Photo By: Michael T. Regan

In a large conference room populated by about 10 or so label representatives, Nichols hooked up his computer to drop some science on Tinseltown.

Nichols, a beefy guy with short dreads, knew that Iovine thought the recent Roots albums sounded old, and given how quickly rap trends change, Iovine was right. Yet Nichols was about to make an educated guess about which song would work in the room.

Iovine created his success in hip-hop with gangsta-funk tracks produced by Dr. Dre. On many of those hit records, Scott Storch had been a co-producer.

For those not familiar with the history of the Philly hip-hop band, Storch was The Roots' first keyboardist. While he's now best known for shepherding multimillion-sellers like Justin Timberlake's "Cry Me A River," and hooking up with Lil' Kim and Paris Hilton, he regularly produces tracks for his old bandmates, and Nichols had one on his hard drive.

One reason why the group Ahmir "?uestlove" Thompson and Tariq "Black Thought" Trotter founded at the High School for the Performing Arts in 1992 remains captivating is that the members yearn to be both experimental and popular, which is a near-impossible challenge in today's image-driven rap market.

The Roots' willingness to experiment with different genres and trends is what has kept them just above water for over a dozen years, but it has also alienated a lot of fans along the way.

So when frontman Trotter returned from a Storch-led session with the track "Don't Say Nuthin'," Nichols figured it sounded too much like Dre and Storch, not The Roots. But he also bet Iovine might like it.

At that time, The Roots needed a song, really just one song, that Iovine saw potential in. Their previous label imprint at MCA had folded and the band was just one of a handful of MCA artists whose contract had been absorbed by the Geffen division overseen by Iovine.

Drummer/bandleader Thompson likens the label transition to being first class passengers on a sinking ship one moment and stowaways on a five-star yacht the next. He says the vibe he got from the new A&R label reps was easy to summarize: "I heard about y'all. Fuck y'all. I'm not losing my job over you motherfuckers."

Photo By: Michael T. Regan

Nichols had no illusions that The Roots were about to be the next 50 Cent. But if Iovine liked the track, he might just give the band that push that could turn into their tipping point.

Trotter knew the meeting with Iovine was coming up when he wrote the lyrics to "Don't Say Nuthin'." In the last verse, he demands: "Give it here, Geffen Records, I'm off the handle, cut the check, and, yo, it better be as heavy as anvils."

Nichols cranked up the twitchy, percolating tune and waited for Iovine to react. The label head kept his feet up on the conference room's long, polished wooden table.

For at least half a minute, there was no reaction. Nichols began to sweat a little. No one else at the table moved, waiting for a sign from a mogul who can reportedly be mild-mannered one moment and pissy the next.

About 40 seconds in, Iovine's feet began to wiggle. Nichols turned around and saw everyone else at the table nodding their heads. Iovine had heard enough to decide "Don't Say Nuthin'" was going to be the first single from The Roots' new album, which would wind up being titled The Tipping Point.

Yet The Roots don't have an image to accompany the sound. Even though the band has backed up Jay-Z, Eminem and plenty of other top sellers, they've always been deemed a bunch of fringe, boho artists with artsy tastes.

When The Tipping Point came out, "the perception was, 'Oh I see. Y'all are trying to get paid now,'" Thompson recalls.

It didn't matter that other tracks on the album balanced commercial appeal and The Roots' legacy much more successfully. "Star" was heavily based on the chorus from Sly & the Family Stone's "Everybody Is A Star." The breezy soul-rap fusion could fit easily on a mix tape with tracks from the Black-Eyed Peas — not that Roots fans wanted to hear that.

When Nichols played "Star" in that conference room, Iovine asked who was singing on the sample (it had been a hit single for Sly Stone). He didn't see much potential in releasing that track as a single.

Photo By: Michael T. Regan

Not long after The Tipping Point hit stores, sales stalled at around 400,000 and the band had to reconsider its future. The album had sold fewer copies than the previous album (Phrenology), which had sold fewer than the one before it (Things Fall Apart). Where did The Roots fit into a black music marketplace dominated by slick Southern rap and glitzy R&B?

Will this experimental collage have commercial appeal? Even Nichols, upon inking the band's new deal with Def Jam label head Jay-Z, admitted his concern: "I told Jay, 'Dude, it might not sell shit.'"

When The Roots first signed with a major label, Geffen, in the mid-1990s, the band rode on the tail end of the bohemian rap trend. Later in the decade, the group got a nice bounce from its neo-soul connections, most notably with the single "You Got Me," which featured Erykah Badu on a chorus written by Jill Scott. For the album featuring that single, Things Fall Apart , The Roots had been shifted to MCA's black music division, which had a better understanding of how to promote the band.

