It was at least one in the morning and somewhere in Philadelphia I was driving a van full of rappers to an appearance on Philly native and pioneering female emcee Bahamadia’s weekly radio show, B-Sides. This was in late February, 1999. It was cold and damp and I had no cell phone, no GPS. I followed another van filled with still more rappers and driven by an employee of Zero Hour Records, the parent company of 3-2-1 Records, the fledgling New York City hip-hop label for which I was a mere intern.

We were neck deep in a long-weekend tour to promote Skeme Team’s new single, “Plan A.” I was twenty-two, a recent college grad with a B.A. in jazz performance, and I was driving around a bunch of guys who wouldn’t know a whole note from a hole in the ground. Worse, I was doing it for free, out of a love of hip-hop and a naïve assumption that going on tour would be a cool thing. Cool things were the reason I’d moved to New York in the first place.

We were late. We were always late.

The van was filled with smoke and rain fell in thick, fat droplets. On the way from the hotel to the studio, we had already stopped twice for cigarettes and alcohol (once for each van). Sitting in the idling van outside a superette, I had no idea if we were lost. Nobody told me much of anything. I was left alone with the radio, which was blaring the very show that we were so badly late for.

This was the second and final night of a tour that felt like it had been going on for fifteen years. A seemingly endless series of lonely concerts and in-store appearances, culminating here in Philly, was stretching into infinity. All I was there to do was drive the van, but time itself was starting to feel filmy and papery.

But then. As the chunky rain gave way to pillowy snowflakes, the thunderous hip-hop pouring from the shitty speakers broke into something expansive and empty, framed by what sounded like cathedral bells. The beat clicked and sliced, spare and off-kilter, and the bass rode deep beneath it, mournful and resonant. On my frayed nerves it felt like the most beautiful music the world had ever produced.

This. This was what I was chasing by getting into the music industry: those sounds that set hooks in your chest and opened it up.

I had to find out what it was. When we at last arrived in our haphazard fashion, the skinny, bedraggled white dudes who programmed the music made a half-hearted attempt to figure out the name of the song they had played just twenty minutes earlier. One of them held up a light lavender record with a retro photo of a guy in a butterfly collar doing the robot. Superrappin: The Album.

I jotted it down.

*   *   *

The late ’90s were a genuine high-water mark for hip-hop. A quick recap of significant releases from 1998: Goodie Mob’s Still Standing, the Beastie Boys’ Hello Nasty, Lauryn Hill’s The Miseducation of Lauryn Hill, Outkast’s Aquemini, Mos Def and Talib Kweli’s Black Star and Jurassic 5’s self-titled album. Early 1999 saw The Roots release Things Fall Apart and Eminem drop The Slim Shady LP. Hip-hop was expanding and consolidating at the same time. It was easily the most vibrant music being made.

This is what I thought I was getting into at 3-2-1 Records when I signed up for a four- to six-month internship with the promise of some kind of employment afterwards. Although I owned a secondhand beginner’s DJ setup and played guitar in a hip-hop band back in Minnesota, I couldn’t rap and I could barely DJ. But to me it didn’t matter, or at least I thought it didn’t. Music was the great universal, the thing that could break down barriers.

3-2-1 was run by British ex-pat and publicist-turned-label manager Fiona Bloom. It was home to California’s Blackalicious, Atlanta’s Micranots, Chicago’s Rubberoom, Bigg Jus from Company Flow and others. Maybe it wasn’t Rawkus Records, whose Soundbombing compilation had largely introduced me to independent hip-hop, but it was good, and poised for bigger things, with the release of Blacklicious’s domestic debut album Nia slated for that summer.

Skeme Team, a production duo from Staten Island who wore jeans, hoodies and logo-festooned jackets as baggy and voluminous as their facial hair was manicured and tight, had made one good record, heavily indebted to their borough-mates Wu-Tang Clan. The A side, “Con Artists,” was oppressive and claustrophobic, even as the rise and fall of the strings leavened it with a little bittersweetness.

The Skeme Team’s “Con Artists.”

To be honest, I was a little scared of it, and of them. I would have much preferred to hit the road with Gift of Gab and Chief Xcel from Blackalicious. Their brainy, literate music was much more like the hip-hop I listened to than Skeme Team’s, which felt rugged, abrasive — more rap than hip-hop.

