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The Best Midwest Rappers of All Time

The Midwest, often overlooked when it comes to its contributions to the hip-hop landscape, has produced some of the most influential and distinctive voices in the genre. Stretching from Chicago to Detroit to Ohio, the Midwestern region has proven time and again that it’s a hotbed for rap talent, birthing lyrical titans, trendsetters, and tastemakers.

Artists like Binary Star, with their lyrical prowess, or the emotional intensity of Chicago drill legend G Herbo, provide just a glimpse of what the region has to offer. Notable names like Frank n Dank and Do or Die bring with them the vibrancy of the club scene, while other talents such as Phat Kat and Chief Keef offer authenticity in their distinct ways. The politically charged discography of Brother Ali as well as the unyielding lyrical ability of Guilty Simpson, are mere hints of the richness of Midwest’s rap history.

So let’s get into it. From pioneers like Esham to underground rappers like Slug and Brother Ali to chart-topping legends like Kanye and Eminem, here are the top 50 greatest Midwest rappers of all time.

50. Murphy Lee

Essential listening: Murphy’s Law

Making a name for himself in the group St. Lunatics, it’s in Murphy’s solo work where the MC excels most. With a swaggering delivery and witty sense of humor, the Missouri native has the perfect mic presence to dominate the clubs, showing off his smooth ability on the underrated gem, Murphy’s Law.

49. Shawnna

Essential listening: Worth tha Weight

One of the best female rappers to hail from the Midwest, Shawnna is a monster on the mic whose quickfire delivery hits just as hard as her explosive choice in beats. Her fast flows and braggadocious delivery were carefully crafted for the clubs, making the most basic bar hit hard with limitless confidence in her mic presence. If only she had dropped more albums in her prime, the Illinois native might have ranked even higher.

48. The Cool Kids

Essential listening: When Fish Ride Bicycles

Chuck Inglish and Sir Michael Rocks have solid solo projects, but the MCs are never better than when they unite as the Cool Kids. Trading comical rhymes over ‘80s-inspired beats, the duo resurrected the rugged style of hip hop’s Golden Age on career-defining projects like The Bake Sale, sharing the mic with an infectious chemistry that makes any verse a delight.

47. Lil Reese

Essential listening: Supa Savage

Without an album to his name, Reese has thrived as a mixtape rapper since his come up in 2012. He’s got an ear for hypnotically catchy beats, gliding over punchy trap and drill instrumentals where Reese’s slick flow and hook-making talent shine. For over a decade, he’s represented the Chicago drill scene, always finding new ways to pen his grind in the streets over blaring Young Chop production.

46. Machine Gun Kelly

Essential listening: Lace Up

Hopping back and forth from punk to emo rap, Machine Gun Kelly has a natural versatility, so fans can never predict what the next project will sound like. His rugged delivery and impassioned singing add to the emotion of his lovestruck ballads, embodying the hard-hitting abrasiveness of punk while never losing his touch as an eclectic MC.

45. Trick Trick

Essential listening: The People vs.

With hit songs like “Welcome 2 Detroit” and “Detroit Vs. Everybody”, Trick Trick has turned his career into an expression of pride for his hometown. Rapping about all things from his passion for weed to his love for Detroit, he’s got the lyrical touch to keep up with the Midwest’s finest, but it’s in the MC’s delivery where he shines. With a ferocious, husky tone, Trick’s deep voice gives any verse an explosive impact.

44. Fredo Santana

Essential listening: Trappin Ain’t Dead

In the short time Fredo held the mic, he was a force to be reckoned with. The older cousin of Chief Keef, it’s clear that elite rapping runs in the family, as Fredo went bar for bar with countless legends from K-Dot to Kodak. His vicious lyrics were nothing new for Chicago, but Fredo’s seamless mix of hardcore verses and melodic hooks set him apart from the competition.

43. MC Breed

Essential listening: The New Breed

Back when hip hop was all East Coast and West Coast, MC Breed rose to give the Midwest a voice. From his gritty debut with DFC to the G-Funk glamor of The New Breed to the Southern club anthems of The Fharmacist, his career was a slideshow of different styles, and the MC pulled off each one. With limitless charisma and an arsenal of slick flows, he could master any sound.

42. T3 

Essential listening: Fan-Tas-Tic (Vol. 1)

Slum Village has seen a variety of personnel changes over the years, but T3 has always remained to keep the group’s legacy alive. His bars are witty and his flows silky smooth, levitating over Dilla’s funk-laced beats on classics like Fan-Tas-Tic, Vol. 2. Even today, T3 continues to impress, stealing the show from Larry June in 2023’s “Orange Village”. Whether he’s rapping with Baatin, Young RJ, or Elzhi, it’s a challenge for anyone to outrap T3.

