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There are 26 clues with the answer 'TONYBENNETT'
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CLUE
1.
Grammy-winning vocalist
2.
Classic vocalist who served in the U.S. Army
3.
This 95-year-old singer received five nominations, for duet work with Lady Gaga
4.
Frank Sinatra School of the Arts co-founder
5.
American singer born Anthony Dominick Benedetto in 1926
6.
U.S. jazz vocalist born in 1926 whose signature song is I Left My Heart in San Francisco (4,7)
7.
Crooner who sang a duet with Lady Gaga on the standard Cheek to Cheek at the 2015 Grammys: 2 wds.
8.
Rags to Riches singer who won the 2017 Library of Congress Gershwin Prize for Popular Song: 2 wds.
9.
He left his heart . . .
10.
"Rags to Riches" singer [Broadway]
11.
Crooner who made a duet album with Lady Gaga in 2014 (4,7)
12.
American singer associated with the song I Left My Heart in San Francisco (4,7)
13.
This crooner won the Gershwin Prize in 2017 at the age of 91
14.
Skeletal principle, commented Spooner of the famous crooner (4,7)
15.
I Left My Heart in San Francisco singer who's an accomplished painter: 2 wds.
16.
2018 AP Coach of the Year who shares his name with the singer of I Left My Heart in San Francisco: 2 wds.
17.
Broadway Theatre Award winner, judging by his name
18.
Singer (WWII rifleman)
19.
Venerable crooner
20.
Crooner who began his career performing as Joe Bari
21.
"Rags to Riches" singer
22.
Singer who released the album "Love for Sale" at the age of ninety-five
23.
He recorded the 2021 album "Love for Sale" with Lady Gaga
24.
Legendary jazz singer died at age 96 in July (4,7)
25.
"I Left My Heart in San Francisco" singer (1926-2023)
26.
US singer who collaborated with Lady Gaga on the 2014 album Cheek to Cheek (4,7)