Playlist: It Was The Summer of ’99

All the songs on this playlist came out between 1996 and 1999, but the majority came out in ’98 and ’99. Two of these songs came out in the fall of 1999, not the summer of 1999, but that’s okay, because now it’s the future and time is fluid? Because they’re on the same mixtapes as the summer songs, for me.


My last week of boarding school in Northern Michigan was consistently sunny and temperate in the way seven consecutive days rarely are anymore. It was warm enough to sneak off-campus to the State Park, where we could smoke cigarettes and eat congealed Nachos out of styrofoam containers and hold hands desperately for no reason, scared to leave each other for our third-choice colleges or conservatories and scared to talk about how scared we were. It was warm enough to make out in the woods and for my favorite writing teacher to take us across the lake on his boat, and for my boyfriend and I to have an epic fight on the dock that ended with him throwing my favorite water bottle into the deep beyond, an action for which he will never be forgiven.

I’d always loved leaving because I never liked anywhere I’d ever been, but I didn’t want to leave that place. Still, I didn’t cry at graduation even though everybody else did, but after sleeping through the whole five-hour drive home to Ann Arbor I cried the whole night, unwilling to unpack literally or metaphorically. I was in the class of 1999. So then it was the summer of 1999.

The Daily Beast wrote that the summer of 1999 was “our last innocent, giddy summer.” The economy was booming, Clinton had survived impeachment, everybody was collecting Beanie Babies, Britney Spears had recently unleashed her iconic bubble gum pop and sweet schoolgirl smile upon us all and Destiny’s Child was just getting started.

“May to September was a time to take nothing seriously,” writes Nathan Webster in The Daily Beast, “to simply enjoy summer days that were vapid and ridiculous, innovative and exciting. Like the long-dead refugees from the Roaring ‘20s, we didn’t know it may never be that good again.”

It’s funny, that idea, ’cause I wrote in my diary at 3:41 AM on June 6th, 1999, with the precise authority of a 17-year-old, that “the world is going downhill” and that “I think we were okay in like, 1997, and then all of these kids started to shoot each other.” I was talking about Columbine, which happened in April 1999. I continued, inexplicably: “But the world is good now because we have low-fat cheese and computers that don’t weigh very much and we can find out anything on the Internet. There are some wonderful magazines and books.”

I think my summer of 1999 was actually about what Webster says it wasn’t; fear that “it” (what? I didn’t know.) would never be that good again. It was about tentative hope for a future where I could indulge my hungers, literally and also for experience, which Drew told me was “the bread of a writer.” This was the summer I decided I needed six-pack abs, and also that I wanted to be a writer.

I worked at GapKids and wore Victoria’s Secret camisoles with built-in bras and hung out with my friends Jake and Zach, who’d gotten into their first-choice colleges. They played in bands and read Borges. We climbed the roofs of elementary schools, saw indie films downtown, drank milkshakes at Tio’s, and they tried to get me to understand how “listening to music” could be a stand-alone activity. Jake made me lots of indie-pop mix-tapes. I felt smart when I listed to them on my walkman, smarter than when I ran around the neighborhood listening to Britney Spears and “The Rockefeller Skank.”

Taste was important, and I wasn’t sure if mine was refined enough. I felt free when Zach told me he thought I had my finger on the pulse of our generation and that I should read Douglas Coupland, who Zach said had his finger in that same spot. I could become famous and successful like him without having to read Borges, I guess. Coupland is responsible for popularizing the term “Generation X.” He writes about “mass culture” and is a “satirist of commercialism.” Jake lent me Life After God, and I never gave it back. Coupland definitely wouldn’t have agreed that 1999 was an innocent summer, only that in 1999 we were able to pretend like it was an innocent summer.

I really saw myself in two pieces, then — like one side was an artist who wrote about death and bodies of water and took abstract Polaroids and listened to The Magnetic Fields and read Raymond Carver and the other side was an idiot who read Bridget Jones’ Diary and shopped at Abercrombie and took notes from fitness magazines and listened to Britney Spears. (This was 1999, remember, so it was okay to be this torn up about your authenticity as an artist, and whether or not your job was “soul-sucking.” By the time we graduated college I would’ve done anything for a job, any job at all, my soul was up for grabs! It seems so indulgent now.) That’s why it mattered so much when Zach recommended Douglas Coupland, because Coupland’s book covers were sometimes the same color pink as Britney Spears’s pillow-bed on the cover of Rolling Stone.

I think Jake’s parents subscribed to Rolling Stone — I’m not sure, just that somehow that legendary April 1999 issue was on their side table, the one where a 17-year-old Britney Jean lay atop hot pink satin sheets, clad in only polka-dot hipsters, a glossy black bra and a suggestively splayed cardigan. She’s on the phone and also clutching a purple Telletubbie (!!!!). People were very disturbed about Britney Spears and whether or not she’d had breast implants. The American Family Association said the cover was “a disturbing mix of childhood innocence and adult sexuality,” which felt right. I mean: weren’t we all?

Riese is a Jewish lesbian and the 37-year-old CEO, CFO and Editor-in-Chief of Autostraddle.com as well as an award-winning writer, blogger, fictionist, copywriter, video-maker, low-key power lesbian and aspiring cyber-performance artist who grew up in Michigan, lost her mind in New York and then headed West. Her work has appeared in nine books including "The Bigger the Better The Tighter The Sweater: 21 Funny Women on Beauty, Body Image & Other Hazards Of Being Female," magazines including Marie Claire and Curve, and all over the web including Nylon, Queerty, Nerve, Bitch, Emily Books and Jezebel. She had a very popular personal blog once upon a time, and then she recapped The L Word, and then she had the idea to make this place, and now here we all are! In 2016, she was nominated for a GLAAD Award for Outstanding Digital Journalism. Follow her on twitter and instagram.

