Don’t let the green grass fool you: The Roots are one of the most respected hip-hop acts in the world; why can’t they leave the sad stuff alone?

Ahmir Thompson and Tariq Trotter. (Michael T. Regan)
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When people ask me now what it was like working for The Roots I am reminded of something Joan Didion wrote: "Spending time with music people was confusing, and required a more fluid and ultimately a more passive approach than I ever acquired."

The entire time I worked in the music industry, three years give or take, I was hopelessly bad at it. The work could be mind-numbing and it seemed full of the agony of waiting. Waiting for the show to start, waiting for the food delivery to come, waiting for the venue to hand over the wristbands.

But on a deeper level, I think I was waiting for them, The Roots, to make an album that felt as alive and sensitive, and as classic, as Organix (1993), Do You Want More?!!!??! (1995), Illadelph Halflife (1996) and Things Fall Apart (1999). I wanted to witness that because those albums changed my life, those are the albums that got me involved in the music industry in the first place.

Undun, however, their 13th record, is the record that makes me want to tell about how The Roots came to be, about how I came to know them, and how they came to make the album that should define their career.

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Ten years ago, I remember believing that Black music was on the brink of some kind of quixotic movement, born out of a vague but collective desire for something "real." I imagine it came from being a generation exhausted by the high price of hip-hop and how bloodthirsty the music had become (Tupac and Biggie were priceless losses).

Borrowing cues from our parents’ youth, people returned to wearing their natural hair, piecemealed-together clothing, and singing heady proclamations about keeping it real. The only failure was that while the soul music of the '70s was rooted in the politics and the spirit of strife, the neo-soul of the late '90s lacked any real weight; its inchoate ideas about consciousness sounded good, and seemed to say everything yet nothing at all.

I remember watching a music video by India.Arie for her song "Video" where the chorus describes all the ways she’s not the sort of girl from a video. These are the sort of things people said, and we listened, and our attention to them and our desire for something seemed to authenticate everything.

So I dropped out of college, locked my hair, and decided that even if I didn’t know what I was doing, whatever was going on in the Roots crew could teach me something about being black and left of center in America. I made a career out of a somewhat naïve belief.

The Roots released Things Fall Apart in 1999 to great critical acclaim. Although it was a departure from their more melodic, jazzy work, it was loud and urgent. From then on The Roots’ albums have ranged from excellent (How I Got Over) to middling (The Tipping Point), but in my mind none captured the spirit of those early records. And so I waited.

Undun, their first concept album, tells in reverse the life of Redford Stephens. Stephens, a mid-level drug dealer, despite being young and smart, finds that his brain is a weak pawn to the pressurized net of racism. Still, Stephens, wanting more with less, plays a one-sided chess game against life until he is sacrificed to the streets.

Undun is not just a very good album; it is, to me, the Roots’ most thoughtful, important album. It does what we expect great albums to do, what Public Enemy’s It Takes a Nation of Millions to Hold Us Back or Prince’s Sign o’ The Times or Sly and the Family Stone’s There’s a Riot Goin' On all do: It tells a story that we rarely hear.

Like those albums, undun is tasked not just with being music but also with delivering up a counternarrative. What it produces is an elegy for a group of men whom America has largely forgotten. And I suspect that when we look back on these strange years of our first black presidency, during which nearly half of all young black men who do not have high-school diplomas also do not have jobs, when one in five black homeowners in America is living under the threat of foreclosure, when the execution of Troy Davis, an almost certainly innocent black man, shifted the international gaze to our deeply flawed justice system—well, I suspect that once the "post-racial" rug that poor black Americans have been swept under is lifted, undun will be the record that reminded us to watch not the throne but the streets instead.

In the summer of 2000, my mother drove me to meet Richard Nichols. I was 18 years old. Nichols is the longtime manager of The Roots, a job he describes as being like the speechwriter for their presidency. After spending four years at a private, repressive high school in Philadelphia that I hated, I saw the Roots, with their intellect, their avant-gardism, and their proximity, as a means of escape. At a job talk at my high school I met an NPR radio producer, Steve Rowland, who was friends with them, and recognizing Providence hearing my call I cut class to talk with him about Frank Zappa and Miles Davis in my school’s parking lot. The result of the conversation was a phone number for Nichols.

