Playlist: Early 2000s Underground Hip Hop

Posted on Jan 6, 2024

In 2003, I was 19 years old, and on the verge of completing something. I didn’t know it yet. I didn’t realize I had a project at all.

What was this project? Well, I was trying to listen to music I liked, as much as possible. I was getting it pretty well figured out through trial and error triangulation - do I like this? How far off is it? Do they have anything else? By 2004, I’d gotten as close as I could get. I had hit diminishing returns, and I stagnated for a while, and then I changed.

My music listening technology back then required a lot of small chores. I could fit about 90 minutes of music onto my small non-iPod MP3 player. I could keep a lean collection of CDs in the console of my car.

It took effort to find new music, and I put a lot of effort in. Listening and assessing. I kept tabs on a lot of things that I thought were noteworthy or interesting, but kept a shorter list of more precious favorites.

Back then, I was drawing from a particular well of sources. I found music by reading reviews online, or by looking up a featured artist from one track to dig up their solo work. I didn’t realize at the time that this process mostly kept me in the underground hip hop lane that I was already in. It wasn’t comprehensive, but I was thorough about the process, and I enjoyed the love and intention it involved.

I like melodic riffs with a lot of texture and atmosphere, exactly the kinds of things hip hop producers like to select as samples. I also like earned confidence. Underground hip hop met me where I was at. Like me, it was concerned with personal ethics and righteousness. Like me, it was proud, and aspiring to greatness, but dealing with an aversion to mainstream popular culture. It could be explosive and dancable, but it was also trying to be quotable, a better fit for headphones or road trips than for parties.

I hadn’t figured out how to listen to and enjoy other lanes of hip-hop. I had ATLiens languishing in a drawer next to Only Built for Cuban Lynx, and plenty of others. To be honest, I still find both of those albums difficult.

But soon I did branch out. By 2003, I was no longer getting what I wanted from indie rap music. I was digging into more and more obscure releases, and it was starting to feel like a chore. Spend long enough listening to a lot of people working from the same influences and shooting for the same stars, and innocent conventions become clichés. Finally, I heard Jay Z’s The Blueprint in Spring 2004 (2.5 years after it came out), and that changed my attitude toward mainstream rap entirely. Then in 2005 Saul Williams said the exact right thing:

But this ain’t for the underground
This here is for the sun 1

Let’s trample over the idea of underground music - I want more people to hear some of these songs. I don’t want to be one of a small number of people who know about Jean Grae, or a select few who know how great Hi Tek is.

At the time, I wouldn’t have thought to commit my indie rap vibe to posterity. But even when I wasn’t listening to that music regularly anymore, it still fed my imagination. The little machine in my brain that I trained back then continues to listen in on all my musical stimuli and measure them against the classics 2. I’ll still hear snippets in my head during daydreams. It is a quietly influential set of expectations that I have often struggled to understand myself, much less explain to others.

Please accept this invitation to explore a space within hip hop that I know in detail.

Song List

Listen on YouTube

Musical experiences are private, even if you want to share them. I guarantee that there’s magic in each of these chosen tracks. If it’s not obvious to your ear at first, reading a few words about the song may unlock what it holds.

“Don’t Rush Me” - Jean Grae

On other songs, in her battle-rap mode, Jean Grae can be pretty terrifying. Her imagery is intense and delivered with precise timing, like in this guest verse on “The Illest”:

Swiftest stealth assassin
snipe you from balcony shots
A terrorist position, professional
from the opera box

Instead of a battle rap, “Don’t Rush Me” is a track about self-improvement. Producer 9th wonder gives her a hammering keyboard bassline to build over, rounded out with supportive vocal oohs and ahs. The hook is defensive, demanding space, fending off criticism. But she spends each verse talking herself up, checking bad impulses and committing to optimism.

I yell too much
Get stressed too quick
but the best thing about it?
I can change that shit

“Certified” - Diverse

Sometimes folks will talk about a rapper “using their voice as an instrument”. In theory, it should be a compliment, but in context it tends not to sound like one - folks say it about rappers with memorable delivery, but who aren’t known for quotable verses. In the mix of “Certified”, Diverse’s vocals are quiet - I think it reflects a commitment to the musicality of the song, and awareness of how much attention that guitar riff demands. He packs a lot of words into each bar, and he patters over his punchlines instead of spotlighting them.

It goes around like bad karma with mass trauma, the 12003
Yo, who want it? Cause I’m much obliged to give it
With centrifugal forces, sources beyond your physics
My mic chemistry, convincingly providin’ what’s efficiently fly

“Spaceman” - Non Prophets

Many of Sage Francis’s songs seem to be willfully hanging out in their own anger and gloom. But just when you might be drifting off, thinking maybe he’s a little dark for you, he’ll effortlessly deliver a twisty passage with alliteration and unexpected rhymes.

single-celled amoebas
evolved into simpletons
singing jingle bells for Jesus

not to knock the teachings Jesus brings
cause The Bible’s a good read
like Stephen King’s needful things

“Scratch Rappin” - Hi Tek

Hi Tek worked with Mos Def and Talib Kweli on the Blackstar album, and with Kweli again on the Reflection Eternal album, before becoming a house producer for Aftermath and releasing a series of “Hi Teknology” solo albums.

