| 100% | SOLES | 5 | "Diamonds on the ___ of Her Shoes" (Paul Simon song) |
| 80% | HER | 3 | "Diamonds on the Soles of ___ Shoes" (Paul Simon song) |
| 59% | PAULSIMON | 9 | He gave us "Diamonds on the Soles of Her Shoes" |
| 49% | YOURESOVAIN | 11 | Carly Simon song that was in the Top 10 on the "Billboard" Year-End Hot 100 singles of 1973 (3 wds.) |
| 47% | AXE | 3 | Weapon on the king of diamonds |
| 47% | LONELYBOY | 9 | Hit song by Paul Anka which was also used as the title of the documentary made on him: 2 wds. |
| 47% | DOCK | 4 | "(Sittin' On) The ___ of the Bay" (Otis Redding song) |
| 47% | SIZES | 5 | Numbers on the backs of bowling shoes |
| 47% | CLEATS | 6 | Spikes on the bottom of athletic shoes |
| 47% | SIZE | 4 | Number on the inside of a shoe |
| 47% | CLEAT | 5 | Spike on the bottom of a shoe |
| 47% | SOLE | 4 | Found on the bottom of a shoe |
| 47% | SCUFF | 5 | Scrape on the toes of a shoe |
| 47% | MAMMAMIA | 8 | Musical based on the songs of ABBA |
| 46% | SPIKES | 6 | Pins on the bottom of track runners' shoes |
| 46% | ANDY | 4 | Name on the bottom of Woody's shoe |
| 46% | MAMMAMIA | 8 | Musical based on the songs of 1-Across |
| 46% | MIA | 3 | "Mamma ___!" (musical based on the songs of ABBA) |
| 46% | BENHARPER | 9 | Singer of Diamonds on the Inside |
| 45% | BAY | 3 | "(Sittin' On) The Dock of the ___" (Otis Redding song) |
| 45% | RED | 3 | Signature color on the soles of Christian Louboutin shoes |
| 45% | CLEAT | 5 | Sharp item on the bottom of a golf shoe |
| 45% | MAMMAMIA | 8 | Musical based on the songs of ABBA: 2 wds. |
| 45% | GEESE | 5 | Birds given on the sixth day of Christmas, in song |
| 45% | DRUMMERS | 8 | Gifts given on the 12th day of Christmas, in song |
| 45% | OBVIOUSCHILD | 12 | *1990 Paul Simon song, with "The" |
| 44% | SOUND | 5 | "The ___ of Silence" song by Simon & Garfunkel that originally appeared on their debut album, "Wednesday Morning, 3 A.M." |
| 44% | YOUCANCALLMEAL | 14 | 1986 hit song for Paul Simon ... or an instruction from the starts of 20-, 34- and 41-Across? |
| 44% | APR | 3 | Mo. at the start of a Simon & Garfunkel song |
| 44% | TESH | 4 | John ___, composer of the "NBA on NBC" theme song |