The Rich History of Chicago Rap Music

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The Rich History of Chicago Rap Music

The city of Chicago has a proud history of culture and music, but it’s easy to assume the golden age is in the past.

However, Chicago’s position as an influential cultural center is every bit as strong as it has been over the last century. Rap music is one of the most influential genres in popular music, and while connections to the Windy City may not be immediately obvious, they run much deeper than it appears at first glance.

To understand Chicago’s current position in the hip-hop industry, it might help to explain it this way: Chicago took a New York creation, flipped it upside down and created a unique, unmistakable version that sets them apart from the rest of the country. Let’s start our story back at the very beginning.

Sweet Home Chicago: The Home of Muddy Waters and House Music

The history of American popular music is in many ways the story of the growth and flourishing of African American culture. From the very beginning of radio and recorded music, African American music has been more profitable than any of its white counterparts, and the most successful white artists have benefited from the appropriation of African American music. Benny Goodman, Elvis Presley and Pat Boone are the most common examples of white musicians who gained massive popularity by playing black music — jazz, rock ‘n roll and soul, respectively.

The History of American Popular Music Is In Many Ways The Story of the Growth And Flourishing of African American Culture.

Jazz was first, and its natural derivatives followed. Next was the blues, and that’s where Chicago enters the story. Chess Records, started by the Chess brothers in Chicago, was the most successful record label in blues music, churning out hit after hit from artists like Chuck Berry, Etta James, Buddy Guy and Muddy Waters. In the 1950s and early 1960s, Chicago was synonymous with American popular music.

In the 1980s, Chicago was the birthplace of a highly-synthesized, rhythmically driven music that relied heavily on samples of classic soul and R&B tracks. This music assaulted the billboard charts and introduced the country to the new generation of artists from Chicago.

Chess records, started by the Chess brothers in Chicago, was the most successful record label in blues music, churning out hit after hit.

No, we aren’t talking about rap music. Rather, house music, a genre of electronic dance music, took over the music scene in Chicago — and later the whole nation. In every corner of the country, Chicago was recognized as the scene for house music. In many ways, the electronic dance music community is still mining the depths of house music and endlessly iterating on its tropes.

Chicago hip-hop artists would later use house tracks to create a sub-genre called hip house. Tyree Cooper and Fast Eddie get credit for this inventive mashup. Hip house did make some waves in New York City in the late 1980s, but ultimately it was a gimmick — a sub-genre flash-in-the-pan that would run its course before making an impact on hip hop as a whole.

The History of Hip Hop

Hip hop’s roots trace back even to the early days of disco. In 1974, Grandmaster Flash and Grandmaster Caz were spinning records at house parties in the Bronx. Afrika Bambaataa formed the Zulu Nation, which would influence every corner of the country as hip-hop culture began to mature in each individual city. Chicago, in particular, owes a lot to the Zulu Nation — which we’ll see in a little bit.

Hip Hop's Roots Trace Back Even To The Early Days Of Disco.

By 1977, hip-hop music had crossed the river and infiltrated all five boroughs. The common facets of hip-hop culture — music, breakdancing, graffiti art and DJing — had become a city-wide community. As these artists began to scratch and claw their way onto local radio, the reputation of hip-hop music began to reach beyond the five boroughs and out into cities around the country.

Kurtis Blow became the first rap artist to sign a record deal with a major label, and his anthem “The Breaks” would take the country by storm in 1980. The rest of the music industry began to take notice, and Blondie’s Debbie Harry would rap a verse in their hit single “Rapture.” The idea of rapping a verse wouldn’t raise an eyebrow today, but trust us — back then it was a huge deal.

The record industry in Los Angeles finally jumped on the bandwagon in 1981 and released the first West Coast Rap record, “Gigolo Rap” by Captain Rapp and Disco Daddy. Gangsta rap, which would be a driving force in rap music for the next three decades, came onto the scene in 1983 when Ice-T released an underground record in New York. The track, like his career, would stay underground for a few more years because mainstream radio wouldn’t touch it.

In 1984, Russell Simmons and Rick Rubin started the most influential of all hip-hop labels, Def Jam records, out of Rubin’s NYU dorm room. The first artist signed to the label was one LL Cool J. Back across the river in the Bronx, Kris Parker and Scott Stirling, better known by their stage names — KRS One and DJ Scott La Rock — started Boogie Down Productions, which would define New York hip hop for the rest of the decade.

