"The Gypsy in My Soul", a popular song, was 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. Boland wrote the music, 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.
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. It continues to be recorded today, with a notable recent recording by Connie Evingson (2005).
A sample of other recordingsLouis Armstrong
Mildred Bailey with Red Norvo's Orchestra recorded on December 19, 1945 and released on Crown 104
Charlie Byrd - instrumental
Rosemary Clooney - At Long Last (with the Count Basie Orchestra) (1998)
Sammy Davis, Jr. with orchestra conducted by Jack Pleis recorded on August 3, 1956 and released on Decca.
Doris Day with orchestra conducted by Paul Weston recorded in 1956 and released on the Columbia album Day by Day
Ella Fitzgerald on her Verve release Get Happy!
Oscar Peterson - instrumental
Andre Previn - instrumental
Bud Shank and Bob Cooper - instrumental
Jeri Southern The Dream's on Jeri (1998)
Jo Stafford with the Art Van Damme Trio recorded on September 30, 1956 and released on the Columbia album Once Over Lightly
Margaret Whiting with Frank DeVol's Orchestra recorded December 23, 1947 and released on Capitol 15038
Lester Young, Roy Eldridge & "Sweets" Edison - instrumental