When Bob Dylan described in his 1983 song “Blind Willie McTell” a “fine young handsome man” with “bootlegged whiskey in his hand,” it was almost as if he was carefully qualifying the type of bootlegging to which he was referring—the illegal production and sale of alcoholic beverages during Prohibition. The irony wasn’t lost on fans, however, when the song, withheld from the singer’s Infidels album, found its way onto various bootleg albums shortly thereafter.
With the end of Prohibition, the term was allowed to evolve into a description for unofficial or unauthorized albums of musical performances. And Dylan is usually acknowledged, more or less, as the first rock musician to be bootlegged in the late 1960s with the album Great White Wonder. However, bootlegs precede Dylan and rock music by several decades.
Private recordings of live performances can be traced to the start of the 20th century with the advent of primitive equipment like phonograph recorders on which live performances could be captured, at least in part, on discs. The proliferation of radio broadcasts after World War II also provided collectors with an abundance of material. Once these recordings were packaged into album releases, a new means of bootlegging emerged.
Jazz bootlegs have their start as early as the 1930s. An online essay, “The Story of the John Dawson Jazz Collection: The History of Private and Unreleased Live Jazz Recordings,” identifies that “the first jazz bootleg may be a radio link in a Louis Armstrong concert done in Denmark 1933. It was captured with the new technology of the time, the 78 rpm disc-cutter…”
The essay explains that “one of the early legal tests of bootleg records in the USA occurred in 1936. This happened when transcription recordings made off the air were so good that small radio stations could compile programs by Bing Crosby or Paul Whiteman and sell them to the public as records.”
What is possibly the most famous jazz bootleg is a performance by Duke Ellington and his band at the Crystal Ballroom in Fargo, North Dakota on November 4, 1940. Recorded by two college students, Richard Burris and Jack Towers, the recording was made with the permission of Ellington, the venue’s owner and the William Morris Agency with the provision that it could not be used for commercial purposes.
Using several microphones and “a sapphire-tipped cutter that carved v-tracks in 16-inch acetate discs,” Burris and Towers “cut 5 1/2 discs, 15 minutes per side,” the essay reports.
Towers explained that he dubbed a tape copy of the show for someone years later. That copy wound up in the hands of someone else and eventually an LP of the performance appeared in Europe in 1964 with CD releases decades later.
As for classical music, the 1994 book Bootleg informs us, “the bootlegging of operatic performances continued to generate the largest area of growth in the decade before rock bootlegs…” Steven E. Jones is identified as the person “who began the commercial bootlegging of operas in earnest…” using “acetate air-checks” of 1930s and 1940s radio broadcasts.
Bootleg also identifies Roland Ernest, who “seemed able at will to obtain high-quality recordings of any Carnegie Hall concert he so desired.” It seems his “greatest coup was perhaps the most famous opera bootleg of them all: [Spanish soprano Montserrat] Caballe’s American debut in Donizetti’s Lucrezia Borgia.”
Over the years, bootleg albums have lost their outlaw status, largely due to MP3s rendering them unnecessary. Director Peter Jackson has discussed his use of Beatles bootlegs of the Get Back sessions as research for his documentary of the same name. Artists like Frank Zappa and, more recently, Neil Young have officially released some of their formerly unauthorized albums. Columbia Records initiated a Bob Dylan Bootleg Series 30 years ago and followed it with a Miles Davis Bootleg Series. And Ellington’s 1940 Fargo performance received an official release and a Grammy Award.