Literal and overtly-metaphorical barriers were broken down when Aerosmith received a mid-career revival from their collaboration with Run DMC on “Walk This Way” in 1986. The popular narrative surrounding this track was that Aerosmith’s pop rock muscle helped lend credibility to this newfangled “rap” music. However, lost in this telling of the story is the fact that Aerosmith’s time at the top of the rock ‘n roll mountain had passed them by. It was the rap group’s popularity that propelled the rock group to greater heights, not the other way around. Hip-hop music had achieved legitimacy.

Gangsta rap began to dominate the rap industry as Public Enemy and N.W.A. blew up in 1987 and 1988. Balance in the industry was achieved when A Tribe Called Quest and De La Soul released decidedly non-gangsta records in 1989.

To this point in hip-hop history, all the action had taken place on the coasts — New York and LA. Chicago and other cities would eventually manage to organize their hip-hop communities and make enough noise to be noticed.

Gangsta Rap Began To Dominate The Rap Industry As Public Enemy And N.W.A. Blew Up In 1987 and 1988.

In 1993, Wu-Tang Clan released their first record. Snoop Doggy Dogg released “Doggystyle,” and Sean Combs created Bad Boy Records. The next year, OutKast released their first record, putting the Atlanta hip-hop music scene out into the national conversation. Suge Knight’s comments ignited the famous feud between East Coast and West Coast rap.

In 1997, Notorious B.I.G. was killed, and Life After Death became the biggest selling hip-hop album of all time. No Limit Records brought New Orleans gangsta rap on to the scene.

The next year, Big Pun from Puerto Rico and Slim Shady from Detroit arrived on the hip-hop scene. Korn and Limp Bizkit added rap to their rock and found tremendous commercial success, even if groups like 311 had been doing it for years.

In 1999, Lauryn Hill released her seminal album, still considered an all-time great. Additionally, Ludacris, Juvenile and Lil’ Wayne ushered in the rise of the Southern Hip Hop empire, joining Outkast as the next group of Atlanta-based hip-hop acts to make it big.

In 2000, Jurassic 5 dropped their debut album — Chali 2na, the most recognizable member of the group, hailed from Chicago. Nelly released his album and grabbed the spotlight for a moment, but this year undoubtedly belonged to Eminem, aka Slim Shady.

In 2003, 50 Cent arrived on the scene in New York. The Dirty South kept rolling out the hits, and Sean Paul introduced mainstream American audiences to Jamaican Dancehall.

Then in 2006, The Roots and Jurassic 5, though they’ve been in the game for a while, grabbed their moment in the sun to further illustrate hip hop’s growing diversity. Their success proved hip-hop music can be taken seriously not just for the lifestyle it portrays or the rhyming skills of the MC, but also for the quality of the music itself.

The Roots, a live band with an MC frontman, took hip-hop music in new directions. They proved that hip hop can be more than just an MC rapping over canned sample tracks from old soul records or sterile beats with bass that will shake the room apart.

Hip Hop Today

These days, hip hop has achieved full acceptance, so regional hip-hop scenes have largely, but not completely, vanished. Big-label, commercially-successful hip hop has transcended cities and gone worldwide.

The technologies that have been created by the explosion of the Internet have contributed immensely to the popularity and maturity of hip hop as an art form. Streaming music services, YouTube and music download sites have helped hip-hop music become the dominant force in popular music. Hip hop’s rhythms and musical concepts have proven to be a popular addition to every form of popular music. The syncopated bass that underpins most modern pop music is lifted straight out of hip hop.

The technologies that have been created by the explosion of the Internet have contributed immensely to the popularity and maturity of hip hop as an art form.

Because hip hop has reached commercial legitimacy, we have begun to see the emergence of some underground movements again, which have served to restore the unique regional character to the hip hop community. These sub-genres intermingle much more easily than they did in the 1980s and early 1990s, and the Internet has allowed these trailblazers to reach a wider audience without toiling for years in the underground clubs of their home cities.

So what has Chicago contributed to the rich history of hip-hop music? Just about as much as any other city outside of New York and Los Angeles can claim.