I would call Nichols at least four times before he agreed to meet me at The Five Spot, a club in Philadelphia where The Roots hosted a showcase called The Black Lily. I never told him it would be my first time in a bar and I never told my mother it was a bar—I called it "a performance-arts space."

I ARRIVED AT THE FIVE SPOT IN THE EARLY EVENING. The club was empty and the red vinyl décor looked sleazy and tired in the fading light. Nichols, who has the hair of Basquiat and the bearing of Paul Robeson (with a bit more girth), asked me what I was I was trying to do. I made up something about working with the next Harlem Renaissance and keeping hip-hop alive. He listened, told me I was cool, and then explained that he couldn't pay me. I told him that was fine, I could intern. He said the band was going on tour to Europe for three weeks and he would hit me up when they got back.

"Until then", he said, "you can stick around the club tonight if you want. Do you drink?"

"No," I said.

"Well, You’ll get into something. What else do you do?"

"I smoked pot once."

"I’m not talking about that, I mean you sing or anything? What do you do?"

I was thrown. I had been cast as Sojourner Truth in my high-school musical, against my wishes. After the play a few friends praised my acting but little was said about my singing. So I told Richard the one thing that came to mind that was true.

"I write."

"You write?"

"Yeah," I said, and followed with a pointless lie: "I’ve published in a few places and stuff…"

"Not a lot of niggas write," he said. "There you go, you’ve already made yourself useful. I’ll call you in a few weeks."

Nichols, who is surprisingly light on his feet for his a man of his size, hefted a huge backpack over his shoulder and was gone. In what seemed like a few minutes the club got full, the lighting made love to the vinyl, and everything started to gleam. I sat by myself shredding napkins into snow and experienced The Black Lily.

Nichols, his wife Mercedes Martinez, and Tracey Moore, who together formed the singing duo The JazzyFatNastees, created the showcase to give a platform to women in music, but it acted as a hub for something much larger. The crowd was theatrically bohemian, a reaction to a reaction. Head-wrapped chicks waved incense sticks, young dreadlocked guys held their crotches and plotted and leaned. The JazzyFatNastees played often, but folks like Bilal, Mos Def, Erykah Badu or Alicia Keys often dropped in when they were in town, and when the Roots weren’t touring they came through. They played that night. Watching them live, it often seems like they are having the most fun in the room: Sweaty boy-men laughing at one another’s licks and riffs and jesting each other into a greatness that only they can comprehend.

It is difficult to untangle the biography of The Roots from the ghosts that swarm their city, Philadelphia. Philadelphia, only 90 or so miles south of New York, has long squatted in its shadow. It bears the visible scars of having endured decades of poverty, the consequence of white flight and shuttered industries and shipyards. As any Philadelphian will tell you, violence has shaped its landscape as much as its ability to hothouse musical culture, and the lives of Tariq Trotter, or Black Thought, the lead emcee of the Roots, and Ahmir Khalib Thompson, the bandleader and drummer known as ?uestlove, are illustrative of that.

Thompson was born in 1971 to Jackie Thompson and Lee Andrews. Andrews achieved fame in the '50s as the lead singer of the popular doo-wop group Lee Andrews and The Hearts. Trotter remembers that Thompson’s parents "kept gates on windows and a gate on the front door that was locked by a padlock.

"And if we couldn’t find a key to the padlock, we’d just be locked up in the crib," he told me. "So he was never in the streets because they sheltered him from that. His whole life he has been a musician, like his father."

Later, on the night before undun was set for release, told me that his father’s career was both "a blueprint" and a "cautionary tale." He was raised in the family business. At age seven he became his father’s de facto tour manager.

"I could navigate. I was the Human G.P.S. It was my job to find out the address of wherever the gig was and navigate us there. I would literally have Rand McNally maps as gifts for Christmas," he told me, laughing, on the night before undun was set for release.

