"The Gypsy in My Soul" is a popular song written for the 50th anniversary of the University of Pennsylvania Mask and Wig show in 1937 by two Penn graduates, Clay Boland and Moe Jaffe.^[1] Boland wrote the music and Jaffe the lyrics. Although both men had long since graduated, it had become the practice at the time for professionals, rather than students, to compose songs for the show.

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Although the song did not become a big hit at the time it was written, it has become a classic over the decades, particularly in the jazz repertoire, as it has been recorded by over 100 artists.^[2]