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St. James Infirmary Blues" is based on an 18th century traditional English folk song called "The Unfortunate Rake" (also known as "The Unfortunate Lad" or "The Young Man Cut Down in His Prime"), about a soldier who uses his money on prostitutes, and then dies of a venereal disease. Variations typically feature a narrator telling the story of a young man "cut down in his prime" (occasionally, a young woman "cut down in her prime") as a result of morally questionable behavior. For example, when the song moved to America, gambling and alcohol became common causes of the youth's death. There are numerous versions of the song throughout the English-speaking world. It evolved into other American standards such as "The Streets of Laredo."[1]
The title is derived from St. James Hospital in London, a religious foundation for the treatment of leprosy. It was closed in 1532 when Henry VIII acquired the land to build St. James Palace.[2]
The song was first collected in England in its version as "The Unfortunate Rake" by Henry Hammond by a Mr. William Cutis at Lyme Regis, Dorset in March 1906.

"How High the Moon" is a jazz standard with lyrics by Nancy Hamilton and music by Morgan Lewis. It was first featured in the 1940 Broadway revue Two for the Show, where it was sung by Alfred Drake and Frances Comstock.[1]

In "Two for the Show", this was a rare serious moment in an otherwise humorous revue. The song was sung, in a slow fox trot tempo, by a group of evening-dressed people walking along a London street. At the end, they all looked at the sky, and cowered, obviously terrified: quick curtain. It was 1940, and the time of the London blitz: a clear night meant "bomber's moon".

The earliest recorded hit version was by Benny Goodman & His Orchestra. It was recorded February 7, 1940 and released by Columbia Records as catalog number 35391, with the flip side "Fable of the Rose".[2] The Les Paul Trio recorded a version released as V-Disc 540B with a spoken introduction which was issued in November, 1945 by the U.S. War Department. In 1948, bandleader Stan Kenton enjoyed some success with his version of the tune. The recording, with a vocal by June Christy, was released by Capitol Records as catalog number 911 (with the flip side "Willow, Weep for Me")[3] and 15117(with the flip side "Interlude").[4] It reached the Billboard magazine Best Seller chart on July 9, 1948, its only week on the chart, at #27.[5]

The best-known recording of the song is by Les Paul and Mary Ford, made on January 4, 1951.

The record was released by Capitol Records as catalog number 1451, with the flip side "Walkin' and Whistlin' Blues",[6] and spent 25 weeks (beginning on March 23, 1951) on the Billboard chart,[5] 9 weeks at #1. The record was subsequently re-released by Capitol as catalog number 1675, with "Josephine" on the B-side.[7]