Photo ©: The Private Collection of Dwamina Drew

Lupe Fiasco 'Story to Tell' Playlist

“Touch the Sky” by Kanye West Featuring Lupe Fiasco:

“Kick Push” was Lupe’s breakout as a solo artist, but his feature on Kanye West’s 2005 hit single “Touch the Sky” attracted international attention and shot Lupe to the moon. Truly a moment.

“Daydreamin’” by Lupe Fiasco Featuring Jill Scott:

Lupe snagged his first Grammy Award for “Daydreamin’,’’ featuring soul icon Jill Scott. In the lyrics, housing-project buildings turn into robots.

“The Coolest”:

In a single year, the Cool went from being the subject of one song to having an entire album named after him. On “The Cool” (2007), we get to know him and discover why, particularly on this track, he’s “the coolest.”

“Dumb It Down” by Lupe Fiasco Featuring GemStones:

When Lupe’s second album was ready for release, the powers that be asked him to “dumb down” his lyrics and content, thinking the material was going over the heads of casual fans. In response, he dropped “Dumb It Down,” poking fun at the requests, which he refused to address.

“Around My Way (Freedom Ain’t Free)”:

The first single from Lupe’s fourth album, “Food & Liquor 2: The Great American Rap Album Part 1,” samples a hip-hop classic by Pete Rock & CL Smooth. The sound might be a throwback, but the subject matter is modern. Lupe remains ahead of the curve.

“Pressure” by Lupe Fiasco Featuring Jay-Z:

Jay-Z served as the executive producer of Lupe’s “Food & Liquor” album, but the then-retired rapper also lent a hand with a guest verse on “Pressure” — a rare honor bestowed on a select few artists.

“Prisoner 1 & 2” by Lupe Fiasco Featuring Ayesha Jaco:

A song about prison ills, written from the perspective of a prisoner and prison guard. The deep, thought-provoking concept piece shows there are two sides to every coin.


You’ve heard that pizza-delivery drivers won’t go to certain neighborhoods, but do you really know why? Lupe takes a deeper look.

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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