"You Got Me" helped propel The Roots' best-selling album to date, Things Fall Apart, to near-platinum status (about 900,000 in sales). But the follow-up, Phrenology, while considered innovative by many critics, pissed off much of the core Roots audience because it mixed too many flavors into the boho melting pot, including rock, punk and electronica. It only moved around 700,000 copies. A solid showing, but a relative disappointment.

If the band members were going to fulfill their contract for Geffen, which meant releasing one more album on the label, they'd have to chase after that one special track again.

"I knew we weren't going to attempt a 'Don't Say Nuthin'' any time soon, so we sort of had the feeling that we would get deep-sixed if we turned in an art record," says Thompson about the origins of Game Theory . The group had already started kicking around ideas for new songs, and they weren't exactly the kind of material that would get SUV rims spinning.

The Roots crew asked for release from Iovine, and got it. The group, which has a reputation for blowing a lot of cash to experiment in the studio, convinced him that they would cost the label more money than they'd make from any moderately selling follow-up.

The search for a new label was enlightening and frustrating. Several execs were interested. Nichols impersonates one label rep in a "golly gee" tone of voice: "I remember when you played in my food hall in college. Now I'm a vice president. I'm really excited I can sign you guys." But the "creative bean counters" would temper the thrill by asking what to do with The Roots in a marketplace where image is everything.

Photo By: Michael T. Regan

Thompson, the public face of the band, is known for his voluminous Afro, eclectic tastes and occasional appearances on the Dave Chappelle Show, but not particularly for selling records.

There really isn't an obvious music-industry model for The Roots to follow. At first, a live hip-hop band was something of a novelty act. Even when the records were going gold, the members were making most of their money from touring.

They typically play over 200 nights a year. The records are sort of an ad for the shows, and the shows are a sort of an ad for the records, explains Nichols.

With the advent of file sharing, most records these days are selling less, and there's nothing anyone in the band can do about it. There's also a challenge for an aging band that has few peers making hits. In the past, there had been groups like Arrested Development, and later singers such as D'Angelo. Now, the most obvious counterparts topping the charts are Kanye West and Outkast.

Discuss the success of these acts with The Roots crew and they marvel about how West upped his profile when he nearly got killed in a car accident and then documented it in "Through the Wire."

"He says it: 'Almost dying was the best thing that ever happened to me,'" laughs Thompson. "I don't want it to come to that. Truly there has to be a better option than that."

As for Outkast, whose image takes inspiration from Funkadelic's freakout costumes, Nichols has joked about The Roots considering it.

"I was like, 'You guys better start fucking cross-dressing,'" remembers the manager. "You can't run out and get into a car accident. And you're not gonna be able to run around in a Rocafella chain and say you did 'H to the Izzo,'" he adds, referring to the Jay-Z tune.

Photo By: Michael T. Regan

Thompson considers dressing up or acting like a pimp all part of a modern-day minstrel act reminiscent of Bamboozled, Spike Lee's satire about the success of an Amos ' n' Andy-style TV show featuring The Roots as a house band called the Alabama Porch Monkeys. "Watching Bamboozled in 2000, I thought, 'OK, Spike, there's a little much. But life has become Bamboozled. I'm dancing with minstrels," says Thompson, referring to the rap world.

"We're not minstrel. We're not cartoony. We're not gangsta. We're not ambiguously sexual. We're not overtly sexual. We're none of those things." Thompson wonders if the images of white rock bands like Fall Out Boy are so carefully scrutinized.

And, unfortunately, that's a big problem in a pop culture world that doesn't afford enough time to explain a band that is more or less its own genre.

"I'm just real chill," says Trotter. "Sometimes I think I'm too laid-back, or I could be less laid-back for the benefit of the band, but it would be fake. I get excited sometimes, but it's natural and you can tell. I couldn't really do something contrived. It would come off as phony."

Much of Trotter's aesthetic comes from the artists he grew up listening to as a teenager, like KRS-One and Big Daddy Kane, who weren't the caricatures that fill rap music today, like Lil Jon and Young Joc. He tends to favor designer threads that are more preppy than ostentatious. Many of his raps follow a battle-and-boast style, in which he tells other rappers how fly his flow is.

Trotter rarely answers questions in more than a sentence or two, which you wouldn't expect from someone who's turned his passion for language into his livelihood.

And it's not as if Trotter has had an unremarkable life. Consider this: During the sessions for Game Theory, the group recorded a track titled "Pity the Child" in which the rapper discusses, for the first time, his parents' murders. When he was 1, his father was shot. Fourteen years later, his mother was stabbed.

Asked about how those events affected him, Trotter responds, "I'm sure it toughened my skin in some way, shape or form. ... I'm not really that self-analytical. But the way I am is probably because I went through so much shit."

