| 100% | COME | 4 | "___ Fly With Me" (classic Frank Sinatra song) |
| 64% | OLDNEWYORK | 10 | Locale in a classic Frank Sinatra song |
| 62% | THEMOON | 7 | Fly Me to __, Frank Sinatra's song request |
| 57% | MYWAY | 5 | Classic Frank Sinatra song that begins, "And now, the end is near" (2 wds.) |
| 54% | WAY | 3 | "My ___" (classic Frank Sinatra song) |
| 53% | THELADYISATRAMP | 15 | Frank Sinatra song with the lyric "Won't go to Harlem in ermine and pearls" |
| 52% | MOON | 4 | "Fly Me to the ___," 1964 song by Frank Sinatra with the Earth's natural satellite in its title |
| 51% | NEWYORK | 7 | With 42-Across, Frank Sinatra signature song |
| 49% | WITCHCRAFT | 10 | Frank Sinatra song |
| 49% | LUCKBEALADY | 11 | Frank Sinatra song |
| 46% | HOPES | 5 | "High" feelings of a Frank Sinatra song |
| 45% | MOON | 4 | With 6-Across, classic song with the lyric "Wherever you're goin', I'm goin' your way" |
| 45% | CAHN | 4 | "Come Fly with Me" lyricist Sammy |
| 45% | CAHN | 4 | “Come Fly with Me” lyricist Sammy |
| 45% | LARK | 4 | Flier with elaborate songs |
| 45% | PERU | 4 | Country mentioned in Sinatra's "Come Fly With Me" |
| 44% | ESOBESO | 7 | Classic song with the lyric "I love your kiss" |
| 44% | HANG | 4 | "___ With Me" (Robyn song) |
| 44% | MOUNTAINHIGHVALLEYLOW | 21 | Classic song with the repeated line "If you need me, I will be nearby" ... shown symbolically in this puzzle |
| 44% | STYLE | 5 | Taylor Swift song with the lyric "And I got that red lip classic thing that you like" |
| 43% | COPA | 4 | Frank Sinatra's "Meet Me at the ___" |
| 43% | FLY | 3 | Frank Sinatra's, "___ Me To The Moon" |
| 43% | BABYBLUES | 9 | Frank Sinatra broke hearts with these eyes |
| 42% | MYWAY | 5 | Classic Sinatra song |
| 42% | ODNIGHTIRENE | 12 | Classic song with the lyric "I'll see you in my dreams" |
| 42% | LOUIE | 5 | When repeated, classic song with the lyric "Me gotta go" |
| 42% | MOON | 4 | "Fly Me to the ___," Frank Sinatra melody that was closely associated with NASA's Apollo space program |
| 42% | ADELAIDESLAMENT | 15 | Classic Frank Loesser song from a 1950 musical |
| 42% | COME | 4 | "___ Away With Me," Norah Jones' song |
| 42% | BIRTHOFTHEBLUES | 15 | Sinatra classic, with "The" |