Riese has written 2607 articles for us.

29 Comments

  1. Oh the late 90s/early 00s, when the greatest social activism I could conceive of was cutting the labels off my branded clothing and unironically wearing a Radiohead concert tee to a Naomi Klein No Logo book tour.

  2. Britney Spears, the self professed virgin with hits like, „Hit Me Baby One More Time“.

    Class of 99, and weirdly enough I still tell all my friends to always wear sunscreen.
    Happy summer! And thanks for this playlist!

  3. “size of our love” by sleater kinney (and the whole Hot Rock album actually) really does feel very 1999 to me… it was startling to hear at first (it sounded so different) but after a few listens I was like, oh, this one of their best albums?

  4. I thought I was getting a playlist, I had no idea I was in for an essay that would clutch to my soul. WOW.

    This was absolutely breathtaking and beautiful. Thank you.

    (Summer of ‘99, I had just turned 13. I spent my first summer at sleep away camp and list all my “baby fat” — don’t worry, I’d gain it back — and kissed my first boy. That Britney Spears cover was everything to me. As they say, what a time to be alive!)

  5. I remember reading Life After God in the break room at work and my very religious elder coworker asking me about it 😐

    I thought I wasn’t going to connect with this playlist bc my tastes went very goth/industrial in ’99 but THERE ARE A FEW JAMS ON THERE

    • YES I TRIED TO KEEP IT ECLECTIC YOU KNOWWW??

      i also read Life After God in the break room at work, eating my little pre-packaged snacks in the GapKids stockroom. i felt like consistently loathed by everybody who worked there, and my books DID! NOT! HELP! the book that got the most negative feedback from coworkers though was Fear & Loathing in Las Vegas, somehow.

  6. The summer of ’99…I had no idea I was about to meet my future wife, have my life flip head over heels…only to have it flip again, 18 years later, a millennial’s lifetime later. And learn to un-wife and re-life in another summer that will indelibly mark a turning point once more.

  7. I remember asking my mom for the cassette tape of … Baby One More Time. So many hours spent singing into my hairbrush, good times!

    I remember asking my mom if I could tie my shirt like Britney for school. I was 9/10. She said no. Oddly enough she let me tie my shirt when I was 12, on a trip to the grocery store. I felt really exposed and uncomfortable. Never did it again.

  8. We are of the same vintage. I really appreciate this. The start of school shootings really changed things for high schoolers just slightly younger than us, I think, and unfortunately continues to influence the high school experience.

    After my very sheltered and quiet midwestern high school life I spent time in NYC. Some of my very, very favorite things from that era were still swinging… reclaim the streets parties and critical mass bike rides. So liberating and so much fun.

    • yes! i ended up going to college outside of NYC in the fall of 99, and then dropped out and moved to manhattan in 2000, for about seven months. then came back to the midwest for a more budget-friendly college experience. it was a very different time!

      i was showing a much younger friend the gun episode of My So-Called Life recently and was just… the whole episode is that there is a gun in somebody’s locker. nobody is shot or killed. and everybody is terrified and traumatized by it and my younger friend was like “why is everybody acting like this?” the episode just didn’t make sense at all to them, didn’t compute. because to them, you know, a gun in somebody’s locker is not that scary, now that we’ve lived through so many times that gun was actually in somebody’s hand.

  9. I haven’t even listened to the playlist yet but I just love this essay so much. (Let’s be real, I love everything Riese writes.)

    I was class of ’98, so the summer of 1999 was the summer after my freshman year of college. During that freshman year I’d managed to out myself to my entire class and date/break up with my first and second girlfriends! Whee! I also spent every Thursday (and sometimes Tuesday) night for a full semester at a gay dance club called Pegasus. Approximately 80% of my energy and brainspace was occupied with trying to figure out how to be the token gay girl in the musical theater program. It was a JOURNEY.

    That summer I got a job as a “canvasser” for an environmental group called Clean Water Action, which meant riding around in a van with a bunch of new-age hippies & knocking on doors to ask people for donations. I’m not sure why I wanted to do this, because I hate talking to strangers and am a terrible salesperson, but in retrospect I think it was out of a desire to NOT see anyone from high school. I was out at college (even though it was not completely by my own choice) but not out to my family and was also not ready to come out to anyone I’d known in my “former life” as a straight person. With new people I could just be queer from the beginning. It felt easier. Some of my co-workers were also queer, including a super cool girl with a shaved head who was really into Ani DiFranco (of course). On the surface the group seemed like an odd mix of people but we were all outsiders in our own way and it was kind of perfect.

    ANYWAY. Thank you for the nostalgia. I’m gonna go listen to the playlist now.

  10. My phone does this thing now where it suggests the next thing I might want to google based on the page I’m currently on, and when I just went to open a new page from this one it suggested ‘Britney Spears videography,” which is all to say good job Riese ?

  11. My brain:

    Disturbing mix of childhood innocence and adult sexuality = Corey Mason a high schooler, Empire Records trying to seduce a grown adult in mix-matched lingerie

    It’s disturbing to adults because we don’t want her to get hurt, even people having moral panic about teen sexuality at their core it’s the same thing just with an unhelpful response.

    …I think the older I get the madder I will be about the adults in positions of power that did me and other kids harm because it wasn’t even out of a misguided attempt to protect us.

    90’s nostalgia makes me thinky ok.

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