"The Gypsy" (also spelled "The Gipsy") is a popular song composed by Billy Reid, a British bandleader, and introduced in 1945 with a recording by Reid's orchestra featuring vocalist Dorothy Squires. The song achieved major commercial success in the United States in 1946, when recordings by both Dinah Shore and the Ink Spots reached number one on the Billboard chart on the same day, making it one of the biggest pop hits of its era. The Ink Spots' version was also featured in a 1946 Soundie short film. While the song originated as a pop composition rather than a jazz standard, it attracted notable jazz interpretations. Louis Armstrong recorded it in 1953 for Decca in New York City with The Commanders, and it became a personal favorite of Armstrong's, who chose it for the session and performed it frequently in live settings through 1956. The tune represents a characteristic example of the mid-1940s pop repertoire that crossed over into jazz performance, with its melody and changes providing material for jazz musicians to reinterpret in their own idiom.
