A Conversation with Lupe Fiasco
Written By Andrew Barber
TV-MA
A Conversation with Lupe Fiasco
Lupe Fiasco

Watch Andrew's eight-part conversation with Lupe Fiasco, which uncovers the untold stories behind the rapper's rise to fame.

Log on to social media on any given day, and you’ll likely see Lupe Fiasco’s name cited in some kind of debate surrounding “who is the greatest hip-hop lyricist of all time?” Music lovers have pitted him against the likes of Kendrick Lamar, Andre 3000 (Outkast) and Black Thought (the Roots) — a very elite class. But after listening to Lupe’s work, even a casual listener will understand why he is held in such a high regard, and why conversations about his abilities often go viral. 

He has won a Grammy and has been nominated nearly a dozen times; scored numerous Gold and Platinum sales plaques; and charted multiple number-one albums and Top 10 Billboard singles. It all started in the late ‘90s on the west side of Chicago. After honing his craft alongside friends, the hip-hop-obsessed teenager had a chance encounter with a budding music executive named Charles “Chilly” Patton. The two became fast friends — and later, business partners — who set out to take the industry by storm.

When Lupe arrived on the scene in the early 2000s, releasing free or inexpensive mixtapes — not actual cassette tapes, but independently pressed (and sometimes homemade) CDs handed out at concert venues and on street corners, and sold at mom-and-pop record shops and flea markets — constituted the quickest (and cheapest) way for a rapper to create a local buzz and circulate music through the community. But Lupe’s music spread faster online than in the streets, an indicator of future trends. Coinciding with his successful mixtapes, Lupe became a message-board favorite, with pages and websites dedicated to deciphering his lyrics. Lupe soon landed a feature on Kanye West’s hit single “Touch the Sky.” A star was born. He became one of the most-anticipated young artists in the business. 

Lupe sees himself as having two careers: one as a mixtape artist, the other as a major-label star. At times, the paths have coexisted. But garnering and maintaining credibility in both spheres remains an incredibly difficult balancing act. Not every rapper can make the transition from great mixtape artist or battle rapper to commercially successful major-label artist. Most fail. Lupe has thrived in both spaces. 

How did he go from recording freestyles in his makeshift basement studio to hanging out at Jay-Z’s house? Lupe’s journey is anything but orthodox. It’s filled with broken promises, label problems and losing a business partner to a lengthy prison sentence. 

In this sit-down chat with Lupe, we discuss how he got his first record deal, his false starts with two record labels and his own 1st & 15th imprint under the Atlantic Records umbrella. The rapper also delves into the technology gaps he encountered early in his career, as well as the challenges of writing good raps as opposed to making label-approved songs. Lupe’s experiences in New York City with Jay-Z and the Roc-A-Fella Records crew, auditions alongside Kanye West, influential mixtapes and plans for a mixtape catalog are also explored. 

Andrew Barber is the owner/creator of Fake Shore Drive, a Chicago-based media, management and events company founded in 2007. Andrew is also a playlist curator, published music journalist, artist manager, brand and record label consultant and media personality. Andrew currently sits as Governor of The Recording Academy's Grammy board. His radio show, The Drive on Shade 45, airs weekly on SiriusXM, and has been on air for over six years. He has also hosted programming on MTV and one of Chicago's top radio stations, 107.5 WGCI-FM. As a journalist, Andrew has been published in publications such as VICE, Complex, Fader, XXL, Mass Appeal and more. Andrew's company, Fake Shore Drive, has been instrumental in the rise of Chicago's hip-hop scene, having helped cultivate the careers of Chance the Rapper, Chief Keef, Lil Durk, Vic Mensa and the many other gold- and platinum-selling artists.

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