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It is sung from the viewpoint of a woman enamored of a man whom she finds to be an exceptional lover, even better than Romeo:
The song was introduced by the legendary singing comedian Eddie Cantor who recorded it for Columbia Records in 1924. It was recorded by several of his contemporaries, including Billy Murray. Murray's version is wrapped inside a lively instrumental that is clearly intended for dancing the Charleston or other popular Jazz Age dances. Murray's version featured a short instrumental interlude between the two sets of verses, which included a bar from an earlier Murray recording with a similar theme, also introduced by Eddie Cantor:
In 1949, "Charley" was recorded on the Decca Records label by the Andrews Sisters as the A-side of a single which had "She Wore A Yellow Ribbon" (from the popular 1949 John Wayne movie of the same name) as the B-side. It was also one of two theme songs used by the popular radio program The Spike Jones Show.
It is now most easily found as a square dance tune, with at least three different publications, two by MacGregor and one by Hi Hat Records, the latter using the alternate spelling and punctuation "Charlie, My Boy." Several of the old versions, including the performance by Billy Murray, are available on YouTube.