The Rolling Stone 500

In the first week of 2021, my friend Andy (a longtime writer and music nerd) asked me to join him on a year-long music challenge: listen to and review each of Rolling Stone’s 500 Greatest Albums of All Time. Ten albums and ten reviews a week, for fifty weeks.

It was a crazy idea, but it appealed to me in ways that went far beyond music:

• It would force me to engage with my media choices—less passive consumption, more active consideration.
• It would expand my palate across genres and time periods. It’s never been easier to access the best of everything; why limit ourselves to what’s right in front of us?
• It would shift my listening away from commercially curated playlists and towards whole-album artistic expression—trusting artists and tastemakers over algorithms and corporations.
• I wanted to better understand my musical preferences. Why do I like/dislike what I like/dislike?
• Andy is a fun person. If he asked me to wait in line with him at the DMV, I’d probably say yes.

But oh, the audacity of it all! Cramming it into a year would require more listening and writing each week than I typically did in several months. It was more than I could commit to.

I politely declined Andy’s offer, but he convinced three others to join him. Each person had a Google doc for posting weekly reviews; each doc was shared out so that others could read and comment. I bookmarked Andy’s doc, followed his weekly updates, and occasionally chimed in from the sidelines.

By late March, the group of four had dwindled to two, leaving only Andy and his neighbor Matt. They’d seemingly found their rhythm, though, and the post-review banter was clearly a lot of fun.

Buoyed by their progress and bored out of my quarantined gourd, I decided to jump in. I started with their current batch of albums (120 down, 380 to go) and figured I could go back to the ones I missed whenever I had time, perhaps even catching up by the end of the year.

It was easy at first. Beginnings are exciting and real-world distractions were few: spring hadn’t fully sprung in Boston and COVID vaccinations weren’t yet widely available.

As the initial excitement wore off and post-vaccination summer arrived in all its glory, I came to realize that the challenge wasn’t in completing a single week, but in completing one week after another for months on end. Our group referred to the challenge as the “RS500” but my private subtitle was “So you think you like music?”

To make up for sagging enthusiasm, I learned how to fit listening and writing into my weekly routine. If I was awake and not otherwise using my ears or brain, I was probably listening (and re-listening) to albums. The RS500 became the soundtrack to nearly every workout, household chore, grocery run, and long drive of 2021.

I tried to be a good student of the music: I wouldn’t skip a track until I’d listened all the way through the album and I listened in single sittings whenever possible. I played through most albums more than once and almost always researched the album and artist before writing up my thoughts.

Making time for writing was relatively easy; the challenge was in coming up with something to say—even if it was just an opinion, observation, or mildly related tangent. This was especially true for albums I felt indifferent about, which was my most common response to the RS500:

My rating	Dislike	Shrug	Like	Love
Album count	100	205	160	35
Examples	“Kid A” – Radiohead “The White Album” – The Beatles “The Chronic” – Dr. Dre	“Blue” – Joni Mitchell “Abbey Road” – The Beatles “Rumours” – Fleetwood Mac	“Horses” – Patti Smith “Baduizm” – Erykah Badu “Live Through This” – Hole	“Diamond Life” – Sade “AM” – Arctic Monkeys “The Anthology” – Muddy Waters

My “reviews” were more like “responses,” sometimes only a sentence long and sometimes having little to do with the music: tangential pop culture references, comments about the album art, inside jokes, and occasional complaints about the RS500 selections.

We all dragged our feet at moments, but we all stuck with it. Andy and Matt finished just before Christmas; I “finished” with them and then circled back to the early albums I missed, completing the challenge 349 days after I’d started.

When all was said and done, Andy and Matt had each written about 250,000 words. They’d ordered their documents by oldest reviews first, meaning that in order to see the latest entries, you’d have to scroll all the way to the bottom of the document. This wasn’t a big deal at first, but snowballed into a comically poor design choice. By the end of the year, their docs took more than a minute to load and would sometimes crash my web browser. Reading their weekly reviews felt like loading a webpage back in 1995. Together they’d written an Infinite Jest worth of text.

By contrast, I wrote only 27,000 words—still more writing than I’d ever done in a year. I’m a “less is more” sort of writer, but I just don’t have the same relationship with music that Andy and Matt do. This is especially true with rock music, which remains over-represented in the RS500 despite the magazine’s multiple efforts to diversify the list.

Am I glad I did it? Uhh, I guess? It was the best bad idea of 2021.

My favorite listens were the albums I’d previously ignored, but ended up loving: Harry Styles’ “Fine Line,” Mariah Carey’s “The Emancipation of Mimi,” Bonnie Raitt’s “Nick of Time.” There were also pleasant surprises like Pink Floyd’s “The Wall,” where I went in with my guard up but came away with sincere appreciation. It’s not every day that our expectations are happily confounded; by sheer volume, the RS500 afforded many such moments.

The sheer volume also exposed the limits to nearly every core motivation that drew me into the challenge, especially my desire to expand and refine my palate:

• The experience helped me appreciate artists and genres outside of my everyday listening, but not as much as I thought it would. I also found that beneath the healthy interest in expanding my horizons, there was an undercurrent of FOMO—a millennial’s obsession with the mythical best. Curiosity is a good thing, but so is contentment. We can find joy in missing out; it gives us more time to enjoy what’s special to us.
• The exercise helped me articulate my preferences, but I caught myself using that newfound language to explain inconsistent (and still opaque) tastes. I was trying too hard to think about something I was supposed to feel.

The only motivation that survived intact was the desire to do something ambitious with friends. The camaraderie was real: we kept each other motivated and accountable; we struggled through Drake’s “If You’re Reading This It’s Too Late” and ABBA’s 147-minute “Definitive Collection”; we cursed the Rolling Stone editorial staff; we cursed ourselves for agreeing to the challenge. If we didn’t have each other, none of us would’ve finished. And even if we had, I don’t think it would’ve meant what it did.

As a personal exercise, the stockpiling of musical knowledge and experience came to feel pretty pointless—too much of a good thing. What never felt pointless was doing something difficult with people I like. I’m well on my way to forgetting most of these albums; I won’t forget tackling the RS500 with Andy and Matt.