| TONYROME | Frank Sinatra, in 1967 |
| THREE | "Which one will the fountain bless?" asked Frank Sinatra in the Oscar-winning song, ... Coins In The |
| TONY | 1967 crime film starring Frank Sinatra in the title role (4,4) |
| MYWAY | Hit for Frank Sinatra in 1969 and again in 1994 (2,3) |
| DOBEDOBEDO | Nonsense line sung by Frank Sinatra in "Strangers in the Night" |
| ROME | 1967 crime film starring Frank Sinatra in the title role (4,4) |
| TOSSED | "I was lost; The losing dice were ...; My bridges all were crossed; Nowhere to go," sang Frank Sinatra in Just In Time |
| MIAFARROW | Actress who married singer Frank Sinatra in 1966 |
| HOPES | Oscar-winning song that was made famous by Frank Sinatra in 1959, High ___ (5) |
| REPRISE | American record label founded by Frank Sinatra in 1960 (7) |
| ALLTHEWAY | Song recorded by Frank Sinatra in 1957 (3,3,3) |
| DETROIT | Character played by Frank Sinatra in 1955 musical Guys and Dolls, Nathan ---- (7) |
| THATSLIFE | Song whose most famous version was released by Frank Sinatra in 1966 (5,4) |
| LIOTTA | Actor Ray ___ who played Frank Sinatra in the 1998 film "The Rat Pack" |
| BONO | He duetted with Frank Sinatra in 1993 on "I've Got You Under My Skin" (4) |
| STRANGERSINTHENIGHT | Number One hit for Frank Sinatra in 1966 (9,2,3,5) |
| WHICHIM | "And now, the end is near; And so I face the final curtain; My friend, I'll say it clear; I'll state my case, of ... certain," sang Frank Sinatra in My Way (5,1'1) |
| TOMENTION | "Regrets, I've had a few; But then again, too few ...; I did what I had to do; And saw it through without exemption," sang Frank Sinatra in My Way (2,7) |
| TOBENEARYOU | "Happy ...; When you need someone to cheer you; All the way," sang Frank Sinatra in 1957 (2,2,4,3) |
| IHADTODO | "Regrets, I've had a few; But then again too few to mention; I did what ...; And saw it through without exemption," sang Frank Sinatra in My Way (1,3,2,2) |
