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What music's outsiders and oddballs got up to before the Internet

A new coffee-table book and CD set documents the weird bygone world of private-press records.

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In 2002 sample master DJ Shadow released his second full-length, Private Press, but I didn't get the reference in the title till a few years later. In the mid-aughts, obscure private-press albums that had been fetching ridiculous prices from rabid record collectors—Red Hash by Gary Higgins, You Think You Really Know Me by Gary Wilson—were reissued in a steady stream.

"Private press" originally described the publishing of books as limited-­edition art objects, as opposed to commercial publishing. But in music, a private-­press record was more commonly a vanity pressing, self-financed and self-released often for no other reason than to memorialize or commemorate something. They had virtually no distribution and could rarely be found outside the region where they were produced.

Perhaps the most famous private-press album is Philosophy of the World by the Shaggs, a truly confounding band formed in 1968 when three sisters from a New Hampshire family were "encouraged" to play rock music by their father, Austin Wiggin, who became their manager. It's been reissued several times since 1980 and recognized as a cult classic for decades. In 2006 the New York Times ran a feature on the growing interest in private-press records, mentioning the Higgins reissue (on Drag City, which has stayed in the business of private-press reissues ever since) and the sleuthing efforts that the Numero Group and Gear Fab were devoting to impossibly rare vinyl with virtually no paper trail.

DJ Shadow found most of the samples he used for his early albums on private-press releases, which meant that hardly anyone would be able to figure out their provenance—a common enough approach in the world of hip-hop. But it's one thing to value a record because it's got a couple of hot breakbeats that nobody in the universe will recognize, and another thing entirely to actually like listening to it top to bottom.

There have been thousands upon thousands of private-press records, and only a few are indisputably accomplished pieces of art by musicians who simply didn't have the good fortune to find a label to release them. Most are borderline unlistenable, at least when judged by traditional criteria, and were pushed out into the world by artists who were apparently tone deaf, deluded, or both. The Times article, unsurprisingly, is mostly about the former: "Many of these records have been around for a while, at record fairs and so on," says music writer and collector Byron Coley. "Lots of collectors initially bought the private-press records strictly for their covers. They were fetish objects in a way. Then people started to listen to them, and realized, hey, there's some great songs on these records. What's happened is that younger listeners have picked up on it, and that has created renewed interest in the CD reissues."

But tragically overlooked treasures aren't by and large the records featured in the gigantic new coffee-table book Enjoy the Experience: Homemade Records 1958-1992 (which comes with a download coupon for two CDs' worth of music). Published by Sinecure and assembled by collectors Johan Kugelberg, Michael P. Daley, and Paul Major, it focuses on the weirdos and oddballs on the fringe—though in the case of private-press records, there were far more people on the fringe than anywhere else. Because some of these musicians can seem lost or damaged, appreciating their output is often a delicate proposition. In the book's introduction Kugelberg writes, "Enjoying these albums is not savant-driven. It is not an ironic spectator sport." He adds, "The music stands on its own." Well, sometimes it does.

The bulk of the 508-page hardcover is devoted to the sort of album covers that caught the eyes of the early collectors Coley describes—and their varying combinations of amateurish design, naked cliche, and utter strangeness are often endearing. Welcome by St. Therese's Folk Group features crude silhouettes of longhairs playing a drum kit and a guitar; a third figure hangs from a cross, the outline of his crown of thorns making it look eerily like he has horns. On the next page is the sleeve of a seven-inch by the Happy Eggs, which pictures all three mustachioed members laughing in candid shots that have been cropped into ovoids somewhere between eggs and cameo frames.

The cover images make the book worth the price for me—I spent hours with them. There's a section devoted to bands from elementary and high schools, plus a large assortment from artists who used the templates offered by Century Records, where cover after cover uses the same image—crashing waves with an eagle soaring overhead, an illustration of pinwheel-like flowers, a blank movie-theater marquee—and only the text at the top changes. Otherwise the editors barely try to categorize anything; the variety is so sprawling that their efforts would be pointless.

Enjoy the Experience opens with a lengthy interview with Major, who in the mid-80s was one of the earliest private-press collectors (and currently plays guitar and sings in Endless Boogie). It also includes more than a hundred record reviews, many by Major, and dozens of artist profiles. "What I like about some of these private pressings and why I'm so personality-driven with them is that you start imagining what these people's lives are like," Major says. "You extend out and you make a little movie in your mind about these people that you get really from just the sound and the few images or the look of the cover."