I drove with him from NBC Studios, where The Roots had just wrapped "Late Night With Jimmy Fallon" (they're the house band for the late-night talk show), to his gig at The Blue Note. I was exhausted and all I’d done was hang around and watch his day, one that included four interviews, a photo shoot, hours spent rehearsing for that night’s show, an interlude in his drum room to learn a Max Roach solo he wanted to crib for the Blue Note shows, where he played two sets back-to-back. A passing handshake with Snoop in the "30 Rock" hallways had resulted in his playing the photographer for people who wanted a picture with the tall, seriously fragrant D-O-double-G. When we finally exited the building, he'd gotten a phone call from D’Angelo, the elusive soul singer for whom Thompson has acted as an anchor and an executive producer. We haphazardly crossed the street as fans stopped to shout Thompson out, and he spoke to each one without ending his phone call with D’Angelo, who wanted to make plans to meet for a brainstorming session after the Blue Note gig. Thompson, the entire time, was measured, never expending any more than the exact right amount of energy, and even as the night progressed he never once seemed tired.

Talking about the good old days, he told me, is something he truly enjoys. In so many ways, what he calls a childhood many others would see as gulag-like. After he mastered those navigational skills, he became his father’s wardrobe hand.

"I learned how to shine his shoes, whisk-broom his suits; he wouldn’t let me iron them though or steam them," Thompson said. "It was my job to choose the handkerchiefs; I learned how to clean suede, how to clean leather. I got his rings and laid out all of his jewelry.

"The [other] thing I had to learn was about was about staging. He’d teach me for about two weeks and then, on my own, I’d know to go to the club and mark the floor where the microphones go. Then I’d have to cut the lights; I knew not to use purple or green, that’s not good on brown skin, use peach. So I became his lighting director. Then one night his drummer Herman didn’t make the gig, and with a casualness he said, 'You know the gig, you play the show.' So my very first gig was at Radio City Music Hall."

After that concert Thompson would become the bandleader of his father’s show. He was 13.

It was around this time that Thompson met Trotter. There are certain people who have had lives so hard it is a wonder they are still standing. That is Tariq Trotter’s story. Both of his parents were higher-ups in The Black Mafia, a Nation of Islam–bred organized-crime syndicate based in South Philadelphia and Germantown. By 1974, the outfit controlled much of the city’s heroin trade, in addition to be being responsible for countless robberies and arsons and at least 40 murders, all while overwhelming and evading local authorities. The Philadelphia Inquirer said of them: "The Black Mafia is real. It is not a cop fantasy, newspaperman's pipe dream or movie myth. It is a black crime syndicate that has been growing unchecked in Philadelphia for the past five years. It has expanded and evolved into a powerful crime cartel with chains of command, enforcers, soldiers, financiers, regular business meetings and assigned territories. It specializes in narcotics, extortion and murder, with minor interests in loan sharking, numbers and prostitution. It has a war chest that bankrolls drugs and gambling and buys the best lawyers."

Trotter only recalls snatches of a childhood full of black dandies in floor-length mink coats, basement parties where basketball stars and celebrities mingled with the local gangsters, and of course, death. Both of his parents lost their lives to violence, ending his boyhood and sending him, like so many young men from his neighborhood, into his grandmother’s home.

A close friend of his told me: "As criminal as his family was, they used their activities as a means to an end. Tariq was always sent to the best schools because they definitely wanted something better—that was just the only way to get it."

Coming from such divergent backgrounds, high school would be the common ground for Thompson and Trotter: Philadelphia’s High School for the Creative and Performing Arts. Thompson was a jazz drummer and Trotter was studying Visual Arts. Thompson noticed that Trotter could rhyme and was ferociously witty and Trotter noticed that Thompson had an encyclopedic musical memory, and that he had gotten a toy sampler for Christmas.

"[Tariq] was like, 'You, come here. Play a break. Play a break,'" Thompson remembers. "So now I have to run to the basement, [down] eight flights of stairs and within three seconds play a drum break on my set and then program that into my sampler and then run back up eight flights of stairs, and when I would get there, he’s like, 'Yo never mind. I want to do "Top Billin."' Running back and forth was my existence with him every day."

After graduation the two found themselves aimless. On the way home from a Juilliard audition Thompson was mistaken for a famous bucket drummer from commercials and music videos. He’d never heard of the fellow, and quickly forgot about it. The following Saturday, while watching Soul Train, he and Trotter saw the Spike Lee-directed commercial with the drummer.