Chicago’s Hip-Hop History

House music may have dominated the national perception of Chicago’s music scene in the 1980s, but rappers were honing their craft at parties and underground clubs. The first hip-hop record produced in Chicago dates all the way back to 1980, when Casper released Groovy Ghost Show, a disco-heavy track that sounds exactly like what you would expect for a song recorded during that transitional period from one style of dance music to another.

The fist hip hop record produced in Chicago dates all the way back to 1980.

From 1986 to 1990, the hip-hop community gathered at the Blue Gargoyle on the South Side. Rap music was getting airplay on a few local radio stations, but hip hop was a live experience. Eventually, these parties would help the leaders of the rap community put pressure on music venues to feature local hip-hop artists, rather than bringing in out-of-town talent.

Still, Chicago’s rappers were having a hard time getting any respect on the national level. Chicago was the home of house music and a large, lucrative consumer market for the music industry. To break into the world of the major label music industry, a few members of the Chicago chapter of Afrika Bambaataa’s Zulu Nation saw the need for organization within the local hip-hop community. In response, Jitu the Jugganot and Lord Cashus D created a group called the New World Order.

The New World Order worked to convince venues to book local artists and radio stations to take local artists more seriously. When record labels began to kick the tires on the local talent, the New World Order served as a management structure to help promote and advocate for Chicago rappers. Dr. Groove, Source Magazine’s regional reporter for the Midwest, agreed to throw his support behind the Chicago rap scene as well. Thankfully, their hard work paid off. This cottage music industry helped a lucky few Chicago artists to break through, and they paved the way for every other artist who followed.

In 1991, rap group Ten Tray signed with Smash Polygram. Led by the aforementioned Jitu the Jugganot, they became the first Chicago rap act to sign to a major label. They put the first crack in the wall, which would be busted down by Common, Kanye West, Lupe Fiasco and others. Elsewhere, Kool Rock Steady would tour the world, serving as a hip-hop ambassador.

In 1992, a young Chicago rapper named Common Sense released his debut Can I Borrow a Dollar?, following in the footsteps of the more thoughtful rhymes of De La Soul. He would later shorten his stage name to Common.

Also in 1992, another Chicago rapper by the name of Tung Twista set the Guinness World Record for fastest rapper, spitting 598 syllables in 55 seconds. He also shortened his stage name to Twista. This would not be the last time we hear from him.

In 1994, Da Brat, from Joliet, Illinois, recorded Funkdafied. The record sold one million copies, making her the first female solo rapper to go platinum.

In 1997, Common and Twista released One Day It’ll All Make Sense and Adrenaline Rush, respectively.

In 2000, Common finally received his major label debut with “Like Water for Chocolate.” Another young man from Chicago by the name of Kanye West broke into the bigtime as a producer with Roc-a-Fella Records, collaborating with Jay-Z and his stable of artists.

In 2000 a young man from Chicago by the name of Kanye West broke into the bigtime as a producer with Roc-A-Fella records.

Two years later, in 2002, Common and Talib Kweli released albums proving that hip hop was still a powerful voice for socially-conscious expression.

In 2004, Kanye bet on himself, and his debut album “The College Dropout” went triple platinum. Twista’s “Kamikaze” was also a chart-topper that year.

A year later, Kanye’s 2nd album, Late Registration, hit, and he produced Common’s album, BE. The popularity of these two records helped to shift the focus away from gangsta rap and allowed hip-hop music to expand its reach.

In 2006, Lupe Fiasco came to the scene with his debut Food & Liquor, and Rhymefest debuted with Blue Collar. These releases, coupled with Kanye’s continued ascendance to the top of the hip-hop world, assured that 2006 was a good year in Chicago hip hop.

From 2007 forward, Kanye West conquered the world. His fingerprints are all over the modern hip-hop industry.

The next major development in the Chicago hip-hop scene would wait until 2012, when artists like Chief Keef, Lil Durk and Lil Reese would popularize a style of rap called Drill. Drill music is harsh, reflecting life in inner-city Chicago. Conversations surrounding Drill generally follow the template of a discussion about whether the violent nature of the music is actually contributing to violence in Chicago’s neighborhoods, so it is not without its share of controversy.

