| 100% | SLIP | 4 | Paul Simon hit song "___ Slidin' Away" |
| 67% | SLIP | 4 | "___ Slidin' Away," 1977 hit song by Paul Simon ... or what may happen while walking on an icy road |
| 60% | SLIP | 4 | Paul Simon's "___ Slidin' Away" |
| 49% | NINEPOUNDSTEEL | 14 | Joe Simon hit song |
| 49% | YOUBELONGTOME | 13 | Carly Simon hit song |
| 48% | YOUCANCALLMEAL | 14 | 1986 hit song for Paul Simon ... or an instruction from the starts of 20-, 34- and 41-Across? |
| 47% | GRACELAND | 9 | Paul Simon hit with Ladysmith Black Mambazo vocals |
| 46% | CAN | 3 | "You ___ Call Me Al," Paul Simon hit |
| 46% | VAIN | 4 | "You're So ___" (Carly Simon hit song) |
| 46% | SLIDIN | 6 | Paul Simon's "Slip ___ Away" |
| 45% | HOMEWARDBOUND | 13 | Hit song by Simon and Garfunkel |
| 45% | AMA | 3 | Paul Simon song "I ___ Rock": 2 wds. |
| 44% | YOUCANCALLMEALLY | 16 | Paul Simon song about a budding international union? |
| 44% | OBVIOUSCHILD | 12 | *1990 Paul Simon song, with "The" |
| 43% | JULIO | 5 | Schoolyard pal in a Paul Simon song |
| 43% | JULIO | 5 | Schoolyard character in a Paul Simon song |
| 40% | CAN | 3 | "You ___ Call Me Al," Paul Simon hit that features in season 5 of "The Office" |
| 40% | MRS | 3 | Simon & Garfunkel hit song "___ Robinson" |
| 39% | HOMEWARDBOUND | 13 | Simon and Garfunkel hit song |
| 38% | CALLMEAL | 8 | Song on Paul Simon's 7th album, You Can __ |
| 37% | ESCAPADE | 8 | Janet Jackson hit song with the lyric "Come on baby, let's get away" |
| 37% | EDIE | 4 | Singer Brickell (married to Paul Simon) whose biggest hit was 1988's "What I Am" |
| 37% | IROCK | 5 | Boast formed by removing the middle two words of a popular Paul Simon song title |
| 36% | CALL | 4 | "You Can ___ Me Al," 1986 Paul Simon hit inspired by a party where he was mistakenly referred to as "Al" |
| 36% | BLOWININTHEWIND | 15 | Bob Dylan song that was a #2 hit for Peter, Paul & Mary |
| 35% | SAYSAYSAY | 9 | Paul McCartney/Michael Jackson hit song (3 wds.) |
| 35% | LIES | 4 | "Love ___," hit song by Khalid and Normani which is a part of the soundtrack for "Love, Simon" |
| 35% | POPCHARTTOPPER | 14 | Hit song |
| 35% | SINGLE | 6 | Hit song |
| 35% | LONELYBOY | 9 | Hit song by Paul Anka which was also used as the title of the documentary made on him: 2 wds. |