"Maggie May" expresses the ambivalence and contradictory emotions of a boy involved in a relationship with an older woman and was written from Stewart's own experience. In the January 2007 issue of Q magazine, Stewart recalled: "Maggie May was more or less a true story, about the first woman I had sex with, at the 1961 Beaulieu Jazz Festival." The woman's name was not "Maggie May"; Stewart has stated that the name was taken from "an old Liverpudlian song about a prostitute."
The song was recorded in just two takes in one session. Drummer Micky Waller often arrived at recording sessions with the expectation that a drum kit would be provided and, for "Maggie May", it was – except that no cymbals could be found. The cymbal crashes had to be overdubbed separately some days later.
The song was released as the B-side of the single "Reason to Believe", but soon radio stations began playing the B-side and "Maggie May" became the more popular side. The song was Stewart's first substantial hit as a solo performer and launched his solo career. It remains one of his best-known songs.
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