There are albums that define moments. In listening to these behemoths, our consciousness is changed. Time stands still within our sphere as these albums capture our given joys and struggles, and quickly crystallizes them in our mind. 

That’s why years later, when these albums play, each track conjures a specific nostalgia inside of us. They awaken us. They comfort us. They remind us of who we once were, and who we are today.

Lupe Fiasco’s The Cool hit during my transition into adulthood, from the streets of the West Side to being dropped in the middle of the North Shore. When “Gold Watch” and “Go Go Gadget Flow” come on, I think about my freshman year of college and some of the first friends I made during that time; those who embraced a nervous 18-year-old girl — me — coming off the grief of my grandmother’s passing while trying to navigate a foreign world. Sept. 25 marked the 14th anniversary of “Superstar,” the first single off Lupe’s sophomore album, and one of the songs my friends and I danced the night away to at a sorority ball.

The West Side hadn’t really had a rapper of our own to blow that big in hip-hop in a while. My generation grew up idolizing the dizzying tongue of Twista, the country twang of Crucial Conflict and the slick talk of Do or Die. We stuck our chests out with pride whenever their videos played on BET, MTV or The Box — because, like the South Side with Common, we had our own hometown heroes too. 

It felt good to see the West Side on the hip-hop map, which felt super dominated by the coasts at the time. However, their success felt distant to us. They were the big homies; so we were a little too young to feel part of their unique grind from the street to the TV screen.

Then came Lupe. Many of us first heard him on Kanye’s “Touch the Sky,” standing toe-to-toe with one of the biggest rappers of the time, who also happened to be Chicago bred. But when “Kick, Push” boomed out of my homeboy’s speakers for the first time in 2006, it sparked something new in us. We felt seen, not only because Lupe came out of the West Side like us, but also because he represented a new alternative brand of hip hop. 

Lupe wasn’t the flashy rapper with the dope boy swagger and chains and video vixens. He was a poet, still talking about the craziness we experience daily growing up on the underserved West Side, but unafraid to be Black and nerd out — a foreign concept to rap in the mid 2000s. His debut, Food & Liquor, which unbelievably just went gold this September, showed us that we could carve out spaces for our niches too. 

Last month, Lupe performed The Cool in its entirety on the Radical Stage at Riot Fest in Chicago on Sept. 17. Everything about his set took me back my freshman year in college.

Photo by Timoty Hiatt // Riot Fest

The dramatic weather of lightning and rain made for a perfect opening of The Cool, as the intro track “Baba Says Cool for Thought” began to play. This track — featuring spoken word by sister Ayesha Jaco who runs the local nonprofit West Side United — hit in a new way, given that Riot Fest is now located in the middle of an under-resourced North Lawndale neighborhood where the early signs of displacement and gentrification are already present. 

“They thought it was cool to tear down the projects and put up million dollar condos, gentrification… They think it’s cool to stand on the block hiding product in their socks to make quick dime bag dollars… They think it’s cool to ride down on you in blue and white unmarked cars busting you upside your head. Freeze. Cause the problem is, we think it’s cool too.”

Albums like The Cool are somewhat difficult to enjoy in a predominantly white crowd. It’s likely that the person standing beside you doesn’t feel the album the same way you feel it. As “Baba Says Cool for Thought” goes on, I wonder if the white women cheering next to me realize the role they’re playing in the lyrics right now. Shelling out $100 or more to attend a punk, rock and hip-hop festival in a neighborhood where at least 43% of the population are living in poverty. What role do I play too, I wonder?

“Free Chilly” plays next and it’s clear that Lupe is going to perform the album in order, track by track. This is one of those interludes that I’ve always wished were longer. Although it’s about Lupe’s friend being lost to the incarceration system, the track captures grief in a way that I related to, having lost my grandmother a year before The Cool dropped.

Photo by Anthony Nguyen // Riot Fest
Photo by Anthony Nguyen // Riot Fest

Together with his band, Lupe ran through “Go Go Gadget Flow,” “The Coolest,” “Paris, Tokyo,” “Hi Definition” and “Gold Watch” effortlessly. He didn’t miss a beat or a lyric, and the crowd didn’t either. Everyone rapped word-for-word back to him in unison, creating a magical moment under the night sky. And, bonus points — he opted out of singing the chorus of “The Coolest,” where he emphatically repeats “the coolest nigga, what.” 

In these festival crowds, many white people rap the N-word without any hesitation, and regardless of any Black person standing around them. The awareness of crowd and place on Lupe’s part made me rock with him even more.

“Everything you see right here is a part of my life and it could’ve been taken,” Lupe told the crowd. He then said “rest in peace” to everyone who has passed away, including rappers, trappers, gang bangers and surprisingly, police officers, before going into “Hip Hop Saved My Life.”

The thing about performing his album in order is, this particular crowd lost interest around this point in the show. The first half of The Cool is stacked with all the jams; radio singles and tracks that easily could’ve thrived on the radio at the time. The second half of The Cool are all album cuts; the songs that diehard fans listen to faithfully, without skips, when revisiting the album.

Chicago poet and author Raych Jackson, along with music artist Michael Penn II, a.k.a. CRASH PREZ, stood in the rain for Lupe’s performance. Both said watching him perform The Cool front to back took them back to 2006, which was a formative time for them musically. 

“I used to drive this 97 Honda Civic, y’all. When I tell you it was purple, and it was bootlegged as fuck, and we would blast The Cool. So when he did ‘Dumb it Down,’ we lost our shit. Rapped it word for word. It was on some super hometown hero shit,” Jackson said. “It felt really cool to rap The Cool with the people who knew the words.”

Chicago poet and author Raych Jackson, along with music artist Michael Penn II, a.k.a. CRASH PREZ, stood in the rain for Lupe’s performance. Photo by Tiffany Walden // The TRiiBE

Penn echoed everything Jackson said.

“He smoked that shit, 75-minutes straight,” Penn said. “He’s doing no backing, three-verse songs, damn near every song. Like, I’m usually not a fan of transitioning shit you make on the computer to a live band. I think that shit is really corny, but didn’t happen that way with [Lupe]. Very well executed.” 

Nearing the end of his show, Lupe reminisced about growing up not to far away from Douglass Park. 

“I used to live up the street. I got hit by a car when I was like eightyears old, and I went to that hospital right fucking there,” he said, pointing at Mount Sinai right on the corner of the festival grounds.

“I cried like a bitch before I came on stage,” he said, along with peace and love, before exiting the stage.

As the stage went dark, the crowd chanted “Lupe, Lupe, Lupe,” hoping for an encore of some of his hits that aren’t on The Cool; such as “Kick, Push,” “I Gotcha,” “Daydreamin,” his verse from “Touch the Sky” or even “The Show Goes On.”

“Thank you, Riot Fest, from the bottom of my heart,” Lupe said.

He didn’t come back out, though.

It never occurred to me that The Cool wouldn’t be a platinum album until people started conversing about it on social media after Riot Fest. I’ve always assumed it went platinum because it’s a classic. But it still hasn’t gone platinum today. After reliving the album, and the moment it created in hip-hop, there’s no reason it shouldn’t be platinum today.

is the editor-in-chief of The TRiiBE and a 2023-2024 John S. Knight Journalism Fellow.