Musically, Drill has been described as a harder, more aggressive form of Trap, which was popularized by the Atlanta rap community a few years prior. Trap may belong to Atlanta, but Drill is uniquely and completely Chicago.

Drill music is harsh, reflecting life in Inner-City Chicago.

The Major Players

It would take an entire book to profile every important artist in the Chicago rap community, but that would very much be a book worth reading. Today, however, we will have to be content with a few of the most influential artists, starting back at the beginning:

Jitu the Jugganot

Jitu is quite literally a founding father of Chicago hip-hop music, having attended the earliest parties at the Blue Gargoyle. He helped create the New World Order, which organized and represented the artists in Chicago’s rap community. He was a member of Ten Tray, the first Chicago rap act to sign a deal with a major label.

He continues to be an influential leader in Chicago to this day. Without his hard work behind the mic and within the hip-hop community, Chicago rap music would not be the force it is today.

Da Brat

Born in Joliet and raised in Chicago, Shawntae Harris adopted the stage name Da Brat. After getting her big break in a contest sponsored by MTV’s Yo MTV Raps, she was signed by Jermaine Dupri.

In 1994, she became the first solo female rap artist with a platinum-selling album when Funkdafied sold over one million copies. Her success helped usher in a generation of female rap artists including Missy Elliott. As a guest artist, she was very much in demand, appearing as a guest on tracks with TLC, Brandy, Mariah Carey and Destiny’s Child. You couldn’t turn on your local Top 40 radio station in the late 1990s without hearing Da Brat.


A former world-record holder, Twista has outlasted so many other artists in the rap industry. After setting the Guinness World Record for fastest rapper in 1992, he kept working in the Chicago rap community, releasing Adrenaline Rush in 1997.

His 2004 album Kamikaze, debuted at the top spot on the Billboard Top 200 Album charts. His most recent album, Dark Horse, was released in 2014.

A Former World-record holder for the fastest rapper, Twista has outlasted so many other artist in the rap industry.


Raised in Chicago, Common was at the forefront of the more thoughtful alternative to dominant gangsta rap that arose in the 1990s. His tracks and lyrics offered a refreshing approach to rap music.

In Chicago, Common released his debut album, Can I Borrow a Dollar? in 1992. His follow-up album, Resurrection received widespread critical acclaim despite not getting major label support. Like Water for Chocolate, his fourth studio album, was arguably his breakout moment, and it has stood the test of time as a classic hip-hop album. His album Finding Forever reached number one on the Billboard charts in 2007, further bolstering his reputation as one of the most bankable rap artists in the industry.

Not content to express himself solely through music, Common branched out into a highly successful acting career. The youngest millennials may not even realize that Common was a musician first, which speaks to the depth of his talent as a multi-faceted artist.

Raised in Chicago, Common was at the forefront of the more thoughtful alternative to dominant gangsta rap that arose in the 1990s.

Lupe Fiasco

Lupe Fiasco was born the son of a chef and an engineer in Chicago. His first group, Da Pak, signed with Epic Records when he was 19 years old. They broke up before making any noise together, but he landed a solo deal after releasing several solo mixtapes. After appearing on Kanye West’s “Touch the Sky,” his debut solo album Food & Liquor received tremendous acclaim.

Lupe Fiasco followed in Common’s footsteps, using rap music as a vehicle for vivid and powerful storytelling and to address important issues. His follow-up album, The Cool, went platinum, sat at number one on the billboard rap charts for nine weeks and earned four Grammy nominations in 2009. Three albums since have cemented him as a superstar in the hip-hop galaxy.

Lupe Fiasco followed in Common's footsteps, using rap music as a vehicle for vivid and powerful storytelling and to address important issues.

Chance The Rapper

Chance the Rapper has released three incredibly successful mixtapes on his own, and he has refused every offer to sign with a major label. It is the most powerful example of the Chicago self-made work ethic we’ve seen to date. He has also chosen to remain in Chicago, rejecting the glitz and glamor of the two cities on the coasts. He is Chicago through and through.