Most of the profiles are written by Daley, whose prose can make even the most colorful folks sound a little dull. (Other contributors, notably Rich Haupt, approach their subjects with more personality and humor.) Daley frequently makes illogical leaps, and he seems too eager to pack in the odd details he's discovered in his research—their relevance often isn't clear. Take for example this passage about Chicagoan Harriette Blake, an acrobat and lounge singer described as "tabbed for stardom" by Sun-Times columnist Irv Kupcinet: "An 1890s-themed beer garden was set up for the 3rd Madison Realtors Home Show in the spring of 1969. The garden housed Blake and magician/comedian Don Alan who entertained the heavily trafficked summit, while mini-skirt clad Futura, a robot girl, was unveiled as the housewife of the future."

Some of the stories would be interesting no matter how they were told, though. Take for example Jr. and His Soulettes, a preteen R&B band from Oklahoma City that consisted of a brother and three sisters; the entire pressing of their lone album, Psychodelic Sounds, was destroyed when their father (also their songwriter) shrink-wrapped them in the butcher shop where his brother worked, because the high-heat machine he used warped every record. (Most of the band's surviving music comes from four subsequent singles.) The Rhodes Kids, one of countless family bands in the early 70s (a la the Cowsills and the Partridge Family), got involved with notorious pornographer and mob figure Michael Thevis, aka "the Sultan of Smut" and "the Scarface of Porn," who released several of their albums on his GRC label before being jailed in 1974 for conspiracy to commit arson and distribution of obscene materials. (He escaped in 1978 and murdered the informant whose testimony led to his indictment.) Another family band, Captain Hook and His Pirate Crew, were led by Von R. Saum, who'd lost a hand and a leg in a motorcycle crash while he was a member of a biker gang in his teens; he "awoke in the hospital to the call of Christ," and after getting married and starting a family he launched his act, which included a ventriloquist, comedy sketches, and Christian pirate songs.

The biggest problem with the book is that it rarely adequately describes the music—though given how odd much of it is, that's an admittedly difficult task. This makes the companion two-CD set, sold separately by Now-Again, especially valuable. Instrumental funk tunes by the Invaders and Cleo McNett (whose cut here, "Snap," was sampled by DJ Shadow on "Soup") would still sound good put up against mainstream releases from the era, but most of the 24 tracks are off-center in one way or another. There are a lot of bad singers on these discs, and many of them use an unctuous, lounge-worthy croon, whether they're attempting country, rock, funk, or easy listening—the vocals enforce a sort of sameness on the music, turning it into wallpaper. Most of the songs sound like earnest bids for commercial success by artists ranging from mediocre to talent free, and though their chutzpah and obvious belief in themselves are charming, that's not enough to make me want to listen to any more cheesy lounge singers.

Some of the music, though, is genuinely warped, made by artists who clearly exist in their own worlds. Gary Schneider gives the vocoder-­driven love song "Cast Your Fate to the Wind" a chintzy electro vibe using what sounds like one of those Baldwin organs they used to always sell in shopping malls. On "Monkey Bridge" the husband-and-wife team of Jonema Wintergate and Kalassu Kay, aka 33 1/3, load up their quasi-tribal funk with truly horrible singing, weird guitar effects, synth stabs, interjections of noise, and animal calls. "Elton John Medley" by Silk & Silver is sublimely bad, but the weird magnetism in the overwrought singing of pianist Robert Baldwin makes it sound like a precursor to the glammy warble of the Frogs' Jimmy Flemion.

The Internet is almost entirely responsible for turning private pressings from the sole province of obsessed collectors to a subject worthy of a widely distributed book; many of these albums were shared online during the heyday of MP3 blogs. The Internet has also helped drive private-press releases to the brink of extinction by making it easy for anyone with access to a computer to get their music out there via YouTube, Soundcloud, Bandcamp, CD Baby, and similar platforms. But though DIY online distribution has largely replaced private pressings in the musical ecosystem, that doesn't necessarily mean that the two habitats support the same kinds of weirdos.

It's true that there are parallels. In both cases, it costs money to make and share recorded music, which tends to weed out the less committed (though admittedly the process is much cheaper today). Accessible digital home-studio equipment makes it possible for today's fringe musicians, like their predecessors in the world of private pressings, to produce and distribute their work entirely isolated from industry professionals who might provide quality control or normalizing influence. And both types of artist seem equally likely to labor in the additional isolation of obscurity, since to find somebody on Bandcamp (for instance) you usually have to look for them.

But there's one big difference: If you use the Internet to post and distribute your material, it's much harder to avoid becoming aware of how the rest of the musical world operates. It's harder not to know you're a weirdo, in other words. Some of the private-press artists featured in Enjoy the Experience really seem to be working in a vacuum—a vacuum that's been punctured by the Internet in the years since—and thus have no idea how strange they sound. That baffling, endearing lack of self-­consciousness is the most inspiring thing about off-the-wall private-press releases—and it's often much easier to take to heart than the music.

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