41. King Von

Essential listening: What It Means to Be King

Hailing from Chicago’s O Block, King Von had all the in-your-face ferocity a drill rapper should have. He delivered every verse like it was his last, yelling into the mic over earthquaking, bass-heavy production that couldn’t match the fierceness of his delivery. Taken from the world too soon, his debut album Welcome to O’Block will always be an essential in the drill scene.

40. Stalley

Essential listening: Ohio

Dropping eight albums, eight mixtapes, and five EPs in a little over a decade, Stalley has quickly proven himself one of the Midwest’s most prolific talents. But despite his nonstop work ethic, the Ohio MC never puts quantity over quality – whether he’s spitting conscious rhymes over some soulful Apollo Brown beats or cooking up trap anthems with the Maybach Music Group clique, Stalley never stumbles in his pen game.

39. Chance the Rapper

Essential listening: Acid Rap

Although his debut album disappointed many, there’s no denying Chance’s talent in the mixtape scene. From 10 Day to Coloring Book, his blend of gospel cuts and soulful bangers have defined his style, rhyming at length about his faith over instrumentals that wouldn’t sound out of place in a church. Doubling as a talented singer, the Chicago MC’s music is as beautiful as the gospel ballads he’s inspired by. While his stock may be temporarily down right now, there’s no denying that Chance the Rapper is one of the best rappers to emerge from the Midwest.

38. King Louie

Essential listening: Drilluminati 

Even a gunshot to the head couldn’t stop King Louie from dropping music. Grinding in the studio since ’07, King L has become a pillar of the Chicago drill scene, blending his talent as a singer with his rage as an MC as he tears up countless bass-heavy instrumentals. From 2008’s Boss Shit all the way to 2022’s Life With Louie, King L may be underrated in the mainstream, but his consistency cannot be understated.

37. Vic Mensa

Essential listening: Innanetape

One of the most promising young Chicago rappers to emerge from the 2010s, Vic Mensa’s rap career hasn’t gone exactly the way fans thought it would. More than anything though, that speaks to his versatility, creativity, and endless desire to push against boundaries. When it comes to genre, Vic can’t be pinned down to one style. Whether he’s singing melodic rap ballads on The Autobiography, yelling his verses on the pop punk of 93PUNX, or gliding over the pop rap production of I TAPE, you can always count on Vic to bring an arsenal of quick flows and a limitless supply of introspective tales.

36. Big Sean

Essential listening: Dark Sky Paradise

Everybody knows Big Sean, but nobody gives him the respect he deserves. Since his breakthrough in 2010, the Detroit MC has only gotten sharper with each release, balancing a clever sense of wordplay with pop appeal to deliver projects as lyrically rich as they are commercially successful. Take a verse like his masterclass in flow on “Palisades, CA”, off the recent Larry June tape, The Great Escape, and it shouldn’t need explaining why Sean has stayed a mainstream staple for the past 10 years.

35. Lil Durk

Essential listening: 7220

Getting personal on projects like Almost Healed, Durk has the natural talent to blend introspective tales with hard-hitting production, never holding back as he spits emotional verses between addictive trap hooks. Gaining more acclaim with an elite run of features, his verses on the latest JID and Kanye albums have only made his skills more apparent.

34. Obie Trice

Essential listening: Cheers

Obie’s popularity may have peaked with 2003’s Cheers, but his lyrical prowess is still obvious twenty years on. The Detroit native is a natural storyteller, flexing his narrative talent on highlights like “The Setup” from his underrated debut. From Cheers to The Fifth, his knack for making hardcore bangers and slick storytelling ability have never changed.

33. Crucial Conflict

Essential listening: The Final Tic

Combining the funk of the West with the swagger of the South, Crucial Conflict forged a sound that will get any crowd moving. Full of heavy bass and screeching synths, projects like Good Side Bad Side were hand-crafted for the club, but it’s the group’s chemistry that makes them special. Passing the mic from member to member, Crucial Conflict work as a unit, hyping one another up and trading bars with an unrivaled level of charisma.

32. Kid Cudi

Essential listening: Man on the Moon: The End of Day

Is it any surprise that Kid Cudi made the list? His psychedelic take on rap music sounds as fresh today as it did when he debuted, mesmerizing every listener with his soothing voice and calm, whispery rhymes. Tackling topics of mental health most MCs wouldn’t ever discuss, his trippy brand of hip hop is as personal and raw as it is hypnotic. One of the most influential rappers of the past 10 years, Kid Cudi is absolutely one of the greatest Midwest rappers of all time.

