The next prompt is “A song from the year you were born.” Now, THAT is a nicely specific framework. I know at least two people born in 1966 who know WAY more about the music of the year they were born than I do about 1953. I suppose it’s because I was born in the “pre-rock era.”
There are tons of titles I recognize that were performed by others. Ebb Tide, an instrumental by Frank Chacksfield (#2); Your Cheatin’ Heart – Joni James (#2); P.S. I Love You – the Hilltoppers (#4). Cryin’ in the Chapel – June Valli (#4) and several others.
Most of the ones I know, I own on a compilation disc someone gave me for my birthday about a decade ago.
(How Much Is) That Doggie in the Window? – Patti Page, #1 in March. My mother would reference this song when I was a child.
You, You, You – Ames Brothers, #1 in September. One may remember Ed Ames from the Daniel Boone TV show in the mid-1960.
Don’t Let the Stars Get in Your Eyes – Perry Como, #1 in January. Como had a variety show that started before I was born and lasted until 1963. I saw it occasionally.
Eh, Cumpari! – Julius La Rosa, #2 in November. LaRosa was famously fired by Arthur Godfrey that year.
Rags to Riches – Tony Bennett, #1 in November. Bennett had a “comeback” in 1993 and is still performing.
Istanbul Not Constantinople – the Four Lads, #10 in December. I heard the They Might Be Giants version from 1990 first. I have this on a Cadence Records compilation; that was the label of the Everly Brothers, among others.
Santa Baby – Eartha Kitt, #4 in December. I answered a Quora question about this: Who originally recorded and sang “Santa Baby”? Eartha Kitt, one of the women who played Catwoman on the TV show Batman in the 1960s. I have the track on an album called Billboard Greatest Christmas Hits 1935–1954, which came out in 1989… But the first version I heard was by Madonna on the original A Very Special Christmas from 1987.
Crying in the Chapel – the Orioles, #11 in September, #1 for five weeks on the Rhythm and Blues charts. The disparity between the pop and RB chart action partly explains why various charts exist.