The introduction to the first Hi Teknology, the concept of “Scratch Rappin” could have been cheesy, but the verse he pieces together from emcee samples is clever, and each voice that shows up is a happy surprise.

“Neptune’s Jewels” - Mystic

There are lots of rapped love songs, but most have a laid-back delivery, like “Bonita Applebum”, “Song Cry”, or “Passin Me By”. “Neptune’s Jewels” is delivered with full speed and intensity. The energy makes sense - it matches the tension of the unresolved love story, the life or death conviction of Mystic’s character.

I love it for two things - one is the perfection of the timing of a short set of bars:

top priority? believe you me,
like: love, how you feel?
You aight?
What you need?

The other is a guitar flourish that peeks out between the verses and choruses every so often.

“Storm Returns” - Prefuse 73

Sitting in the music of the 2000s, most hip-hop beats were sample based, just like they had been from the beginning, but sampling was also starting to get weirder and further removed from looping records on turntables. J Dilla was chopping records down to single notes and reassembling them as new melodies. Prefuse 73 was also chopping and creating weird rhythms and glitchy sounds. This track comes from Prefuse’s One Word Extinguisher, which is a bit like J Dilla’s Donuts, or even Afrika Bambaataa’s “Looking for The Perfect Beat” from 1982. It changes rhythms and timing constantly - staying with one idea long enough to capture a few bars of it, then grabbing the next one before it floats away. Almost the opposite the traditional looping of a riff.

“Speed” - Little Brother

Little Brother is a group, and its core members are emcees Phonte and Big Pooh. The 2000s, relative to both the 90s and to today, were not a heyday for the emcee duo format. Some of the most prominent 80s and 90s hip hop songs were by emcee duos: Run DMC, A Tribe Called Quest, EPMD. Run The Jewels brought the format back in the 2010s. In between, even though a ton of classic hip hop was made in the 2000s, duos like Little Brother were rare.

Duos are a great format because they create the opportunity for chemistry and contrast between the emcees. In Little Brother, Phonte will often use a whole verse building up to a showstopper punchline

I take this shit personally
I’m making moves but this treadmill lifestyle ain’t working for me
It’s from the crib to the lab to the job to make a profit
And at the days end still ain’t got nothing accomplished

Big Pooh will rattle off brisk lines that build a lyrical and rhythmic symmetry.

Spending time on this pipeline
85 North it’s like mine, going 85 to light minds
Going 95 to take time
Spending days in the rays of the sunshine
Many days those same rays went undefined
Now 40 East is where I go to have my best times
Three lanes going sixty to perfect rhymes

“Pay Them Back” - Brother Ali

I sometimes wonder what experiences motivated Ali to create this song. It must have been disturbing. Ali, a white emcee, confronts other white emcees, knowing that most of the fan base listing, too, is white. And what’s the future of Ali’s vision? Is he a mediator between the “you” and the “them”?

You love this human expression
and they gave you that
So the least you can do is try and pay them back

After this, he invites listeners to create again with humility.

You are not the first.
You will not be the last.
Contribute. Do your shit.
Step the fuck off.
You are not half as important as you think you are.

Producer Ant’s work on this track is epic – the opening tangle of vocal samples – are they both vocals, or did he blend a string sample seamlessly into a vocal?

“Travelin’ Man” - Mos Def & DJ Honda

Mos Def (now Yasiin Bey) was my first favorite rapper, and I still sit on the edge of my seat any time I hear a new verse from him.

This track with DJ Honda is a sentimental favorite of mine - his verse about returning home after a long tour isn’t one of his most famous, but it deserves to be better known.

My hometown is like a whole different scenery
The old timers on the stoop leanin’ leisurely
the new jacks up in the park smoking greenery
easily taken for granted when you up in it
but it’s sweet scented
when you been down for a minute

“Pentagram” - Prefuse 73

I don’t know the story behind this track title. From what I can tell, there’s nothing demonic in sight. But maybe Prefuse is summoning something, or leveling an accusation of ill intent at someone else. Unlike the other tracks on One Word Extinguisher, this one settles down and holds onto an idea long enough to explore it to the end.

“Tony Guitar Watson” - Hi Tek

Hi Tek’s signature sound uses more guitar and bass guitar samples than most hip hop tracks. The plucked strings give Hi Tek’s beats a snap that sets them apart from iconic sounds like Pete Rock’s smoky jazz clubs or DJ Premier’s grand entrances.

I love the crawling funk guitar of this instrumental, and the rare use of cymbals that crash through the drum sequence every few bars. Tony Guitar Watson is one of my favorite beats, and I let it play us out here.

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  3. A “1200” is a Technics SL-1200 turntable. The 1200 is the most celebrated of the small number of turntable models that work well for live DJ, scratching, and hip hop production. ↩︎