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Hugh Ryan’s Book Notes music book for his book My Bad

“Receiving a mixtape was the highest honor; making one, the greatest responsibility.”

In the Book Notes series, authors create and discuss a music playlist that relates in some way to their recently published book.

Previous contributors include Jesmyn Ward, Lauren Groff, Bret Easton Ellis, Celeste Ng, T.C. Boyle, Dana Spiotta, Amy Bloom, Aimee Bender, Roxane Gay, and many others.

Hugh Ryan’s My Bad melds personal experience with history to form a book as inspiring as it is informative about queer life in the modern era.

Kirkus wrote of the book:

“Bracing…A clear-eyed reckoning with a decade that promised freedom and delivered transformation, unevenly and at a price.”

In his own words, here is Hugh Ryan’s Book Notes music playlist for his book My Bad:

I got my first Walkman in the fall of 1992, right as I started my freshman year of high school. It was safety yellow and indestructible, and though at the time it seemed like magic, I now realize it added a backing track of hiss and grain and warp to every song it played. It was my most precious possession: a portable bubble between me and the world.

I only had a handful of cassettes, the most important of which was a mixtape my older brother left behind when he went off to college, which introduced me to Arrested Development, the Indigo Girls, Pink Floyd, and (unfortunately, obsessively, for a short while) Rush. The internet barely existed, and the closest thing to streaming music was the scream the modem made when you went online (in retrospect, that should have been a warning). If you wanted to find new music, you had three options: spinning the FM dial and hoping to find a cool new station (this was before the Telecom Act of 1996 killed local radio), standing in the listening booths at Tower Records, or getting a mixtape from a friend.

Receiving a mixtape was the highest honor; making one, the greatest responsibility. When I started writing my new memoir in essays, My Bad: A Personal History of the Queer Nineties and Beyond, I imagined it as a mix from me to my readers – in fact, one of my early working titles was “Mixtape.”

As a historian, I use music to get at memories we can’t access in other ways. I’ll ask the person I’m interviewing what music was playing in the moment they’re describing, or I’ll put on an artist they loved and ask who they were when that song meant everything to them. I did the same with myself while writing My Bad, so the book is studded with music – mostly the ambient hits that were inescapable at the time. If you were alive in 1995, The Bayside Boys remix of The Macarena is now physically encoded in your DNA, and you may be liable for compensation from Los del Río.

Listen: I would never have put The Macarena on a mix. That would have been a violation of the sacred bond between mix-maker and mix-listener. The mixtape revealed your soul; put on a top pop hit and you branded yourself a sellout, the worst thing you could be in the Nineties (well, aside from a fag, but that ship had already sailed for me).

I couldn’t have known at the time that the mixtape, like so many other things, was about to disappear. In 2001, Apple released the first iPod; in 2002, I won a cheap knockoff MP3 player by being the 100th caller on the Z100 Morning Show, and I never made a mixtape again. And let’s be real: streaming is nice, but clicking “add to playlist” in no way compares with the adrenaline rush of slamming the “record” button when you heard the first notes of a new favorite song, catching the last words the DJ said over the intro, permanently transforming the phrase “and this is for Diana in Lackawana!” into a private joke with your friends.

RIP: The Mixtape, 1992-2002. I miss you; or I miss the you I was when you were around. It was a micro-generation, part Gen-X, part Millennial. I guess they call us Xennials now. As with everything else, we grew up with one way of doing things, and right as we hit adulthood, the internet “disrupted” (or perhaps “ruined”) that way of life. The loss of mixtapes is just one among a million tiny cuts that have permanently separated us from the way we lived in the 20th century. That’s the heart of My Bad: a reckoning with how life changed in and around the millennium. The 1990s were a hinge decade, which started analog and ended digital. We lost and gained so much, I had to write a book about it.

So: this is my requiem for the mix, a personal, 11 track playlist, one song for each of my former musical selves, my mixtape years – the same years that make up the majority of My Bad: A Personal History of the Queer Nineties and Beyond.

1992: Closer to Fine, The Indigo Girls

Thanks to my brother’s mixtape, The Indigo Girls were my first musical obsession – so much so that I became a minor hub on the Indigo Girls bootleg trading circuit, a loose network of lesbians, not-yet-lesbians, and guys-who-wished-they-were-lesbians, which I found via early internet Bulletin Board Systems. Their 1990 album “Nomads, Indians, and Saints” had a tiny pink triangle on a teal background; it was the first time I encountered the secret language of queer people that guided me through the rest of the decade. But the soaring, soul-searching “Closer to Fine” was the song that capped off every party, every road trip, and for a while, every mixtape I made.

1993: Crucify, Tori Amos

Trish was a year younger than me, a clove-smoking proto-goth who was as unpopular with her classmates as I was with mine. We bonded in biology lab, where we were partnered to dissect frogs and sheep uteruses under the watchful eye of our creepy bio teacher, who harangued us about how lesbians would one day take over the world because they did not need men. Budding misandrists that we were, this sounded like a pretty sweet deal. Trish introduced me to Tori Amos on the first mix she made me. We’d get home from school, put on Little Earthquakes (Tori Amos’s masterpiece of synth and fury), and immediately call each other so we could listen to it at the same time.

1994: Send Me On My Way, Rusted Root

I was a weird gendered kid in a cloistered suburb; I wasn’t clear on what it meant to be gay or trans or queer. But I was obsessed with long-haired, androgynous men. There were 42 of them in the band Rusted Root, give or take, and I wanted them to play me like a pan flute. This was my first experience of musicians as style icons, so I grew my hair out, got a bracelet with Kokopele woven on it, and cut all my jeans into bell bottoms – neo-hippie flair as a way of queering gender. Still to this day, Rusted Root is the band I have seen in concert the most, and “Send Me on My Way” sets me spinning, arms out wide, like the stoners at the back of every jam band concert.

