90 Songs That Explain My 90's: Volume III
Inspired by Rob Harvila’s podcast (and now book) 60 Songs That Explain The ‘90s, in which he reads sprawling and personal and funny and weird and rambling essays about songs he believes explain how the 90’s were, I thought I’d write my own version: 90 Songs That Explain My ‘90s. Emphasis on MY.
I promised no sprawling essays, though. Blurbs, I said, just blurbs. Or essay-sized blurbs. But that’s been more of a nice thought than an actual execution.
As always, you can listen along via playlists on Spotify or on Apple Music, should you desire to follow along at home.
12. Elliott Smith- Waltz #2 (1998)
Ladies and gentlemen, the precise axis-center point1 of my lifelong Beatles axis and my 90’s indie rock axis. Elliott is a spiritual grandson of all of the Beatles in composite, and a spiritual grandfather to modern melodic melancholy like Phoebe Bridgers, who is on the record as a huge fan.
Fact: Elliott has better songs than “Waltz #22”, but this is the song that sealed the deal for me with its titular loping waltz, its understatedly hooky chorus, its rising verse melody, and of course Elliott’s lyrics, presumably at least partially about a night of passive-aggressive karaoke between his mother and maybe his stepfather?
First:
First the mic, then a half cigarette / Singing "Cathy's Clown" / That's the man she's married to now / That's the girl that he takes around town
Then the man gets his turn on the mic:
Here it is / the revenge to the tune of “You’re No Good”3 / You’re no good, you’re no good, you’re no good.
On brand for Elliott, he doesn’t tell you the whole story in laborious detail. Instead, he lays out snapshots. Gives you little slices. A line of dialogue. A song title (or two) that do some heavy lifting. It takes vision and guts and a solid internal editor to leave stuff out, to believe in the power of less-is-more, and Elliott does.
Musically, Waltz #2 is a demarcation point for me, personally and musically. A cairn on the path of the songwriter I would become. Well into the late-90’s, I was playing electric guitar and bass in what I would probably categorize as a jamband. We were Big Head Todd/Dave Matthews/Widespread Panic/The Samples adjacent, I guess, with some trace elements of ska (we all worshipped local ska gods Swim Herschel Swim as well as the Bosstones) as well as some, um, experimental forays into groove-driven rap rock (a la Rage Against The Machine, Beastie Boys, 311 but decidedly not Limp Bizkit, just to be totally clear). I was moonlighting, though, writing quiet/sad acoustic songs late at night in my bedroom that pretty much nobody would ever hear.
It dawned on me today, just now, that Elliott Smith did the same thing (albeit with a much cooler band—Heatmiser—that trafficked in neither ska nor “groove-driven rap rock”), making his quieter music privately on the side (albeit more critically acclaimed).
So hearing Elliott Smith’s music—the quiet bedroom stuff—opened up possibility. And hearing Elliott Smith’s music—the more band-oriented, Beatlesy stuff—made me realize I didn’t have to pick a side. I could do both. And that’s just sonically speaking, saying nothing of the impact his songwriting had on me, which was massive.
Having written and released and performed my own music now for over 20 years, I’ve grappled time and again with the marketing necessity of genre categorization. People—journalists, promoters, streaming services, even fans—want to put you in a box because it makes it easier to parse. I never felt like my music fit tidily in any of the boxes4, but I played the game because that’s what you do; you have to have an artist bio and whatever story you conjure to try to make a stranger care. Some genres I flirted with:
singer/songwriter
folk
folk-rock
graveyard folk
americana
alt-country
alt-folk
neo-Beatle-esque
post-Beatles Americana5
indie6
indie folk
None of them feels particularly right (or necessarily wrong, for that matter). Just…inadequate.
Ultimately, I think I want to make records in the genre of Elliott Smith (and his grandparents The Beatles, and granddaughter Phoebe, and genre-agnostic artists like Neil Finn, Elvis Costello, Joe Henry, Sparklehorse, Fiona Apple, etc.) Great songs with thoughtful lyrics and ample heart as well as harmonic and melodic surprises. Room for quiet acoustic songs. Room for bigger, louder stuff. A rarefied sweet spot, yes. Which explains why there was only one Elliott Smith. What a loss.
13. Sheryl Crow- If It Makes You Happy (1996)
I’ve already posted about my love for Sheryl, but let me reiterate: I’ll go to bat—no, I’ll swing for the almighty fences; no! I’ll steal all the bases and home too; no! I’ll lift the entire ballpark up and spin it haphazardly on my pinky finger!—for Sheryl Crow’s first three albums all day, every day. I’ve even made a case for the fourth one having good songs that were, to my ears, produced sub-optimally. (Too slick. Too compressed. Too much.)
Like with Elliott Smith, this song isn’t my favorite Sheryl Crow song or even my favorite album (The Globe Sessions) of hers, but it captures a lot of what makes her great: sprinkling the everyday (“scrape the mold off your bread”) in with tossed-off, image-strong pop culture references (“Geronimo’s rifle and Benny Goodman’s corset”), a way with words, a catchy-as-all-get-out chorus both melodically (the moment reaches for the stars and achieves escape velocity!) and lyrically (its concise bumperstickerability!), a bit of disillusionment (“played for mosquitoes” aka bloodsuckers) mixed with hope (“I told you I’d never give up”). And that raspy voice, man!
