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Though the song's title is grammatically incorrect, the phrase my shadow and I somehow does not have the same ring to it. "Me And My Shadow" is described by The Tin Pan Alley Song Encyclopedia
as the "quintessential soft-shoe number, a masterpiece of restrained melody that practically dances all by itself". Author Thomas Hischak says it was written by Billy Rose, dates from 1927, and was associated with band leader Ted Lewis who sang it as he conducted his orchestra, and kept it in his repertoire for years. In the 1950s it was revived by Pearl Bailey, and appears in a number of films including the 1975 Funny Lady
where it is sung by James Caan as Rose himself.
The song's title suggests it is a fairly light-hearted take on loneliness, disappointment, or perhaps a failed date. A long time standard, this is a classic duet, and has been performed and recorded many times as such, including by Morecambe & Wise, whose 1961 single (recorded with their usual frivolity) on the HMV label was the B Side of "We're The Guys (Who Drive Your Baby Wild)".
Here it was credited to Rose, Jolson and Dreyer; the sheet music has been credited variously as Music by Billy Rose, Words by Al Jolson; and Words and Music by Dave Dreyer, Billy Rose and Al Jolson. It seems likely that Rose wrote the lyrics only, or most of them, and they were amended or adapted by the singer, Jolson; Dave Dreyer was an established composer who went on to become head of music at RKO Radio.
"Me And My Shadow" is the sort of song that lends itself readily to parody; a somewhat off-beat version (with amended lyrics) was recorded by Robbie Williams and Jonny Wilkes.
The song's title has not unnaturally become a cliché, and has been used for a 1947 three act play by Bruce Abbott, for a book about fighting cancer, and another about living with multiple sclerosis. (thanks, Alexander Baron - London, England, for all above)