Chance was born to a middle-class family on the South Side. His father was a part of the Chicago political scene, working for three famous Chicago politicians, including then-Senator Barack Obama. This relationship would come into play in 2016 when he was invited to the White House to work with President Obama and several other artists on the My Brother’s Keeper Challenge. Chance has also worked with his father on the #May23rd campaign to help curb gun violence in his home city. His social awareness and passion for activism are positively inspiring when you consider that he is merely 23 years old.

Musically, Acid Rap and Coloring Book have caught the attention of critics, industry tastemakers, and hip-hop fans alike. The rundown of “Top X” lists his recordings have appeared on is extensive. He has appeared at Bonnaroo and on many television shows that features live music.

In comparison to Kanye, who built a persona and a personal brand that has threatened to take over the entire world, Chance has climbed to the summit by being himself. He is a fan favorite, and his natural charms and activism win him favor every day.

Chance's refusal to sign with a major label is the most powerful example of the Chicago Self-Made Work Ethic We've seen to Date.

Kanye West

We’ve saved the biggest star for last. Kanye Omari West was born in Atlanta but raised in Chicago by his mother, Dr. Donda West. He was writing poetry at age five and showed an interest in music in the third grade. In seventh grade, he began creating beats.

At age 15, he inserted himself under the wing of No I.D., a legendary Chicago producer. This relationship would be a catalyst that would change the course of hip hop. No I.D. helped Kanye develop his signature musical style, sampling old-school soul records from groups like the Ohio Players. Kanye produced tracks for several Chicago artists, including Common. The opportunity to produce Jay-Z’s The Blueprint opened eyes across the industry, and soon his unique production style was highly in-demand.

Kanye’s production resume would have been enough to earn him a spot on his list, but he wasn’t content just being a producer. He was determined to make it big as a rapper, and the industry was soon going to learn you just can’t deny the unstoppable force that is Kanye West.

After a tremendous amount of hustle to get the major record labels to take him seriously as a rapper, the only offer he got was from Roc-a-Fella, for whom he was already working as a producer. They were looking for someone to step in and fill the void created by Jay-Z’s retirement, but they were reluctant to support West. Luckily for them, they struck gold.

West’s first album, College Dropout, was released in 2004 and took the country by storm. The signature Kanye sound, with old-school soul instrumentals sampled for the backing tracks and sped-up soul vocal tracks serving as the special sauce giving his tracks a distinctive character.

The lead single from the album was “Through the Wire,” which would stand for quite a long time as the most unorthodox introduction for an emcee. Following a late night recording session in LA, Kanye fell asleep behind the wheel of his car and nearly died in a car accident. His injuries required reconstructive facial surgery, and the doctors had to wire his jaw shut.

To deal with this adversity, Kanye did what all artists do — he worked it out with his art. He recorded “Through the Wire” while his jaw was still wired shut, and released it as the lead single on his debut album. The confidence Kanye displayed with this decision sums up his personality pretty well.

Late Registration and Graduation followed up The College Dropout, selling nearly nine million units combined, despite the fact that album sales across the entire industry were in free fall.

By the time Graduation faded from the limelight, Kanye’s style was heavily imitated on the hip-hop scene. Rather than establish his dominance, though, Kanye decided to leave it behind and do what he does best — innovate. His subsequent albums, 808s and Heartbreak, My Beautiful Dark Twisted Fantasy, Yeezus and 2016’s The Life of Pablo are all vastly different works that showcase a multi-faceted talent with few peers.

Musically, everything Kanye touches turns to gold. He has had the biggest impact of any single person on hip-hop music in the 21st Century. He is a sales juggernaut even as the industry is in constant flux, and he helped to break the mold for commercially-successful rappers. He wasn’t the first rapper to fall outside the gangster image, but he certainly broke down the wall and paved the way for the dozens of artists who have benefited since then.

Beyond the music industry, Kanye’s personality has taken over American popular culture in the last decade, as his career ambitions have extended beyond the realm of music. Fashion, business, technology and marketing are just a few of the different areas that have felt the impact of Kanye Omari West.

Polarizing, controversial and always interesting, Kanye is the current undisputed superstar of hip hop. No other artist can command the attention of the entire nation with a single tweet the way Kanye can.


Chicago’s Hip-Hop Legacy

By the time hip hop was born, the music industry in America had concentrated in New York and Los Angeles. Motown Records in Detroit, Stax Records in Memphis and certainly Chess Records right here in Chicago, all indispensable institutions in the world of African American music, had closed up shop by 1975. Motown moved to LA in 1972, which helps to prove our point, but their heyday had long since passed.

