The song is something of a lament about the physical hardships of life similar to Ol' Man River. A number of singers (such as Bing Crosby and Dean Martin) recorded the song in almost a joyful manner lacking any sentiment, which is kind of strange.
I believe the earliest recording was done by Sarah Vaughan. She recorded it twice in 1949, on January 25 and again on May 6. I'm assuming the first session was rejected which led to the second.
Later in 1949 the song was recorded by at least 6 singers with four of them achieving hit success. Frankie Laine recorded his version on June 14 and he had the biggest hit with it.
Frankie sang it kind of upbeat, but the next two versions are among my personal favorites. I'm not sure when Vaughn Monroe recorded it with his orchestra, but it hit the charts in September 1949. Vaughn's baritone voice seems well suited to the nature of the song and he used the "oh Lord" opening like Sarah and it has seldom been heard since.
Next up is the recording done by Louis Armstrong on September 6. Louis most certainly had a singing voice very well suited for songs about hardship and toil. His opening was also unique to the long history of the song.
Nine days after Louis cut the song, Frank Sinatra recorded his for Columbia Records.
Also making a splash with That Lucky Old Sun in 1949 were recordings by Bob Houston and the name of the other guy isn't coming to me at the moment.
LaVern Baker recorded it in July 1955.
Sam Cooke updated it to a late 1950's pop sound in 1957, a year after Jerry Lee Lewis rocked it for Sun Records.
The Four Esquires gave it a vocal group - light rock 'n' roll workout in 1959.
also in 1960, The Velvets gave it the pop vocal group sound
In 1961 Chuck Reed recorded it in a strictly pop style
In 1962 both The Delights and The Ecstasies did doo-wop versions in much different tempos
and a young Aretha Franklin recorded it for Columbia also in 1962
Ray Charles recorded his popular version in 1963 during his successful ABC-Paramount tenure
and in 1968 Soul legends Sam & Dave took it in a new direction (as did Solomon Burke the following year)
These are just a few examples of the various takes on the song in its early years and represents only a handful of the many recordings made. Willie Nelson had a country hit with it in 1976 and it was also recorded by country acts like Asleep at the Wheel, Tommy Cash, Tom T. Hall, Mickey Newbury and many years ago the Sons of the Pioneers.
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