14. Cracker- Low (1993)
Pardon the superlative but here goes nothing: Cracker is the most underrated band of the 90’s7.
Principal songwriter and singer David Lowery can pull off the irony and the hipster winks and downright left field weirdness that Stephen Malkmus dreams of while also being nakedly earnest and writing rich imagery. Like, just get a load of some of these lyrics:
You'll be a Russian acrobat / You'll be like Burt Bacharach / You come to the party, you say 'What's new pussycat?
Hey, June, why'd you have to come? / Why'd you have to come around so soon? / I wasn't ready for all this nature / The terrible green, green grass / The violent blooms of flower dresses / And afternoons that make me sleepy
I tried dating a mermaid / She buys pot from the first mate / That mysterious cargo
is still guarded by monkeys
Somewhere I failed / Somewhere I lost you /In a black crowd of crows / And shiny things I can't remember
I know the whiskey, it won't soothe my soul / And the morphine won't heal my heart / But if you take me down to the infirmary / I won't have to sleep or drink alone
One of my favorite lyrics might not even be Lowery’s official words. From that last song, “Take Me Down To The Infirmary”, I’ve always heard the second verse as “Take me down to the infirmary. The walker sound is as blue as her eyes.” Like the squeaking wheels of somebody’s walker rolling down the halls was depressing. Genius.com tells me that’s not the line at all, but I don’t care. It’s the line to me.
And that’s just Lowery, no mention of his guitar-slinging compatriot Johnny Hickman. A guitar hero in the classic Les Paul-driven mold. The band, speaking of genrelessness, is rock, country, blues, Americana, polka, alternative, indie8, all of it. Like with Sheryl & Elliott, this song isn’t even my favorite Cracker tune, I could easily pick 15 songs.
Cracker is the real deal. I understand why disposable sugar-high pop like Sugar Ray got commercially bigger than Cracker, but that doesn’t mean I have to like it.
15. Morphine- Cure For Pain (1993)
“You’ve never heard a band like this,” people say and then play you a song by some band that sounds a lot like….a lot of other bands.
Morphine, though. MORPHINE, THOUGH! Morphine is one of the rare bands where it might actually be true, at least as far as rock bands go.
First, at the center, you’ve got this guy with his bass-y drone of a beat poet voice playing a murky, prowling two-string9 electric bass guitar (often with a….slide?!?) and singing songs that feel like dark short stories. Then you’ve got this jazz-inflected drummer, keeping things sizzling, crackling like a lightbulb breaking in real-time, without ever calling attention to himself. And the last piece? A saxophonist, who sometimes plays two saxes at once, wailing here, honking there, picking his spots, like the lead guitarist in any other band (and like the horn section, duh). The whole thing would stink of gimmickry if the band wasn’t so good and so real. Morphine was my first real taste of noir as an artistic choice.
You’ve never heard a band like this. For real.
16. Doo Wop- Ms. Lauryn Hill (1998)

The question I heard most, while working as a clerk at Tower Records in Boston during the spring and summer of 1998 was:
“Do you have the new Lauryn Hill?”
By a landslide.
The first time I heard the question, I responded, “the new what?” The asker’s face was perplexed. I suppose she may have thought I was struggling to understand her heavy Boston accent, but I think she just thought I was stupid, a recently unfrozen Pollyanna Captain America culturally oblivious to a gigantic star. But I couldn’t fake it: the name meant nothing to me.
The second time I fielded the question, I knew enough to say, “It hasn’t been released yet.” But this time I found myself, immediately, hurrying behind the checkout counter and asking one of my co-workers, “Um, so…who’s Lauryn Hill?”
The co-worker laughed, like I had to be kidding. I was not kidding.
See, what happens when you go on an LDS mission—especially a foreign mission, pre-internet—is that you are swallowed up by a two-year pop culture black hole. Things that happen in pop culture during those two years are lost (at least temporarily), redacted from your document. Serving in Brazil where not every single piece of pop culture was the same as in the U.S. and where even just mail took weeks to arrive (if it ever arrived) highlighted it all the more. Sure, as I walked the streets of São Paulo in my shirt and tie, I heard the unavoidable world-conquering Spice Girls and whatever the massive Celine Dion song of 1996 was. I even heard The Fugees’ cover of “Killing Me Softly” now and then, though I never knew the name of the group, much less their lead singer, Lauryn Hill.
When I exited my proverbial black hole in the latter half of 1997, I caught up on a lot of what I’d missed, the music in particular—Soundgarden’s Down On The Upside10, Counting Crows’ Recovering The Satellites11, Beck’s Odelay, Dave Matthews Band’s Crash, Sheryl Crow’s second album (see above), Fiona Apple’s Tidal, and The Wallflowers’ Bringing Down The Horse were some of the big albums I devoured. But, to this day, there are still some rather egregious mission-induced pop culture blindspots for me, a sealed black box of media. Let’s see…to this day, I’ve still never seen big-at-the-time movies like Seven, Tombstone, Trainspotting, 12 Monkeys, Space Jam, Evita, Sling Blade, The English Patient, The Hunchback of Notre Dame, Waterworld, Die Hard With A Vengeance, The Nutty Professor12, or Pulp Fiction (the latter I have seen in pieces, but never in one sitting). I had never listened to Outkast’s breakout album ATLiens until last year. I still haven’t sat all the way through Sublime’s first album. I basically missed the popular apex of Tupac and Notorious B.I.G.
