How We Listened to Music Over the Last 25 Years

HitClips are often described as toys, but to 7-year-old me, they were legitimate listening devices—perhaps even the only listening devices that had cultural cache. My friends and I were not discussing the intricacies of sound quality, we simply wanted the endorphin rush of putting on glitter bell bottoms and ​​Lip Rageous *NSYNC Lip Balm and singing, “If you want it here’s my heaaaaart… no strings attached” over and over. –Vrinda Jagota

Radio Shack Computer Speakers

Ever since my freshman year of college, in 1999, I have owned two ugly, gray, decidedly non-audiophile RadioShack computer speakers. I still remember blasting newly acquired MP3s, via Winamp software, again and again over those dumb speakers in my dorm room. In hindsight, I wonder if their limitations pushed me into the more singer-songwriter music that I increasingly leaned toward during those awkward couple of years—Ben Folds, Guster, Elliott Smith, the acoustic version of Wilco’s “I’m Always in Love,” along with a turn-of-the-millennium melange of live bootlegs by your Matthewses and Mayers—music that could come across without a subwoofer (or any bass, for that matter).

Over the two decades-plus since, I’ve acquired plenty of better listening gear (and wider listening habits), but there was a comforting familiarity to the RadioShack set; in younger years, I often used to fall asleep listening to them. Plus: They just wouldn’t break! Finally, when my older child was doing school from home during the pandemic, I reasoned that I could probably sub in a huge tech company’s fancy new speaker for my own setup, and let the kid use the RadioShacks. Well, shocker: The fancy new model was totally useless, and now that the kid is back in school, I am totally stealing those drab little speakers back. –Marc Hogan

Pink iPod Mini

I wanted it immediately: the original iPod mini, in pink, of course. It was 2004, and I convinced my parents to buy one for me because my commute to middle school was 45 minutes each way, and there were only so many CDs I could carry around with my knockoff Discman. My friends were impressed, but I was obsessed: The Mini was dense like a brick and sheeny like a candy bar wrapper, and with its four gigabytes of hard drive space, I felt like I had my own radio station. I loaded up Beyoncé and Modest Mouse and the Killers. I collected iTunes Store vouchers from strawberry-scented lip balms and bought digital downloads of Gwen Stefani’s Love. Angel. Music. Baby. the day it came out. The Mini came with me everywhere, on car trips and bus rides, even to the Christian summer camp that banned secular music. After hours and hours of listening, I started to hear things in my favorite songs that I hadn’t before: the carefully placed upstrokes in the main riff of Green Day’s “American Idiot,” the way the backbeat scaffolds “Wonderwall.” My guitar teacher at the time was trying to get me into Jeff Buckley—guess I wasn’t listening. –Anna Gaca

Griffin iTrip FM Transmitter

In 2005, I started pulling into my high school parking lot in Ona, West Virginia in a hand-me-down Toyota Corolla with manual locks and crank windows. It had an AM/FM radio but no CD player, no tape deck, and certainly no AUX port. With all due respect to the area’s local radio stations of the era, I was an iPod-carrying Pitchfork reader and I wanted to listen to the good stuff. Imagine a proto-Baby Driver—except with no interest in heists and zero getaway driving skills.