The Gypsy

This article was originally published as part of a  “British Invasion” edition of our online magazine.   We elected to feature a tune imported from the U.K. that is so solidly established as a “standard,” few people are aware that it is not an American song.

“The Gypsy” was penned by British orchestra leader Billy Reid, who developed the tune as a showpiece for his mercurial vocalist, Dorothy Squires. Squires could be described as a Welsh version of Dinah Shore, but only if you somehow crossed Dinah with Mae West. Unfortunately Squires is best remembered for robbing the cradle when she married a young Roger Moore, and then making his life miserable by denying him a divorce for years and years. She then became something of a lampoon of herself, scoring minor hits with songs like “My Way” in the 1970s.

Squires was in fact one of England’s finest torch singers of the 1940s and early 1950s. She sang the original versions of three Reid songs that would go on to be considered standards in the Great “American” Songbook; in addition to “The Gypsy,” these were “A Tree in the Meadow,” and “I’m Walking Behind You.” “Tree” was a number one hit for Margaret Whiting in 1948, and “Walking” hit the top spot for Eddie Fisher in 1953.

Incidentally, “I’m Walking Behind You” contributes an interesting footnote in the history of American pop. Penned by Reid and recorded by Squires, the song was rising up the British charts when it was brought to Frank Sinatra to record. He did so, but unfortunately Eddie Fisher recorded and released the song within a few days of Sinatra’s version. In 1953 Sinatra still had significant star power, however his music career was in a slide while Fisher’s was rocketing skyward. “Walking” had by now fallen off the British charts, but Fisher’s version breathed new life into the song, and it topped the charts in both the USA and UK.

Back to “The Gypsy.”

Written in England in 1945, the song was recorded by Squires with a medium, uptempo beat. It did very little in the USA. Competing versions were recorded in March, 1946 by The Ink Spots and by Guy Lombardo — both on the Decca label. It was common at the time for various labels to have competing “group” versions, “female” versions, “male” versions, “black” versions, etc. to provide product for various musical tastes. In this case, Decca covered almost all the bases, as the Lombardo version featured a vocal by cabaret star Hildegarde (Hildegarde Loretta Sell). Other, less prominent artists also rushed out versions in March, none of which made much noise on the charts. The only notable version among these was probably Louis Prima’s. Decca’s recordings featured more or less the same arrangement — much slower than Squires’ original. This slow ballad became the norm for “The Gypsy,” even though Reid probably didn’t consider the ultra slow tempo.

The Lombardo version was largely regarded as a musical miss, and Columbia saw an opportunity to rush out a more polished vocal by Dinah Shore. RCA wanted in, and put out a male vocal version by Sammy Kaye featuring Billy Williams at the microphone.

By May of 1946 a few of the recordings began to climb the charts. Shore’s version received a lot of mainstream airplay. Working with bandleader Sonny Burke, Dinah’s approach may be one of the most letter-perfect vocal performances of the 1940s. Burke — speaking of footnotes — would eventually become one of the musical directors for Sinatra’s Reprise label.

It was the first U.S. recording, made by the Ink Spots, that would dominate most markets. Featuring a rich harmony and noted for complex chord progressions, the Ink Spots had by 1945 taken the lead in a style that had previously been dominated by the Mills Brothers. The Mills would take charge again in 1950, but in 1946 the Inks ruled. The song entered the Billboard charts in May, peaked at number one, and stayed on the charts for an incredible four months.

Dinah’s version was no slouch, reaching number two — just below the Ink Spots. It stayed on the charts more than three months. It actually might be considered the more impressive single, as the flip side “Laughing on the Outside (Crying on the Inside)” reached number three at the same time. So while the Ink Spots had the top recording, if we consider Shore’s other hits, it must be noted that Dinah ruled the airwaves more than any other artist in 1946.

Sammy Kaye’s effort was a couple weeks late in the sweepstakes; it managed to hang on for a month and peaked at a respectable number seven. “The Gypsy” was easily the dominant song of 1946, predating the much more well known “British Invasion” by almost two decades.