 wds. |
| 83% | ITRY | 4 | Macy Gray hit song: 2 wds. |
| 72% | ITRY | 4 | 1999 hit song by Macy Gray: 2 wds. |
| 68% | ITRY | 4 | Macy Gray hit: 2 wds. |
| 60% | ITRY | 4 | Macy Gray's biggest hit: 2 wds. |
| 58% | ITRY | 4 | Macy Gray hit song |
| 56% | ITRY | 4 | Macy Gray's first and biggest hit: 2 wds. |
| 52% | ITGO | 4 | "Let ___" ("Frozen" hit song): 2 wds. |
| 51% | ICAN | 4 | "___ See Clearly Now" (1972 hit song): 2 wds. |
| 51% | ISA | 3 | "Love ___ Battlefield" (Pat Benatar hit song): 2 wds. |
| 50% | ISEE | 4 | "When Will ___ You Again" (1974 hit song): 2 wds. |
| 50% | IMTOO | 5 | "___ Sexy" (1992 Right Said Fred hit song): 2 wds. |
| 50% | THEONE | 6 | "Love ___ You're With" (1971 hit song): 2 wds. |
| 50% | ISA | 3 | "All I Need ___ Miracle" (1986 hit song): 2 wds. |
| 50% | TODO | 4 | "All She Wants ___ Is Dance" (1985 hit song): 2 wds. |
| 49% | TRY | 3 | "I ___" (2000 Macy Gray hit) |
| 48% | ATALL | 5 | "When You Say Nothing ___" (Ronan Keating's 1999 hit song): 2 wds. |
| 48% | IAM | 3 | "___ Woman," hit song by Helen Reddy: 2 wds. |
| 47% | BARRYMANILOW | 12 | "Piano man" with the hit song "Mandy": 2 wds. |
| 47% | ITBE | 4 | "Let ___," a hit song by The Beatles: 2 wds. |
| 47% | IMSO | 4 | "___ Excited" (Pointer Sisters hit song) (2 wds.) |
| 47% | ODETO | 5 | "___ Billie Joe" (1967 hit song) (2 wds.) |
| 47% | OFME | 4 | "Part ___" (Katy Perry hit song) (2 wds.) |
| 47% | IMON | 4 | "___ Fire" (Bruce Springsteen hit song) (2 wds.) |
| 47% | ONBY | 4 | "Walk ___" (Dionne Warwick hit song) (2 wds.) |
| 47% | BILLYJOEL | 9 | "Piano man" with the hit song "Piano Man": 2 wds. |
| 47% | EVERYSTORM | 10 | 2012 hit song from country singer Gary Allan: 2 wds. |
| 47% | MUSICSOUNDS | 11 | With 29-Across, hit song for 42-Across: 2 wds. |
| 47% | LONELYTONIGHT | 13 | 2014 hit song for 17- and 39-Across: 2 wds. |
| 46% | ASICE | 5 | "Cold ___" (Foreigner hit song) (2 wds.) |