(Copy and Paste URL for songs you want to listen to--sorry :O)
The list of great singers is endless and I tend to favor those who were known before 1960 and mostly those referred to as balladeers. Of the singers and songs listed below the latest of the recordings was in 1966.
Like many listed above Sinatra first found fame in the 1940s and it would be hard to pick just one song of his to represent the singer because he had so many hits but the one I picked by him was a big hit when I was 30 and about to go a big change in my life.
All the songs, and singers, bring back memories, mainly in the 1950s as I came out in New York City and each one brings back many memories!
1) Frank Sinatra “Strangers In The Night” 1966 https://youtu.be/BTOeRwIUnG0
2) Tony Bennett “Boulevard of Broken Dreams” 1957 https://youtu.be/jBesLqgs4yA
3) Johnny Ray “Cry” 1951 https://youtu.be/5FO07LN72ek
4) Mel Torme “The Christmas Song” 1950 Though made more famous by Nat King Cole Torme wrote this song so---- https://youtu.be/8fxmh9srt1w
5) Eddie Fisher “Wish You Were Here” 1953 https://youtu.be/OPkEdMAFT00
6) Frankie Laine (One of my brother’s favorite singers--drove me crazy with “Mule Train” but I did like this one) “Black And Blue” 1946 https://youtu.be/23ccsC7UTOE
7) Vic Damone “We Kiss In A Shadow” 1958 from “The King and I” a Gay anthem https://youtu.be/xBBaCxxyBt0
8) Johnny Mathis “It’s Not For Me To Say” 1957 https://youtu.be/xBBaCxxyBt0
9) Billy Eckstine “My Foolish Heart” 1950 from one of my favorite movies https://youtu.be/tNTVqFUQxi4
10) Harry Belafonte “Day O” aka “Banana Boat Song” 1956 https://youtu.be/6Tou8-Cz8is
11) Nat King Cole “Unforgettable” 1951 https://youtu.be/JFyuOEovTOE
12) Al Martino “An Affair To Remember” 1957 Another favorite movie https://youtu.be/6EHGoJVeBK0
13) Perry Como “If (They Made Me A King)” 1951 https://youtu.be/jQvW1M7K6II
14) Tony Martin “Stranger In Paradise” 1954 https://youtu.be/rXJM_ZeMs1g