The Lost Art of Mixtapes
There was a time when telling someone I made you a playlist required considerably more commitment.
You couldn't search for ten songs, drag them into order, hit Share, and send the whole thing across the country in four seconds. You needed equipment. You needed blank tapes. You needed patience. And depending on how seriously you took it, you might need an entire afternoon.
I still remember my yellow Sony Walkman and the shoebox full of mixtapes I made for myself — tapes for certain moods, certain songs I couldn't stop playing, certain moments I apparently believed deserved their own soundtrack. The handwriting on the little cardboard inserts changed. The songs changed. The technology eventually changed.
But I loved those tapes.
Maybe that's part of why a mixtape found its way into I'm With The (Boy) Band.
In the book, Jaxsper Finn's best friend Marsha sends him off to California with one. He's leaving Kansas for a Malibu mansion, a reality television show, and — most importantly, as far as Jaxsper is concerned — the chance to live with his favorite band, Three North. Marsha labels her creation Absolutely Essential Emergency Songs.
Which feels about right. Because a good mixtape wasn't really a collection of songs. It was an emergency kit.
Before Playlists Did All the Work
Making a mixtape around the year 2000 involved choices. Actual choices.
A cassette could only hold so much music, which meant every song occupied valuable real estate. Put too many long songs on Side A and the final track vanished halfway through the chorus. Leave too much space and you'd spend ninety seconds listening to the faint hiss of blank tape before the side clicked to a stop.
So you strategized. You decided which song opened the tape — that mattered. You decided what ended Side A — that mattered more. Then came Side B, which was essentially a sequel, and therefore carried enormous expectations.
If you were recording from CDs, there was a small choreography to it: cassette deck armed, CD cued to the right track, fingers poised over the buttons.
Press record. Press play. Hope.
Recording from the radio raised the stakes even higher. You waited for the song. And waited. Then the DJ finally played it and you lunged for the stereo like someone had announced a national emergency. Sometimes you caught the beginning. Sometimes you got thirty seconds of a radio personality talking over the intro — which meant you'd spend the rest of your life knowing exactly when that voice was about to trample the opening guitar riff.
These were the risks we took.
A Mixtape Was Also a Message
The part I miss most isn't the cassette. It's the intention behind it.
When someone made you a mixtape, they had spent time thinking about you. Not theoretically. Literally. They had stood somewhere — a bedroom, a dorm room, beside a stereo in the living room — and thought: this song. They need this one.
Maybe the lyrics said something the person couldn't. Maybe the song brought back a road trip, or a concert, or a ridiculous night neither of you would ever properly explain to anyone else. Maybe it was there because you once said you liked it, and they remembered.
That might have been the best part. The remembering.
Marsha's tape works that way. Her choices aren't meant to be the definitive list of the greatest songs ever recorded — that's not what real mixtapes were anyway. Real mixtapes were messy. A song from the 1980s might sit beside something six months old. A huge pop single could be followed by an alternative track your friend insisted nobody else appreciated properly. Something serious might land right before something ridiculous. The only genre holding it together was the person making the tape.
On Jaxsper's, Marsha puts “Video Killed the Radio Star” next to “I'll Stand by You.” Britney Spears shares space with Fiona Apple and Tom Petty. There are songs by Three North, because of course there are — Jaxsper is heading to Malibu to live with them.
Then she adds instructions:
If you miss me: Track 2.
If you're nervous: Track 3.
If you need your moody, artsy, edgy-star moment: Track 9.
And when you miss home? Play everything.
Not literally — as Marsha points out, that would probably break the Walkman. But emotionally? Absolutely.
The Little Plastic Time Machine
Here's something I love about cassettes now that I didn't understand when I was carrying them around: they remember things by accident.
A playlist today can change forever. Songs disappear, songs get added, you reorder, you swap out whatever you're tired of. A cassette stays stubbornly itself. That weird song you loved for three weeks is still there. So is the one you associate with a person you haven't spoken to in twenty years. So is the terrible recording where you missed the opening five seconds. The handwriting on the case stays exactly as you wrote it, and the title you thought was clever stays exactly as clever — or as not-clever — as it was.
You don't just hear the music again. You meet the version of yourself who chose it.
That's why I like imagining Jaxsper years later, finding Marsha's tape in a box somewhere. Maybe the handwriting has faded. Maybe the case is cracked. Maybe he no longer owns anything that can play it. But he'd still know what Track 2 meant. He'd still remember why Track 4 mattered. He'd know exactly what Marsha meant when she wrote Your sparkle is permanent.
And suddenly the tape isn't about music at all. It's about being seventeen and terrified and excited and leaving home. It's about the friend who knew you before anybody else did. It's about somebody saying, in the language available to teenagers everywhere: wherever you're going, take me with you.
Before Everything Became Instant
One reason I've loved returning to the year 2000 while writing this series is that it sits in such an interesting place. The world was already becoming more connected — but not everything was instant yet. You could go somewhere without everyone knowing where you were. A photograph could exist without immediately becoming public. A message could wait. A song could take effort to find. And telling someone this reminds me of you sometimes required a blank cassette, a stereo, a pen, and ninety minutes of your life.
Was streaming easier? Obviously. Would I give it up? Not a chance.
But every so often I think about that yellow Walkman, and the shoebox, and all those tapes filled with versions of myself I didn't realize I was preserving.
And I miss pressing play.
What About You?
I don't want to be out here all alone. I'd like to hear from you. Did somebody make you a tape you still remember? Did you make one you'd be a little embarrassed to hear now? Maybe there's a Track 2 of your own — the song that still means something years later.
I'd love to hear about it. Leave a comment and tell me what was on yours. (Bonus points if you remember losing the first five seconds to a DJ.)
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