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Rock and Roll Book Club: 'Tori Amos Bootleg Webring' celebrates the early days of music fandom on the internet

In 'Tori Amos Bootleg Webring,' Megan Milks looks back on the days of online music fandom before Google, before Napster, and before YouTube.
In 'Tori Amos Bootleg Webring,' Megan Milks looks back on the days of online music fandom before Google, before Napster, and before YouTube.Jay Gabler/MPR

by Jay Gabler

September 30, 2021

Do you remember the first thing you did when you got online? For gen-Z, that may have been connecting with friends or watching videos, but when Megan Milks logged on in the mid-1990s those weren't options. "My friends weren't online yet," they write, "although whenever one of them got connected, I sent out thrilled emails that were met with unimpressed responses: 'I am trying to call you.'"

File sharing? When Milks's fellow Tori Amos fans wanted to download pictures of their heroine, let alone sound files, they'd have to start the download process and let it run all night. If you wanted to trade concert bootlegs, you were going to need a dual cassette deck (later a CD burner), and you were going to need a webring. Hence the title of Milks's charming, poignant new book, Tori Amos Bootleg Webring.

It's part of an Instar Books series called Remember the Internet, celebrating past eras in online culture. (The first volume, Tumblr Porn, examined the risks of content crackdowns like the one currently happening at OnlyFans.) Milks focuses on the second half of the 1990s, when the author was a teenager and Tori Amos was in the early years of her lifelong musical odyssey.

Every show was different, so if you were a fan, you wanted to hear every one. Websites representing the next generation of fan culture that previously thrived on zines and newsletters were sprouting up, but without a reliable way of searching for fansites, a peer-curated culture relied on tools like webrings: links among trusted sites, helping fans find more like the one they were on.

As Milks points out, gaining admittance to the top tier of Tori Amos bootleg webrings was no mean feat. The Tori Traders Ring required members to maintain a library of at least ten bootlegs, to use high bias type II cassettes (you could build your library by trading two blanks for a full), to provide two references "who would vouch for your integrity as a trader," and "lastly, you had to complete four trades with ring members who were not references, one of whom had to be a ring leader."

What did Tori Amos make of all this? She was aware, it seems, and like many artists she understood that while bootlegging had to be legally forsworn, but also got that these bootleggers were her biggest fans: swapping of commercially released material was frowned upon, and Amos's team had enough other things to worry about that years of high-quality DAT soundboard recordings of her shows were neglected to ultimately deteriorate beyond repair. "We literally could have had every show from '96 and '98," moans one leading bootlegger. "What a loss. What a mega loss."

Tori trading rings were never just about the music, though: they were about the community. Milks bonded over Tori Amos with a younger teen named Chris; the two developed an intense friendship that Milks now regards as "a queer intimacy. It was meaningful, and it was confusing." Chris later came out as gay; Milks is queer and trans, and as a teenager was struggling with their relationship to their own body. The internet was at once freeing and challenging: they could escape into a text-based online persona, but ultimately they were still living in their own body and had to come to terms with it.

Ultimately, Milks went off to college and Napster launched, effectively ending an era. Today, fansites for Tori Amos and innumerable other artists have online libraries of downloadable bootlegs, while artists like Bruce Springsteen are putting increasing numbers of professional show recordings up for sale. The book opens with a painful scene but inevitable scene: Milks is donating their heavy cases of carefully labeled bootleg cassettes to Goodwill.

I could recreate the collection now if I wanted to. My bootleg trading page is still, improbably, online. Hosted on Tripod, it may never go away. The bootlegs themselves I can find as digital files housed on fan sites like But downloading a digital archive is hardly the same as building an analog collection, where each tape is associated with a person and an exchange. The taping itself required time and care: you'd generally listen to the whole tape front to back each time you duplicated it (no high speed dubbing! a hard rule), a ritual that for me also involved copying out the setlist by hand, maybe alternating the colors of my pen ink, adding tiny fairy doodles or stickers, and addressing the mailing envelope in neat letters. You knew you would get something special back, a new tape to add to your trading list.

While Tori Amos Bootleg Webring isn't really about Tori Amos, it must be acknowledged that her status as an object of early online adoration is notable. As Milks observes, Tori Amos was only the second woman musician to be certified as a topic on Usenet. She achieved that status in 1994. The first, certified all the way back in 1985? Kate Bush. "There's something about each of them," a fellow "early online Toriphile," tells Milks, "that attracts geeks, apparently."

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Upcoming Rock and Roll Book Club picks

Tune in to The Current at 8:30 a.m. (Central) every Thursday morning to hear Jay Gabler and Jill Riley talk about a new book. Also, find Jay's reviews online.

October 7: The Storyteller by Dave Grohl

October 14: Who Got the Camera? A History of Rap and Reality by Eric Harvey

October 21: Where the Devil Don't Stay: Traveling the South with the Drive-By Truckers by Stephen Deusner

October 28: I Put a Spell on You: The Bizarre Life of Screamin' Jay Hawkins by Steve Bergsman