The refrain of “Con Artists” was delivered with a gravelly, Method Man-esque cadence:

Skeme Team, even when you know us you don’t really know us

You shouldn’t trust us as far as you can throw us

It turned out to be more than just a clever hook. Fiona told me in no uncertain terms before we left that Skeme Team would do everything they could to turn every situation to their advantage. They were connivers, manipulators. Maybe seeing my concern, she quickly emphasized that they weren’t malicious. Just always on the take, as a lifestyle, a point of pride.

I spent most of the tour trying to avoid directly interacting with them.

*   *  *

By the time we left Bahamadia’s studio, it was well past three in the morning and Wilkins, the only 3-2-1 employee on the tour, had put his foot down about getting back to the hotel. A native New Yorker with family from the Dominican Republic, Wilkins couldn’t have been more than a couple years older than I was but he exuded urban savvy, nonchalantly ordering bodega sandwiches in tight in clipped Spanish, and strolling around the 3-2-1 offices with his sweater off one arm and hiked up on his shoulder. I don’t remember if Wilkins was his first or last name, but I didn’t know him by any other. Then again, I didn’t know the real names of any of the rappers on the tour either. It all made sense at the time.

He was in the other van — the more difficult van — with Skeme Team and some but not all of Non Phixion, who appeared on “14 Years of Rap,” the single’s B-side. My van held Pumpkinhead, Rack-Lo and Thirstin Howl III (who, frankly, had my favorite track of anyone on the tour, “I Still Live With My Moms”).

Thirstin Howl III’s “I Still Live With My Moms.”

With Bahamadia off the air, the stereo had been given back over to endless beat tapes and mixes made by friends of the Skeme Team. I once got up the nerve to slip my band’s tape into the deck, but the light mockery of the rapping was enough for me to eject it after one track. An attempt to play Camp Lo’s Uptown Saturday Night was met with derision.

Camp Lo’s “Luchini.”

“These guys are from the Bronx, right?” they scoffed.

At a light, we pulled up behind an older car, maybe a Taurus or Sable, our stereo blaring. When the light changed, the car in front of us didn’t move. Someone leaned across me and laid on the horn. Nothing.

The other van pulled alongside and then ahead. Wilkins hopped out of the back and went around to the stopped car’s driver side. He peered in through the glass and then banged on the window, waited, then banged again. He walked back to me. I killed the music and rolled down the window.

“Dude’s asleep.” Wilkins looked towards the car and then back at me. He banged on the window again with the flat of his hand. He tried the handle. When the door opened, he shook the driver awake and as soon as he did, the car sped off, right through the light, which had cycled from green to red to green and back to red again.

Wilkins stood for a moment in the street, then got back in the van.

*   *   *

The antagonist of Jonathan Franzen’s novel The Twenty-Seventh City is a corrupt St. Louis police chief whose method for getting what she wants is indirect, yet brutal in its own way. Her network of assistants and associates upend the protagonist’s life in sidelong ways — seducing his wife, killing his dog — in order to break down his sense of control, to wear him away to the point where he has no sense of security.

This was, more or less, Skeme Team’s approach, executed mostly through a consistent and concerted foot-dragging throughout the tour. We were late to our first in-store appearance in Providence. We were late getting to Boston, where we picked up Mr. Lif in front of his apartment. Mr. Lif is a great emcee, but terrible at relaying directions from the wayback of the van. After the in-store (where a performance didn’t even happen because we were late), we got to the venue too late for soundcheck, and then the show started late.

This thorough, pervasive tardiness served as an effective wedge for Skeme Team to get what they wanted, since it was easier for Wilkins to stop when they demanded than to argue with them. But for me, it was torture. I was rabidly, fanatically punctual, in all things, then as now. I believed in preparedness, and had packed clothes for this trip that were carefully calibrated to be hip-hop, but not so hip-hop that I would appear to be trying to be hip-hop: baggy jeans and sweats by Caffeine purchased at Yellow Rat Bastard on Broadway; a black, puffy down jacket; Nike running shoes; a Boston Red Sox fitted hat. Basically, everything I owned that, taken together, would make me look a little less country mouse.