"We just looked at each other like,' Yo, why don’t we take a bucket and then go on the streets and do the same shit?'" Thompson said. "And just like that, Tariq ran to his grandmother’s house, I snuck in my mom’s kitchen, stole pots and pans and buckets and put them in a duffle bag, he met me at South Street at 6 o’clock, and the Roots were born, as you know it, the second week of June of 1992."

By the late '90s the Roots had been adopted by the neo-soul genre as its sonic helmsmen. They were the band that could (and did) play behind everyone. But being tied to a single sound made the band, and especially Trotter, who is far less musically sentimental than Thompson, uncomfortable.

"I just felt like we had to establish a range," Trotter told me. "Like I’ve seen people who insisted on saying things about themselves, like, 'We are only about acid jazz, man.' And I look at them, like, fucking acid jazz? What kind of longevity has acid jazz had? Seems to me, if you want to be around and transcend shit, it might be better to be known as just being masterful rather than being any one particular thing."

When neo-soul started trending down and hip-hop seemed to abandon the notion of the underground vs. the commercial, The Roots, who had staked their career on their otherness and their instruments, and on never doing what others did (like rapping about jewelry, drugs, or bashing the opposite sex), struggled to find their footing.

"Rich has a lot of regrets about The Tipping Point," Thompson told me in his drum room at the Fallon show. It is the size of a small walk-in closet. He apologized repeatedly for making me sit in what he calls his "hoard." Indeed, it is crammed with papers, records, and suitcases that threaten to engulf the drum kit. On the wall there are certificates that document his African ancestry (the Fula people); a small mounted flat-screen that plays an endless stream of old "Soul Train" episodes; and above the screen a picture of Thompson with Obama, the two smiling handsomely. Every now and again, his phone, which sat on the snare, buzzed. He would pause to check it.

"I’m waiting on reviews to come in", he told me sheepishly. "I’m like an expectant father."

His eyes traveled from the TV screen, where a young Rebbie Jackson was talking to Don Cornelius, back to his phone. This behavior, he said, is the result of The Tipping Point, the album the Roots released in 2004. It’s an uneven album, and besides the track "Star/Pointro" it can feel half-baked and scattered, even though it earned a few Grammy nominations.

"I think Rich literally told me it would take four albums to get our perceived glory back," Thompson said. "After that, there was a lot that past-tense talk about us."

It was at this point that each of their subsequent albums became stabs against the specter of irrelevance. The opportunity to join Fallon’s show in 2009 came at just the right time, as record sales declined and the major labels started to feel the bulk of their size weighing them down.

But there were concerns: Would they be seen as sell-outs? How would it work? What would the fans think? Would they be made fools of? Would they resemble the Porch Monkeys they had played in Spike Lee's Bamboozled? Could they be taken seriously playing a comedy show?

When they accepted, they found themselves for the first time in 20 years with day jobs, and no longer living out of suitcases. It was a radical change for a group that had toured anywhere from 280 to 320 days out the year. They were forced to acknowledge that they had grown up.

"Hip-hop made the youth count and have a real voice," Thompson said proudly. "So hip-hop really celebrates youth." Then he shrugged. "Now the same people who were reveling in that youth, like a mud-bath, they’re now no longer the youth. They’re 40. So now we have become the perceived enemy, because we’re talking about cleaning the house and not smacking asses in the club."

How I Got Over was the band’s answer to the problem of getting older in hip-hop.

"[It] was about saying we were in a vulnerable place," Thompson said, "and it was us saying, We don’t know what to do. Literally. We’re turning 40 and we don’t know what were doing here. And that’s why all of the themes on it dealt with some Rubicon, fork-in-the-road issues. Like crying out to God, or even questioning God. There was such a vulnerability to the album it provided such a great stall tactic. We had to figure out what happened next, and that is how it was until we realized we could tell stories. And the difference between our stories and everyone else’s, is our albums could be soundtracks to movies that don’t exist."

And so, to a movie that still doesn’t exist, undun became the soundtrack that does.