All of this to say that Ms. Lauryn Hill—by name, at least—resided in that same black hole. At least she had Biggie and Madonna and Tarantino to keep things interesting in there.
After my coworker stopped laughing and realized I was not being funny, he asked me, sarcastically, if they played black music back in Utah. (He may as well have called me a hayseed at that point.) I said they did, though probably not as much as in Boston.
“So you never heard the Fugees, my man?” he asked, eyes skeptical, “Like ‘Fu-Gee-La’ or or ‘Ready Or Not’?” My insecure eyes told him both, “No” and “But I really wish right now I did.” His Hail Mary question was, “What about ‘Killing Me Softly’, you know… (he sang) ‘Strumming my pain with his fingers…’”
A flash of recognition. The connection. The din from blown-out speakers on the streets of São Paulo. He was as relieved as I was. “That’s Lauryn Hill.”
Her debut solo album, The Miseducation of Lauryn Hill, finally came out a month or so later. Tower Records was packed. We couldn’t keep enough CDs stocked on the shelves. It was the hottest thing we had.
And for good reason. Lauryn Hill was a generational talent and her debut album was generational too, combining classic R&B with modern hip hop. She was one of the first real twofers (singer + rapper, and devastating at both). There were hints that she might be an all-timer, but we didn’t know it just yet. Still catching up from the black hole, I especially didn’t know it then. But we all know it now.
What we couldn’t know was that it would be her only studio album13. So far, that is.
Jon Brion and Aimee Mann aren’t far off, though. And just outside of that, you’ve got Flaming Lips, World Party, Big Star. And over there, near the pop/rock quadrant…. probably XTC, ELO, and Oasis?
My favorites in no conscious order:
Stupidity Tries
Needle In The Hay
Between The Bars
Bottle Up & Explode
Say Yes
Ballad of Big Nothing
Angeles
Miss Misery
LA
Son of Sam
Happiness
Alameda
Easy Way Out
Even just Elliott’s using other songs’ titles in his songs has seeped into the songwriting of the songwriters who adore him. This year alone on their debut album, the supergroup boygenius has songs that, both overtly and subtly, namedrop:
Boys Don’t Cry by The Cure
Leonard Cohen
This Love by Taylor Swift
Rainer Maria’s Letter To A Young Poet
This is not a Whitman-esque I Contain Multitudes boast of “oh, I’m just too multi-faceted to be pinned down by your puny genres.” I just don’t feel like I’ve ever really fit nicely into any of them.
Not folk enough for the purebred folkies.
I’m not loud enough for rockers.
Not dangerous enough for the punks.
I don’t pop enough for poppers.
Not modern enough for the mods.
Not soulful enough for the Neo-soul-bros.
Not edgy enough for the edge lords.
Not twangy or dusty enough for the Americana world.
Not dranky enough for the bar.
Not poetic enough for the coffeehouse. (Besides I drink Diet Coke for my caffeine.)
I don’t ruin the song enough for art rock.
I once used this descriptor when meeting with a Nashville publisher, when my music interests were leaning more classic country and alt-country. He got it immediately, which felt good. “Right, so more chords. More range.” Yep.
Don’t get me started on “indie” as a genre. Let’s just say: I didn’t start the term. I just briefly employed it because it helped as a shorthand for “not pop” for awhile when I was booking tours on the west coast.
Today at least. I could also argue for:
Living Colour (though their breakthrough album was in the 80s, I think)
Superdrag
Nada Surf (hurt by an early hit that’s not representative of their catalog)
Blind Melon (same)
Brad
Swim Herschel Swim (I will always maintain that if they had held on two years longer, they would’ve been as big as any of the Reel Big Fishes that hit with the ska revival)
Morphine (more on them in a second)
Sparklehorse
The Sundays
Jayhawks
Los Lobos
Grant Lee Buffalo
There it is again. Against my better judgment.
Traditional bass guitars have four strings. The modern thing is to add strings (5- and 6-string basses are common. 2-string basses are not.)
The first song I listened to after my two-year music fast? “Blow Up The Outside World” by Soundgarden, as curated by my younger brother Andy, who came with my parents to pick me up in Brazil. After two years of listening only to gospel hymns and the happenstance music blaring out in the streets, my system was not ready for the heaviness of Soundgarden.
Soundgarden being too much too soon, Andy eased me back into pop culture with “Catapult” from Counting Crows’ sophomore album.
I didn’t say GREAT movies. Just that all the movies listed were either critically acclaimed or grossed over $200M worldwide.
Her live Unplugged album has original Lauryn Hill songs on it, but I don’t count it as a studio album, good as it is.