In April 2017, I sat down with Lil Bibby for a special Scoop B Radio Overtime session that shifted the focus from the “Drill” sounds dominating the headlines to the pure craftsmanship of Chicago rap. Bibby, often praised for his gravelly voice and mature-beyond-his-years perspective, took on the ultimate task: naming his Mount Rushmore of Chicago Lyricists.
Reflecting on this in 2025—now that Bibby has pivoted from a top-tier emcee to a mogul as the head of Grade A Productions (launching the career of Juice WRLD)—his 2017 picks offer a buttoned-up look at the DNA of Chicago’s lyrical heritage.
The Foundation: Common and Kanye
Bibby didn’t hesitate to start with the “Big Two.” While he represented the younger, grittier side of the city, he acknowledged that the path was paved by the soul-sampling and social consciousness of Common and Kanye West.
“You gotta have Common on there. He’s the one who really put that soulful, lyrical stamp on the city,”Bibby told me. “And Kanye… people talk about his production, but his early bars and the way he structured his verses changed the whole game for us.”
In 2025, these two remain the dual pillars of Chicago rap. Common provided the poetic blueprint, while Kanye provided the global scale. Bibby’s recognition of them shows his “student of the game” mentality—understanding that even the hardest Drill music is rooted in the lyricism that came before it.
The Speed and the Soul: Twista and Lupe Fiasco
To round out his four, Bibby looked toward the technical virtuosos. He named Twista, the undisputed king of the “double-time” flow, and Lupe Fiasco, arguably the most complex conceptual writer the city has ever produced.
“Twista is a legend, the way he manipulates the beat is something nobody else can do. And Lupe… Lupe is on a different level with the metaphors. He makes you think.”
By selecting Lupe and Twista, Bibby highlighted the technical diversity of Chicago. The city isn’t just one sound; it’s a spectrum of speed, soul, and storytelling.
The “Grade A” Transition
During our 2017 session, we also discussed Bibby’s own lyrical growth. He was moving away from the “Free Crack” mixtape era and starting to look at the industry from a bird’s-eye view. He realized that to have longevity, you had to respect the lyricists who lasted.
“I’m just trying to make music that sticks. You look at these guys on the Rushmore, they’ve been around for 10, 20 years. That’s the goal.”
2025 Retrospective: The Mogul’s Ear
Today, Lil Bibby is seen as one of the smartest minds in the industry. His 2017 Mount Rushmore reveals the “ear” for talent that allowed him to identify a superstar like Juice WRLD. He understood that while “vibes” are great for the club, “bars” are what build a Mount Rushmore.
| Lyricist | Specialty | Impact |
| Common | Soulful Storytelling | Defined the “Midwest” conscious sound. |
| Kanye West | Relatable Visionary | Merged high-fashion and street culture. |
| Twista | Technical Speed | Mastered the “Double-Time” delivery. |
| Lupe Fiasco | Conceptual Complexity | The gold standard for metaphors and world-building. |
Bibby’s 2017 session on Scoop B Radio was a bridge between generations. He paid his respects to the kings while preparing to build his own empire.
