| SYMS | "___ by Sinatra" (1982 collaborative jazz album) |
| NIGHTANDDAY | Cole Porter tune recorded by Sinatra |
| REPRISE | Record company started by Sinatra |
| TENANCY | Possession of musical note by Sinatra? (7) |
| MOONRIVER | Song sung by Sinatra (4,5) |
| FEDORA | Wide-brimmed hat often sported by Sinatra |
| TRIOSONATA | Piece for classical musicians performed by Sinatra too |
| MILKYWAY | Stars, the sort that interrupt song by Sinatra (5,3) |
| GNATSLIFE | Shortest song ever recorded by Sinatra? |
| ITSNOTEASY | 'Hip hop' song performed by Sinatra, Lena Horne et al. |
| OCEAN | Surname of heist masterminds played by Sinatra, Clooney, and Bullock |
| DAMONE | Crooner admired by Sinatra |
| HERBIEHANCOCK | American keyboardist whose album River: The Joni Letters won the 2008 Grammy Award for Album of the Year, only the second jazz album ever to win the award |
| BLUE | Kind Of ___, 1959 jazz album by Miles Davis (4) |
| ARCADE | 'Penny --', a jazz album by Joe Farrell (6) |
| SWISSMOVEMENT | Grammy-nominated 1969 live jazz album by Les McCann and Eddie Harris |
| ELLA | "Billie, ___, Lena, Sarah" (compilation jazz album) |
| OLE | "___ Coltrane" (1961 jazz album) |
| SATCH | "___ Plays Fats" (1955 jazz album) |
| UNIQUE | 1956 jazz album "The ___ Thelonious Monk" |
