Photo ©: The Private Collection of Dwamina Drew

Lupe Fiasco 'Story to Tell' Playlist

“Free Chilly (Intro)”:

A dedication to Lupe’s longtime business partner and friend, Charles “Chilly” Patton, who has been imprisoned since 2007.

“Kick, Push”:

Lupe’s breakout hit single and first release from his acclaimed debut, “Food & Liquor.” A song about skateboarding with deeper meaning. Play it anywhere in Chicago and the crowd will still lose it.

“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.


In our interview, Lupe cites “Mural” as his return to mixtape form on a major-label album. Accordingly, on “Tetsuo & Youth,” he does things he’d never tried before: Make music without traditional boundaries and major-label rules. This almost nine-minute showcase does exactly that.

“Streets on Fire”:

Lupe predicted the current state of the world on this song in 2007. The streets continue to be on fire in 2021.

“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 Cool”:

Lupe’s conceptual second album, “The Cool,” largely revolves around a character named The Cool. We first meet him on this choice cut from “Food & Liquor.”

“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.

“Adoration of the Magi”:

Many videos on YouTube are dedicated to deciphering Lupe’s lyrics. One connected to this track proves especially informative. What do the babies on the album covers of Nirvana’s “Nevermind,” Biggie’s “Ready to Die” and Nas’ “Illmatic” have in common? Listen to this song’s chorus and find out.

“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.

“Kick, Push II”:

The sequel to Lupe’s first hit, “Kick, Push,” features darker beats and rhymes than the original. As the yin to its predecessor’s yang, it’s a great way to close out the playlist.

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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