Music History

The Secret History of Bootleg Records

I confess: I used to buy a lot of bootleg CDs. And I mean a lot. They ran the gamut: live recordings, discs full of outtakes and alternate versions, reissues of long-gone early recordings from artists and plenty of CDs containing nothing but demos.

I found treasures at indie record stores, record shows, on eBay and in far-flung countries (Indonesia and Malaysia were very good for a long while.) The best came from labels like KTS and TMOQ, companies that prided themselves on delivering the best audio quality and were worth the $30, $40 and $50 I paid.

I have a few vinyl bootlegs, too–mostly live material from Zeppelin, Bowie and the Stones–and I still run across them at record fairs.

The Internet has pretty much killed the physical bootleg. The owner of a Caribbean record store who sold me dozens of discs (including some awesome Oasis and Smashing Pumpkins stuff) several years ago lamented “I can’t get them anymore from anywhere!” The last time visited his shop, he had nothing. I haven’t been back to see him in several years.

But bootlegs continue to fascinate collectors and the hardcore music fan who has everything. takes a look at the history of these wonderful but highly illegal musical documents.

In 1994, British rock writer Clinton Heylin published Bootleg: The Secret History of the Other Recording Industry, an entertaining history of the illicit form. Tracing the line from the emergence, in 1969, of a bunch of home and live tapes of Bob Dylan, sold in a plain white sleeve rubber-stamped with the title Great White Wonder, on through the likes of Prince’s Black Album (“probably the best-selling bootleg of all time,” wrote Heylin) and then-superstars R.E.M. and U2, Heylin paints an amusing portrait of bootlegging’s squirrelly practitioners: “Bootlegging, by its very nature, qualifies as disorganized crime … there was never a conspiracy, or a ‘Mr. Big,’ just people operating in the twilight zone of insatiable demand for a lot of pleasure and a modicum of profit.” He quotes bootlegger Lou Cohan: “The figure they gave at the time of my 1976 bust, like they confiscated 250 million dollars’ worth of bootlegs, is totally ridiculous. I was manufacturing 2,500, 3,500, at the most 4,000 of a particular bootleg of a particular artist and selling them wholesale … at the most for $1.50 each.”

But even as Heylin’s book was coming out, its subtitle was already becoming outdated: Starting in the the late ’80s and accelerating into the ’90s, the cornucopia of CD reissues and box sets pioneered by labels like Rhino were powered as much by rarities and outtakes as cleaned-up versions of old albums and singles: The 1984 Elvis Presley six-LP Elvis — A Golden Celebration was heavy on previously unreleased material, as was Bob Dylan’s three-CD Biograph a year later. It’s no coincidence that Presley and Dylan are two of the most heavily booted artists of all time, with a plethora of unreleased studio sessions as well as widely traded live shows. Today, Presley’s vaults have been thoroughly exhumed by RCA, including plenty of material aimed straight at the collectors who eat up bootlegs. And of course, Dylan’s originally unreleased back pages have been part of the official public record since 1975, when he and the Band’s Basement Tapes first saw legal light as a two-LP set.

Today, the very idea of a bootleg — outtakes and live recordings on typically shoddy pressings that cost, in many cases, twice the price of a regular album — has long been quaint in an era where so much is available for free online, “official” or not. Here are 25 notable boots from the LP and CD eras, in chronological order.

Keep reading.

Alan Cross

is an internationally known broadcaster, interviewer, writer, consultant, blogger and speaker. In his 40+ years in the music business, Alan has interviewed the biggest names in rock, from David Bowie and U2 to Pearl Jam and the Foo Fighters. He’s also known as a musicologist and documentarian through programs like The Ongoing History of New Music.

Alan Cross has 38321 posts and counting. See all posts by Alan Cross

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