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Deon Cole on Chicago’s First Hip‑Hop Wave and His Journey with Kanye West

by James Carter Senior News Editor

Deon Cole Reflects on Chicago’s Pioneering Hip-Hop Scene and Early Ties to kanye West

Published: January 26, 2026

the Raw Energy of Early Chicago Hip-Hop

comedian and Actor Deon Cole Recently Shared Insights Into The Vibrant, Yet undiscovered, chicago Hip-Hop landscape That Shaped His Early Life.

Cole Painted A Picture Of A Scene Brimming With Potential, Though Still Developing Its Distinct Voice.He Acknowledged that while Artists Were Not Yet Polished, The Energy And Creativity Were Unmistakable. “He Wasn’t Great Like That yet, But The Music Was Crazy,” Cole Remarked, Capturing The Untamed Spirit Of The Era.

This period, generally considered the mid-1990s to early 2000s, saw Chicago laying the groundwork for its eventual national recognition in the hip-hop world. Pioneers like Twista and Common were beginning to gain regional and national attention, but the scene remained largely underground. According to a 2023 report by the Recording Industry Association of America (RIAA), hip-hop/R&B remains the most consumed genre in the U.S., demonstrating the genre’s enduring cultural impact, a trajectory that began with scenes like the one Cole described.

A Budding Relationship With Kanye West

Cole Also Shared Reflections On His Early Relationship With Kanye West, Before West Achieved Global Superstardom. Their Paths Crossed During A Time When Both were Aspiring Artists Navigating The Competitive World Of Music.

While Cole Did Not Elaborate On Specific Details, He Implied A Sense Of Mutual Respect And Shared Ambition. This early connection provides a glimpse into the formative years of two artists who would eventually leave an indelible mark on the entertainment industry. Kanye West’s rise to prominence, beginning with “The college Dropout” in 2004, redefined the sound and aesthetics of hip-hop. Billboard Magazine recently revisited his discography, highlighting his constant innovation.

Chicago’s Hip-hop Evolution: A Comparative Look

Understanding the evolution of Chicago hip-hop requires acknowledging its distinct phases. The early era, as described by Cole, was characterized by grassroots movements and local talent. The drill music subgenre, which exploded in the early 2010s, brought national attention—and controversy—to the city. Today,chicago’s hip-hop scene is incredibly diverse,encompassing a wide range of styles and artists.

Era Characteristics Key artists
Early Era (1990s-Early 2000s) Underground,Raw Energy,Developing Sound Twista,Common,Crucial Knowledge
Drill Music Era (Early 2010s) Dark,Gritty Lyrics,National Attention Chief Keef,Lil Durk,King Louie
Modern Era (2016-Present) Diverse Styles,Mainstream Success,Experimental Sounds Chance the Rapper,G Herbo,Polo G

The Enduring Legacy

Deon Cole’s recollections serve as a reminder of the humble beginnings of both himself and Kanye West. They highlight the importance of local scenes in nurturing talent and shaping the broader cultural landscape.

The story underscores the power of early influences and the struggles faced by artists striving to break through. It also reinforces the notion that true artistry frequently enough emerges from environments of raw creativity and unbridled passion.

What are yoru favourite memories of the early Chicago hip-hop scene? Do you think the unique sound of Chicago continues to influence hip-hop today?

Share your thoughts in the comments below!

What was Deon Cole’s role in Chicago’s first hip‑hop wave, and how did his early collaboration with Kanye West influence his career?

Deon Cole on Chicago’s First Hip‑Hop Wave and His Journey with Kanye West

Deon Cole, the sharp-witted comedian and actor known for his work on Black-ish and Barbershop: The Next Cut, often speaks about his formative years in Chicago and his early connections to the city’s burgeoning hip-hop scene. His story isn’t just about comedic timing; it’s deeply intertwined with the rise of Chicago hip-hop and a especially notable relationship with a young Kanye West.