Photo By: Michael T. Regan

According to Thompson, The Roots decided not to include "Pity the Child" because they didn't want to "pimp the tragedy." Nichols says it was because the group couldn't clear the sample on the track. Whatever the reason, "Pity the Child" won't get a proper release any time soon (but you can find a version on the latest Roots mixtape).

Another example: Trotter has two sons and a daughter. The sons both live in New Orleans with their mother and were there during Hurricane Katrina. The track "Bread and Butter" was his reaction to the tragedy (his sons and their mother are all safe) — but it also won't be on the album.

Still, many of the songs on the album illustrate how Trotter is becoming a more poignant lyricist.

In "Long Time," which is all about growing up in Philadelphia, he writes, "Shit, the ghetto might as well be the Gaza Strip/ You know all the monsters is/ Street walkers/ You don't see no consciousness."

Such a hands-off approach has also led many to wonder if Jay really cares about selling Roots records.

Byron Crawford, a writer for XXL magazine, considers The Roots a kind of credibility tax write-off for Def Jam (and has called Game Theory the worst Roots album ever).

Nichols won't go so far to say the signing was effectively a write-off, but he thinks Jay was interested in The Roots to make a positioning statement about putting acts he respects on his label. The reason he was interested in working with Def Jam was because Jay-Z saw the logic in a business model he proposed.

Realizing that The Roots were going to wither without a music scene to be a part of, he suggested incubating one around them. How?

Photo By: Michael T. Regan

Sign a slew of artists who have the same envelope-pushing mind-set as The Roots, pay a fraction of what you normally do for advances, and then market them on one Web site, with the understanding that the majority of the acts will only sell 5,000 to 10,000 records. If one happens to break out and sell hundreds of thousands of copies, great.

On the road, the band would take their Black Lily concept to a higher level. The Black Lily salons began in Ahmir's living room in the late '90s as a way to incubate new talent, allowing young, like-minded artists the opportunity to get on the mic.

Later, the shows moved to the Five Spot in Philly and the Wetlands in New York. Artists like Bilal and Kindred wound up getting signed as a result of the exposure.

The hope is to create similar salons in various cities and then have the more notable artists from these club nights tour from city to city.

Could it work? Possibly. But it would require a lot of money and attention from The Roots and Def Jam.

Nichols says Jay-Z was into the idea at the beginning, but there hasn't been much follow-up, and at the moment he's very concerned about the marketing and promotion setup for Game Theory.

"The setup for this album is pretty fucked up," says Nichols. "To be honest, it's the worst setup I've seen for any Roots record, bar none."

About 10 years ago, Thompson said he thought selling only 300,000 initial copies of Do You Want More?!!!??! was a slap in the face to the band. (The album eventually passed the 500,000 mark.)

About Game Theory, he admits, "Oh my god I would be happy if we do that — gold is like the new diamond in the industry."

"What I didn't know back then was the difference between talent and celebrity," says Thompson. "And now that I'm really immersed in this life I'm in, I clearly understand what it takes to make it. And I guess the decision factor is, are you willing to do what it takes to make it, or are you going to hang on to your principles?"

When The Roots took the stage at midnight, tracks like "Star" and "Don't Feel Right" were transformed into taut soul-funk with the accentuation of keyboardist Kamal's Rhodes piano, Leonard "Hub" Hubbard's virtuoso basswork and Frankie Knuckles' percussion. His bongo rhythms combined with Thompson's tom-toms to create percussive layers that leaned toward Afro-Latin jazz one moment and flittering electronica trills the next.

During an extended workout of "You Got Me," guitarist Capt. Kirk started a solo with spry, George Benson-esque jazz and ended it with Eddie Hazel-style space funk.

If Game Theory sells fewer copies than The Tipping Point, The Roots will go on. Unlike most rap acts, they actually carry the promise of a long life on the road, however arduous that life can be. They have improved with age. Trotter occasionally even engages the audience.

For most of the night, the Grassroots Movement organizers had been showing a reel of images related to the organization, including a portrait of Malcolm X in which the leader has his finger pointed to the side of his horn-rimmed glasses.

Every time I saw the shot I was reminded of something Rich Nichols said about the mugshot of Malcolm X that appeared on the cover of The Tipping Point. It was taken years before the activist became famous, at a point when no one could have guessed his potential.

"Would he go on to be Malcolm X? Or would he continue to do the pimping thing? And what the fuck would that mean at the end of the day? He gets fucking murdered... A tipping point could mean that this shit's about to blow up or catch on. What people forget is that there's also negative tipping points, and you can fall."

(n_gladstone@citypaper.net)