Classic Albums: 'Lupe Fiasco's The Cool'

Classic Albums: 'Lupe Fiasco's The Cool' by Lupe Fiasco

Published Fri, December 16, 2022 at 12:00 PM EST

My litmus test to determine the lasting endurance of an album is whether or not the shit bangs like the day it dropped.

Meaning—if it came out now, does it still go? Most music, most art in general, is ephemeral; here today, gone tomorrow. And maybe that is the intention of pop music and culture, to be disposable in an economy dependent on the creation of more. Perhaps that's part of the reason why classic, timeless material is so difficult to produce. It's contrarian to the ethos of industrialization.  

What is even more difficult in creating art that can the work muster enough chutzpah, enough strength and genius and wit to alter one's perspective or have such a profound impact that its wave causes a seismic shift in culture.

Lupe's Fiasco's debut studio album, Lupe Fiasco's Food & Liquor, announced to the world there was something about this verbose skateboarder with glasses from the Westside of Chicago that was familiar: a little Native Tongue, a little N.E.R.D, a Kanye comrade fusing so-called high and low art and fashion. But there was something too, about Lu, that was different. An imagination and abstraction of thought and imagery that was ethereal and otherworldly. ...Food & Liquor, in part because of the undeniable smash of "Kick, Push", and "Daydreamin" with Jill Scott, (that won a Grammy out the gate), set the expectations—and anticipation—high for his next project.

His second studio record Lupe Fiasco's The Cool was released just over a year later in December 2007; it debuted at #1 on Billboard's rap charts, eventually going platinum. Another giant success for his label, 1st & 15th, that he ran with his friend and mentor Charles "Chilly" Patton, a connector and longtime impresario in Chicago house and Hip-Hop. While recording The Cool, Chilly was sentenced to 44 years in prison on heroine charges. Lupe's father passed away during this time, as did his friend, Stack Bundles. The youthful exuberance on Food & Liquor, on previous mixtapes, on "Touch the Sky," was not present for most of the record, understandably so, leaving the artist to mature quickly, grappling with ghosts and newfound fame and fortune.

The Cool, in comparison to ...Food & Liquor, is more sophisticated, contemplative, and darker, particularly the second half of the record. But that is not to say it does not have bangers. Out the gate, Fiasco switches into high speed double time, paying homage to fellow Westside legends Crucial Conflict, with an energetic ode to his hometown on "Go Go Gadget Flow". The song is undeniably fun, something Hip-Hop sometimes forgets, and puts on for the entire Midwest, in the playful chorus, impossible not to karaoke to.

"Go Go Gadget" is more than a prideful anthem for the city and "fly over" states, who were poised at this time to decenter rap's capital from the ATL and make a case that from Detroit to Chicago to St. Louis and Cleveland, the culture was alive and well. There is something in the fresh water that makes these emcees, well, fresh. And Lupe uses "Go Go Gadget," as a kind of Ars poetica, to let you know the shit he's on this album. At the top of verse three, he re-enters the driving bounce, produced by 1st & 15th staple Soundtrakk, with the couplet:

Like hey hey, I'm the boss/Rock Junya Watanabe Lacoste/Beyond clean, in phenom jeans, little rap Isaac Asimov..."

Apropos because Fiasco is indeed a futurist.


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An early adapter of Japanese style and fashion, he shouts out Comme des Garcons designer, Wantanabe, before most even knew what that house was up, too, (myself included), and well before they started putting hearts on Chuck Taylors. He also signals, comparing himself to the prolific science fiction writer Isaac Asimov, what we intimated on ...Food & Liquor, will be confirmed on The Cool, that Fiasco is reporting on the edge of a cosmopolitan world to come. Kwame Anthony Appiah writes in his book, Cosmopolitanism, an ethical and optimistic counter to colonial globalization, “I am urging that we should learn about people in other places, take an interest in their civilizations, their arguments, their errors, their achievements, not because that will bring us to agreement, but because it will help us get used to one another.”

The Cool finds Fiasco in transit encountering people from around the globe like on "Paris, Tokyo," when he gets an invitation to perform and grabs his Goyard trunk and has to leave his love but records for her in post-card vignettes the tails of his travels in what is one of the illest and sweetest love songs the culture has offered. Fiasco also wrestles with his newfound fame and the travails of being under the bright spotlights and big hit of the Matthew Santos-assisted "Superstar." Everything about Fiasco, seems measured, mindful. It is not without philosophic consideration that he examines the temporality of being "on" or even "cool." He yearns to be back home, "where the mood is mellow." Just 25 years old when The Cool comes out, Fiasco is seeing through the phoniness, like Holden Caufield, of the traditional mores of the dominant culture and rap culture and offering a new sensibility and approach. 

Most emcees stay in their braggadocio bag, and Fiasco can talk his shit with the best of them, but on "Hip-Hop Saved My Life," he departs from some of his more complex, esoteric bars and writes a stark short story, in the vein of Raymond Carver, inspired by Houston rapper Slim Thug. Thug did not know Fiasco had written about him until years later, but the song is a standout, worth revisiting for the portrait of an artist on the grind and verge of making it or at least making a go of it and the trials it entails. It continues to elucidate a point Fiasco is making about fame and art, that most people only see the top of the iceberg when there is a bedrock of sweat and sacrifice lurks beneath the surface.

Aesthetically, LUPE FIASCO'S THE COOL is in conversation with the avant—gard, not the mainstream of the culture.

His contemporaries are Pharrell Williams and Japanese designer Nigo. On The Cool, he is articulating and putting forth Hip-Hop's artistic idea and ideal of a new cosmopolitanism. Something that speaks to the influence the culture has had on the entirety of the planet. The Cool is something that is borderless, a highly curated ethos with a penchant and desire for beauty, reified. On what has become perhaps my favorite record on the album, "Gold Watch," Fiasco seems to be extending the ideas of Langston Hughes' poem, "Theme For English B," where a professor asks the class to go home and write a paper about themselves. Hughes responds with realist portrait of his walk home past the YMCA and admits to the reader of some his desires and interests:

"I like a pipe for a Christmas present. Or records—Bessie, bop, or Bach."

Fiasco's interpolation is much more extensive and expensive but speaks to each writer's yearning for beauty and cultivating spaces that inspire you. Fiasco's lists:

I like Yohji Yamamoto and a Max Roach solo/Leather Gucci belts and Guilty Brotherhood polos/I like Montblanc pens and Moleskine paper/I like Goyard bags and green Now & Laters."

And this is from 2007—before the blog era, before the internet was popping-popping; meaning Fiasco was in the streets and fashion houses and ateliers cultivating a style and knowledge that would influence a generation. Knowingly or unknowingly, A$AP Mob, and the rise of high/streetwear fashion, enters into Hip-Hop's lexicon and garment bag, because Fiasco in dialog with cutting edge visionaries who would go on to clothe the next and current wave of the culture. Fiasco extended the possibilities of how to be... well, cool.  And I can't see someone like Chicago designer Joe Freshgoods' IG post from somewhere in Japan and not think Fiasco had something to do with helping merge the east and the west for the betterment, and flyness, of us all.

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