But Skeme Team just stomped all over everything and everyone had to adjust to it. Others in my car had cell phones. I would hear a ring and someone answer, then: “They stopping here” before the van in front of me would pull over into the parking lot of a convenience store or gas station. When our final in-store in Philly looked a little light in terms of audience, they simply left for an hour to find a liquor store.

Just a month and a half into living there, I already had a dim notion that this was part and parcel of succeeding in New York City; that you had to unapologetically fight and claw for your space. This weird mix of torpor and aggressiveness infected my experience of the tour, a blend of molasses and vinegar. As the van driver, I was in the contradictory position of being in charge of getting to where we were going but having absolutely no control over how it happened. As it was with moving to New York to get into the music industry, I felt as if I’d leapt across the gap between two buildings, only to watch the second one move away while I was in midair.

*   *   *

The morning after Bahamadia’s show, we drove around Philly, struggling to find a breakfast joint. Every neighborhood we passed through elicited a familiar reaction from the van’s passengers as they likened every street or building to one they knew from New York. “This looks just like Bed-Stuy,” they said, pointing out the windows at murals or brownstones.

They’d been doing it the whole trip, but it was only then, on that final morning, that it struck me: many of these guys had never been out of New York, or at best no farther than New Jersey.

I doubt they felt as shaky and unsure of themselves as I did almost twenty-four hours a day, but by the end of the tour, I caught glimmers of vulnerability when the light caught just right. I genuinely liked Pumpkinhead and Thirstin, who were both funny and thoughtful, even borderline encouraging to me the few times I talked briefly about music, when they dropped a little of their built-in disdain for my awkward attempts at connection. To a man (and it was all dudes), everyone out on this tour was dealing with his own limitations in various ways. We were just looking at some of them from opposite sides.

We got back to New York late that Sunday evening, and the plan to drop everyone in one spot, from which they could take subways and buses, dissolved. I drove all over Brooklyn, dropping rappers here and there, collecting fist pounds along the way, deep into the night. By the time I returned the van to the off-brand rental place, it was well past midnight and the N was nearly deserted on my ride home. (This was also when I discovered that I’d lost my ATM card somewhere along the way.)

When I walked into my apartment, there was a giant cockroach sitting in the middle of the entryway floor. I un-slung my duffel bag from my shoulder and threw it upward in a generous arc.

It landed directly on the bug and I went to brush my teeth.

*   *   *

It was a month or more before I found Superrappin: The Album on vinyl at Fat Beats on Sixth Avenue. By then, 3-2-1 was working the first release from Rubberoom, Architechnology. The group’s sound was even darker than Skeme Team’s, the music practically post-apocalyptic, and rappers Meta-Mo and Lumba were grim and unyielding on the record. But in person they were friendly and willing to work hard for their music.

I slit the plastic wrap down the side of the Superrappin double vinyl and cued it up on one of my turntables. It was (and still is) a terrific compilation, with artists like Rasco, The High & Mighty, Pharoahe Monch and Shabaam Sahdeeq gliding over retro soul beats grounded in trebly guitar squawks, milky vibraphone and organ, and blasts of horn.

Suprerappin’s “Walkin’ Large.”

But I grew impatient, eventually skipping to each new track in search of the cut I’d heard in the van that night.

It wasn’t there.

I was on the cusp of getting a paid position with 3-2-1 a few months later when I came into work and found everyone emptying their desks. Over the weekend, one of the label’s partners — who controlled 85% of the money — had decided to quit the music industry. Blackalicious’s debut would be handled by another label. The operation limped on with a skeleton crew for a month or two, and then dissolved, disappearing like that song, like my ATM card, like the entire tour.

Sometimes, on the way to figuring out who we are, we find barriers instead of the revelations we expect; we discover that we can’t become new and different people just because we want to. Right now, my two-year-old daughter wants to be read The Missing Piece by Shel Silverstein before bed every night. I like the part that goes, “So on and on it rolled. Having adventures, falling into holes, and bumping into stone walls.” I know just how it feels.

*   *  *

Steve McPherson is a writer and musician whose work has appeared in Grantland, the New York Times, the Classical and elsewhere. He lives in Minneapolis and you can follow him on Twitter (@steventurous).

Nate Beaty draws comics and codes websites and gulps gallons of green tea in his multi-cat Chicago home.