(Some of) The Greatest Albums of 1999

Featuring: Fiona Apple, Blur, Blink-182, Mos Def, The Roots, Muse, Red Hot Chili Peppers

The biggest headache of looking at music of 25+ years ago is the sheer volume of awesome stuff that’s lasted and grown in stature in society’s collective musical mind. It’s such a fun problem, but narrowing it down to few enough that I can actually get my ADHD self to write about the many I’ve enjoyed. The perception of this music has aged like wine, and just like when I’m sitting at an Italian restaurant stuttering and stammering as I try to decode the most basic wine list, I don’t always know where to start. This is the end of the 90’s, the beginning of the decade when I actually started to grow into a music taste of my own in the 2000’s. Some of this music I heard contemporaneously, some I heard later as I realized what I’d missed. But it’s all been a ton of fun to revisit.

Welcome back to 1999! And as always, let me know about your favorites that I missed! I’ll add them to the playlist and we can jam in the year 1999 until the inevitable rise of the machines, which in 2025 is somehow even more likely than the Y2K doom scare ever was.

Fiona Apple - When the Pawn…

An absolute powerhouse of an album that I was certainly too young to appreciate in 1999. Even now I feel a little bit under-prepared for the force of the songs, the sometimes grimy and sometimes sultry speakeasy jams. Even the album’s title, in reality a 444-character poem, is an expression of deep frustration of the attempts of the media to change people, while simultaneously introducing a work of art that is powerful enough to bring about the very change in its listeners that Fiona warned us against.

Blink-182 - Enema of the State

It’s funny how much I enjoy this album of pop-punk upbeat whininess when I seem to dismiss the same kind of complainy poor-teenage-me music coming out in 2025. Nobody gets me/romantic frustration/general hormonal anger is timeless, in theory, but in execution the music somehow only seems to translate to those going through the exact same thing at the exact same time. My resolution is not to become one of those “my generation had it worse” people and simply enjoy the entertaining fact that every group of kids has to express the same things in a different way, and the fact that I don’t get the new version is the entire point of creating a new version.

Blur - 13

I guess it was a trend in the late 90’s for alt rock bands to explore new directions, and who can blame them - electronic music was taking off, and Britpop was fading from the mainstream, so what better way to reinvent your sound? This album shows, to me, a perfect example of a band doing just that - morphing their sound to fit the times - without losing their entire identity doing so. This isn’t a Radiohead transformation, a statement I mean as a positive, this is more like changing the way you season your chicken. Whether it’s covered in salt pepper and garlic, or you go with something different like Teriyaki sauce, it’s still the same meat underneath. Blur is some of my favorite British alt rock, and this album is still “them” despite the experimentation.

Mos Def - Black On Both Sides

It seems inexplicable that I would have so little knowledge of this album until now. As I get deeper into my examination of the musical zeitgeist of the years in which I grew up, I start thinking I’ve heard of or at least tangentially absorbed most of the great albums of the time. But then something like this comes around, an album universally loved by critics, a massive commercial success, and I realize how deep the catalog of great 90’s artists actually is.

I don’t think I’m going to come up with any new genius words to capture the greatness on display here. But this album checks all my boxes for great hip-hop; smooth delivery, great beats with a perfect amount of laid-back-ness, intelligent social commentary with an undercurrent of positivity, lyrics with just the right level of density that almost require studying to fully appreciate but not quite. The songs cover everything from women to the environmental crisis to the fact that the Rolling Stones didn’t invent the blues (“Bo Diddley is rock ‘n roll” indeed). That, plus the live instrumentation in an age when even the guitar-obsessed alt rock bands were going electronic, make this an all-timer.

The Roots - Things Fall Apart

Another amazing hip-hop album focused on live instrumentation over loops. Hearing this album back to back with Black On Both Sodes reminds me of the state of most art in 2025, a time when the battle between human and non-human created art is hotter than ever. There was kind of an electronic music advent going on in the late 90’s, and the Roots’ focus on actual honest-to-goodness instruments, of all things, feels more like an act of rebellion rather than a simple return to music’s, well, roots.

Muse - Showbiz

Muse’s debut album is like a stadium-sized circus sideshow soundtrack, with the slow build vocals and crescendoing arrangements perfectly in tune with one another. For a debut they have a ton of poise, like they’ve been honing their sound in front of big crowds rather than the English club scene. I’ve seen the band compared to Radiohead, but I won’t tolerate such slander in this newsletter. Muse’s distinctive sound has always been theirs alone, pretty much from day 1. And even better, to me, Muse sounds like a band of consummate music fans - they seem to have had influences all over the place. This was a gem.

Red Hot Chili Peppers - Californication

By the time I was 10 I could probably recite every lyric from this album. It’s one of the first albums that convinced me that just listening to Greatest Hits albums, which I’ll admit was my main strategy at that age in order to maximize how much music I could get for my allowance, wasn’t actually the best use of my listening time. And fine, not every song here is a banger, but the first 11 inarguably are, and that’s an absolutely massive number of classics for one album. This was RHCP’s peak, in my mind, when their oddball fusion and weird high-guy philosophizing mixed with John Frusciante’s chops to make this a consummate 90’s kid rite-of-passage album.