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By the summer after his senior year in high school, Wasalu Jaco had formed his own group, Da Pack, and had assumed his stage name of Lupe Fiasco. (He derived “Lupe” from the “lu” at the end of his real first name. “Fiasco” came from a song he liked called “Firm Fiasco,” by a group called The Firm.) Calvin Stark admits he wasn’t crazy about the pseudonym. “The Lupe part, I said, ‘OK.’ The Fiasco part, I said, ‘Do you really understand what fiasco means?’” Stark laughs. “[Fiasco] said, ‘I do, I do.’ But it was no use. I couldn’t talk him out of it.”
Newly dubbed, Lupe Fiasco began taking trips downtown to meet record-label representatives and eventually caught the eye of the Def Jam records producer Jay-Z. Bishop G had stopped rapping with Fiasco for a time, and he saw the growth in his friend when they got together later. “Damn!” he recalls telling Fiasco. “We all still good, but you sound like you adding some new shit. You been cheating?”
Fiasco was signed to Epic Records with Da Pack and later inked a solo deal with Arista Records. When Arista’s head, Antonio “L.A.” Reid, left in 2004, Fiasco was snapped up by Atlantic, his current label. Buzz began to build. He released a mixtape that included the song “Touch the Sky,” with Kanye West. In 2006 came Food & Liquor and stardom. This past January, he signed a footwear and apparel agreement with Reebok, and Food & Liquor was nominated for Grammy awards in three categories: as best rap album, best solo rap performance, and best rap song for “Kick, Push.” (Fiasco lost in all three categories.)
Since then, Fiasco has felt the dark stain of hip-hop culture-having his name connected to someone with serious legal troubles. In March of this year, a Cook County jury convicted Fiasco’s onetime partner, the hip-hop mogul Charles Patton, age 38, on drug charges. According to court documents, Patton had stored six kilos of heroin-worth about $1 million on the street-in a suburban storage locker. Fiasco was never implicated in the case, and prosecutors did not make any direct link between Patton’s drug dealing and the financial support he lent to 1st & 15th, Fiasco’s record label. (In May, Patton was sentenced to 44 years in prison.)
In talking to me, Fiasco would discuss Patton only in veiled terms, saying things such as “My partner’s legal situation,” or “My partner’s arrest.” Fiasco testified on Patton’s behalf during the trial, and, in a letter to the court, expressed support for his former partner, saying, “I love Charles . . . I am deeply saddened by his circumstances and will stand by him and his family no matter what occurs.”
He has also had to grieve the death of his father in February of complications from diabetes and heart failure. “My father was The Man,” Fiasco says. “He was a big influence in so many areas. That’s what keeps me from limiting myself, because he was such a Renaissance man. I’ve always wanted to be like my pops.”
And despite his thriving career, Fiasco has struggled to emerge from the long shadow cast by Chicago’s most famous rapper, Kanye West, though the two remain close and are teaming on the Child Rebel Soldier project. The irony, Fiasco says, is that his 1st & 15th label and his connections helped make West what he is. “He had his notoriety as a producer, but people didn’t know him yet as a rapper. His payback to us was: ‘Lupe, I’m blown up. Let me help you.’ He does a lot of stuff for me out there.”
Fiasco’s success has sometimes made it hard for him to stay true to his message. For a time, he succumbed to the bling stereotype, a façade that still calls to him at times. “I was actually sucked in quite willingly,” he recalls of the period shortly before the release of Food & Liquor. “And it’s because I thought at first that that’s what you needed to succeed. If I want to get my albums in the stores then I have to be like that, too. I had two chains, a diamond bracelet worth, like, $20,000. I had a $10,000 watch; I drove around in a BMW with 20-inch rims. I was there. I had it. I wanted it.”
He saw the rocks behind the siren’s song while sitting at home one day. “I was hungry, but I didn’t have any cash on me. And I was thinking, Here I am at home in this crazy little decked-out apartment, bejeweled and hungry. And it dawned on me: This is stupid. I’m getting out of here. The façade started to peel away.”
He says it helped to read Noam Chomsky, the M.I.T. linguist and political critic, particularly his writings on the mass media’s complicity in glamorizing the kinds of violence that have become the staple of rap videos. “A few things that he touched on reaffirmed completely what I was thinking,” Fiasco says.
Even so, he occasionally feels the pull of material trappings. “Even now, I still fall for the façade,” he says. “I just recognize it more quickly.”
* * *
The tour of Fiasco’s ‘hood is over. Fiasco swings the Range Rover to a sidewalk just off Ohio Street near Franklin. I had stopped asking questions long ago, realizing his stream-of-consciousness riffs led to their own exotic places. I feel brain weary, overwhelmed, the way a premed major might after a particularly demanding advanced chemistry class. But when I glance back, I see that Fiasco, looking as fresh as when he picked me up, is already working one of his cell phones, eyes flashing behind nerd glasses, music bumping, his mind, his day still revving, supercharged, intense as a starburst.
Photograph: Saverio Truglia