Hip hop’s origin story reads like the evolution of the urban landscape through the 1980s and 1990s. It grew from a misunderstood culture into an undeniable force that has touched every aspect of American art, weaving its way into the fabric of American society.

New York claims the title of the cradle of life for rap music, if not the other elements of hip-hop culture. When Grandmaster Flash and his contemporaries began DJing house parties in the Bronx in the mid-1970s, they were at the epicenter of the seismic events that would kick off earthquakes shaking the foundations of American music.

New York hip hop gained momentum in the 1980s and defined the genre in its first ten years. Then the West Coast rappers brought their own style onto the national scene, and the race was on. The battle of East Coast versus West Coast would dominate hip-hop music for twenty years until other parts of the country would finally break through and challenge for respect.

So why did hip hop start in these two cities? Were Chicago, Atlanta and New Orleans not joining in the movement? It all depends what you mean by “start.”

To those who were not participants in the hip-hop communities of our major cities, our first exposure to hip-hop music was through traditional music industry channels: radio airplay, album sales and MTV.

When A&R reps can take a subway ride in any direction and take their pick of the local talent, why would they bother to fly halfway across the country? Record companies didn’t know what to do with rap music at first, so their initial gambles were all placed on acts that were close to home. Starting in the 1990s, the hip-hop scenes in a few other cities managed to raise their profiles enough to compete with the titans. Atlanta had its moment in the sun and has earned its place next to the big boys.

So does this mean hip-hop culture didn’t flourish in the rest of the country the way it did in New York and Los Angeles in the 1980s? Of course not. Chicago’s hip-hop scene was every bit as vibrant as what was going on in the Bronx. Emcees, DJs, B-boys and graffiti artists were developing their own skills and styles here in Chicago, and they had to work twice as hard to earn the same respect on the national stage. And truthfully, they might be better off for it. In New York and LA, the record labels did all of that work for them, because they (eventually) saw the gold mine.

Going Their Own Way

In Chicago, it was all boot straps. Consequently, Chicago hip hop is a true meritocracy. In the commercial music machine, artists succeed and fail largely based on the amount of support they get from their record label. Because every artist in Chicago is self-made, only the best succeed.

Hip hop is, at its very core, the most socially-aware form of music we have ever created. Rock and folk musicians may have written the occasional protest song or shed the occasional light on social issues, but hip-hop music’s very raison d’etre is to shed light on the great urban issues of our time. When millions of people live in the close proximity of an urban environment, ideas can sprout that change the course of an entire nation. Once hip hop reached the mainstream, it changed the music industry forever.

Chicago’s homegrown talent has been a driving force in the current hip-hop community. You can’t have a discussion about today’s rap music without mentioning Kanye West, Chance the Rapper, Lupe Fiasco and even Common.

Hip Hop is, at its very core, the most socially-aware form of music we have ever created.

In fact, Chicago’s current influence brings up an interesting question. Did Chicago get the last laugh? Hip hop is past its adolescence, confidently swaggering through adulthood. The art form is fully realized, universally accepted and commercially successful. And of all the superstars, trailblazers and emperors who have presided over the growth of hip hop, who stands as the king of the hill in the end? Is it Jay-Z, Dr. Dre, Sean Combs, Snoop Dogg or Kanye? Our vote is Kanye.

In a way, Chicago hip hop benefitted from its geographical isolation. In New York, Los Angeles and even Atlanta, the pioneers became templates, with record labels searching for “the next ____”. True innovation is difficult in a commercialized environment where the familiar is celebrated.

The Chicago hip-hop community worked hard to earn the respect of the entire country, and without the external pressures of a record label dictating what “package” is going to sell, they did it on their own terms. Chicago artists created everything from the ground up — the community, the styles, the skills, the philosophy. There was no template in Chicago. Ten Tray, Common, Kanye, Lupe Fiasco — all of the iconic Chicago artists are true originals. Their styles are unique and unmistakable, and their influence is undeniable.

Chicago hip hop has no precursor, and it will never be replicated.

Listen to the complete list of artists and songs mentioned in this article