1995: Be My Lover, La Bouche

WKTU – Keep it Turned Up! – was our local dance station, and my limbic system was permanently tuned to it in 1995. I channeled all the energy and emotions of puberty into midnight solo dance parties to Eurotrash techno. No one – no one – appreciated it when I put them in the middle of a mix tape (where the highest energy songs should go, I felt). The late 90s and early 2000s were the best years for queer clubbing: far enough post-Stonewall that there was less danger in going out, but not yet so acceptable that the bars and clubs were flooded with straight people. Although underappreciated on a mix tape, everyone loved La Bouche on the dance floor.

1996: Untouchable Face, Ani Difranco

Jennifer was the coolest girl in town. She sat at the back of the bus in elementary school and told dirty jokes with the boys; in high school, she was the first person to rock vintage t-shirts and ironically enjoy disco. Our school had a tradition called senior sleep out, where the entire senior class partied in the woods all night and rolled into class the next day looking absolutely gross. I didn’t drink and Jennifer could outdrink anyone, so at 5am, we found ourselves the only (sort-of) sober stragglers tending the bonfire, and we bonded over knowing every word to We Didn’t Start the Fire. The next day, she introduced me to the cool CD store, the one on Central Avenue that you needed a car to get to, which sold rarities, foreign imports, and bootlegs. We both bought copies of Dilate, the new album by Ani DiFranco, and “Untouchable Face” became the song I put on the mixtape for every person I secretly had a crush on (which was pretty much everyone I ever made a mixtape for). Tori’s slow, angry longing – her desire and her anger over that desire – felt far too relatable.

1997: Strange Fruit, Billie Holiday

I assume I heard jazz before I got to college – as hold music, or perhaps when my parents listened to NPR. But the genre didn’t really penetrate my tastes until the second semester of my freshman year, when an older dyke took me under her wing and made me a wacked out mixtape of cult music I should already know, everything from Patti Smith to Skinny Puppy to Billie Holiday. “Strange Fruit” was a gateway drug to Bessie Smith, Ella Fitzgerald, Django Rheinhardt, Duke Ellington, and the entire world of jazz standards. I don’t think I ever felt this cool again (don’t worry though, I was not actually cool: my other musical obsession in this moment were 3rd wave pop ska bands like Dance Hall Crashers and Reel Big Fish). Now the algorithm suggests new music for me, and though it’s often right, it’s much less exciting.

1998: Street Spirit (Fade Out), Radiohead

In the summer of 1998, I backpacked around Europe with two younger, wealthier friends, because I had somehow convinced their parents that I was an appropriate chaperone for a pair of sixteen-year-old identical twins. Nothing went right and it was perfect. At some point, I lost my 10 CD holder, and was forced to listen to their music, which was a lot of classic rock (they were both guitarists) and Radiohead. Previously, I thought Radiohead was for pretentious try-hards. But listening to Thom Yorke’s plaintive wailing as our train tracked the Danube River from Vienna to Budapest, I realized I was a pretentious try-hard, and Radiohead was amazing.  

1999: Glory Box, Portishead

I met my first serious boyfriend in 1999, and although this is inexplicable to me now, “Glory Box” by Portishead was my fuck music – along with a wealth of other (mostly British) trip-hop bands like Massive Attack, Tricky, DJ Shadow, and Morcheeba. If this appeared on a mixtape I made, I was trying to get some. If you read My Bad, put on the Portishead album “Dummy” when you get to the essay “Never Let School Get in the Way of Your Education.”

2000: Shirley, L7

Around the end of college, I went from fetishizing androgynous hippies to fetishizing androgynous punks. “Homocore” was a genre I discovered via Riot Grrrl zines and Take Back the Night rallies. Furiously feminist, we slammed our bodies together to L7, Tribe 8, Skunk Anansie, and Pansy Division. Within a year, my long hair was replaced by bleached spikes, and my dangly hippie necklaces with a spiked velvet dog collar.

2001: Get Ur Freak On, Missy “Misdemeanor” Elliott

“Hot Boyz” and “The Rain” were already on my radar, but Missy Elliott’s third album, Miss E…So Addictive was, as its title claimed, absolutely addictive. No skips. Many a bad party was saved by simply letting it play through on repeat. It became a litmus test for the bars: how did the DJ react when we requested Missy? The music throbbed with energy and sex and everything you wanted from a night out. If the DJ refused to play “Get UR Freak On,” they were probably racist.

2002: Book of Love, The Magnetic Fields

After September 11th, my musical tastes took a turn for the mopey. I don’t know if those two things are related, but when I look back, the turn is unmistakable. The Magnetic Fields triple album, 69 Love Songs, was my first dive into the world of acoustic, sad, twee, monotonemumbleboy singers who would rule my world for the next few years. Still to this day, if I want to have a good cry first thing in the morning, I pop on The Magnetic Fields or Elliott Smith.


For book & music links, themed playlists, a wrap-up of Largehearted Boy feature posts, and more, check out Largehearted Boy’s weekly newsletter.


Hugh Ryan is the award-winning author of When Brooklyn Was Queer (2019) and The Women’s House of Detention (2022). He teaches creative nonfiction in the MFA program at the Bennington Writing Seminars and runs the Queer History 101 Book Club with world-famous performer Peppermint. He lives in Brooklyn.


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