The Chicago Hip-Hop Landscape in the Early 2000s

Before Kanye west became a global superstar, Chicago’s hip-hop scene was a vibrant, yet largely underground, movement. Unlike the coastal dominance of New York and Los Angeles, Chicago developed a distinct sound – often characterized by innovative production, lyrical complexity, and a strong sense of community.

* Battle rap Culture: The early 2000s were heavily influenced by battle rap. Venues like The Regal Theater and various smaller clubs hosted intense lyrical showdowns, honing the skills of many future artists.

* Independent Labels: Labels like Rawkus Records had a presence, but much of the scene thrived on independent releases and mixtape circuits.

* Key Figures: Artists like Common, Twista, and Crucial Conflict had already established a foothold, paving the way for a new generation. Producers like No I.D.were instrumental in shaping the sound.

* The Influence of House Music: Chicago’s rich house music history subtly influenced the tempo and energy of its hip-hop, creating a unique sonic blend.

Deon Cole was immersed in this habitat, not as a rapper himself, but as a keen observer and active participant in the comedy scene that frequently enough intersected with hip-hop events. He frequented these venues, building relationships with artists and understanding the pulse of the city’s creative energy.

Early Encounters with Kanye west

Cole’s connection with Kanye West dates back to the early 2000s, before The College Dropout propelled West to fame. They met through mutual friends within the Chicago comedy and music circles.Cole has recounted numerous stories about West during this period, painting a picture of a relentlessly ambitious and incredibly talented artist still finding his footing.

* The Hustle: Cole often emphasizes West’s unwavering work ethic. even before his breakthrough, West was constantly producing, performing, and networking, relentlessly pursuing opportunities. He wasn’t just waiting for a record deal; he was creating his own opportunities.

* early performances: cole witnessed West performing at smaller venues, frequently enough struggling to gain traction. He recalls West’s frustration with being overlooked and underestimated.

* Production Prowess: Even in these early stages, West’s production skills were evident. Cole remembers being impressed by West’s ability to sample and create innovative beats.

* Shared Dreams: Both Cole and West were young artists with big aspirations, fueling a camaraderie and mutual respect.

Cole’s observations on West’s Rise

Deon Cole has provided insightful commentary on Kanye West’s ascent to superstardom. He’s spoken about the challenges West faced breaking into the mainstream and the evolution of his artistic vision.

* The “Dropout” Era: Cole remembers the excitement surrounding the release of The College Dropout. He notes how West’s unique style – blending soulful samples,introspective lyrics,and a distinct fashion sense – resonated with audiences.

* Navigating Fame: Cole has touched upon the pressures of fame and the impact it had on West. He’s acknowledged West’s struggles with public perception and mental health.

* Artistic Evolution: Cole has observed West’s willingness to experiment and push boundaries, even when it faced criticism. He recognizes West’s commitment to artistic integrity, even if it meant challenging conventional norms.

* The Chicago Influence: Cole consistently points to Chicago as a foundational element in West’s artistic identity. He believes the city’s creative spirit and independent mindset shaped West’s approach to music and fashion.

The Intersection of Comedy and Hip-Hop

deon Cole’s career trajectory highlights the symbiotic relationship between comedy and hip-hop. Both art forms often share similar themes – social commentary, storytelling, and a desire to challenge the status quo.

* Shared Audiences: The audiences for comedy and hip-hop often overlap, creating opportunities for cross-promotion and collaboration.

* Lyrical Storytelling & Stand-up: Both rappers and comedians rely on strong storytelling abilities to connect with their audiences.

* Social Commentary: Both art forms frequently address social and political issues, offering unique perspectives on contemporary life.

* Improvisation & Spontaneity: Both comedy and hip-hop value improvisation and the ability to react to the moment.

Cole’s Continued Success and Reflections

Today, Deon Cole is a triumphant comedian and actor, but he remains connected to his Chicago roots and his early experiences with Kanye West. He frequently incorporates anecdotes about his past into

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