31. Frank n Dank

Essential listening: The EP

Proof that lyrics aren’t everything, Frank n Dank never had the sharpest bars, but their club anthems were too catchy for anyone to notice. Chanting hooks about endless parties and getting high, the duo’s infectious energy will get anyone moving. From 48 Hours to The EP, Frank n Dank have rarely changed up their sound, but their limitless enthusiasm means the style never gets stale.

30. Copywrite

Essential listening: The Life and Times of Peter Nelson

If there was one word to describe Copywrite, it would be timeless. Whether you’re talking about his work in The Weathermen, his role in MHz Legacy, or his solo material, Copywrite has never missed the mark on a verse, spitting tight lyrical packages with a ferocious mic presence for twenty years straight. Full of intricate rhyme schemes and detailed stories of his life, the Ohio native has enough longevity to deliver quality bars for another forty years.

29. J Dilla

Essential listening: Donuts

Among the greatest producers to ever live, the legendary Jay Dee was no rookie with the microphone either. His rhyme schemes were as intricate as his beats, relying on his technical precision and braggadocious mic presence for his verses to hit hard. With the constant brags of Welcome 2 Detroit, Dilla’s swaggering talent as an MC was undeniable.

28. Da Brat

Essential listening: Funkdafied

Although she hasn’t dropped a project in decades, in Da Brat’s prime, she was a chart-topping force in the Midwest. Her flow is as slick as the funky beats she rhymes over, putting a poppy twist on the G-Funk sounds of the West Coast. Da Brat’s pen game is nothing extraordinary, but with her limitless charisma and endless supply of catchy hooks, she can make the simplest rhyme sound iconic.

27. Illa J

Essential listening: Yancey Boys

The younger brother of the great J Dilla, it’s no surprise that Illa J is a hip hop genius. Leaning more into R&B than the rest of his musical family, Illa switches between soulful ballads and funky rap cuts, turning albums like Yancey Boys and Home into genre-fusing experiments that would make his brother proud.

26. G Herbo

Essential listening: Swervo

Listen to PTSD and it shouldn’t need to be explained why G Herbo lands on the list. His deep, husky delivery is instantly recognisable, adding power to every bar and emotion to each vulnerable verse. With a taste for simple, high-energy trap production, it’s Herbo’s pen game that makes him special, never afraid to confess his deepest struggles as he cooks up tracks equally catchy and emotional.

25. Binary Star

Essential listening: Masters of the Universe

With an ear for dark, jazzy instrumentals, Binary Star’s music is as hard-hitting as it is underrated. On underground classics like Masters of the Universe, the duo shoot down all the wack MCs and sellouts, using their music like a protest to keep rap music raw and authentic. They may not be the most famous duo, but few groups in the Midwest have chemistry as tight as Senim Silla and One Be Lo.

24. Guilty Simpson

Essential listening: Ode to the Ghetto

While Black Milk brought the beats and Sean Price brought the energy, Guilty Simpson was the lyrical muscle of Random Axe. His clever sense of wordplay and knack for rhyme make him a monster with the pen, playing a major role in the masterful Random Axe, and dropping hidden gems through the 2010s like the jazzy Dice Game with Apollo Brown, where his slick delivery and precise lyricism shine through.

23. Eyedea

Essential listening: The Many Faces of Oliver Hart

Without much of a flashy delivery, Eyedea put all his effort into his lyrics, with each verse as intricately detailed as a ten page poem. He flexed his lyrical prowess on projects like By the Throat, thriving on the bizarre beats supplied by DJ Abilities. Outside the studio, Eyedea was even more of a lyrical menace – gaining a reputation as a battle rapper, few MCs in history could match his godlike talent as a freestyler.

22. Do or Die

Essential listening: Picture This

As funky as Compton but as sinister as Memphis, Do or Die picked elements from all over the rap world to craft a sound as catchy as it was threatening. Dedicating albums like Picture This and Headz Or Tailz to the street life, their lyrics are nothing new for the genre, but their buttery flows are too smooth to resist. Treating each track like an exercise in technical prowess, their chopper-style flows never fail to impress.

21. Phat Kat

Essential listening: Carte Blanche

One of Detroit’s most treasured MCs, Phat Kat is a lyrical menace who couldn’t deliver a bad verse if he tried. Full of clever wordplay and dense rhyme schemes, any verse from the Midwest MC would take a dozen listens to fully appreciate, never taking the easy route when it comes to rhyme. From the lyrical masterclass of Carte Blanche to the gritty deep cuts of Undeniable, few MCs can match the consistency of Phat Kat.

20. Chief Keef

Essential listening: Finally Rich

Dropping the classic Finally Rich when he was just 17 years old, Chief Keef certified his legend status from the moment he picked up the mic. Leading the drill scene to take over Chicago, the O-Block native is a relentless MC who strikes that perfect balance between melodic and hardcore rap. With the catchy hooks for a radio hit and the explosive bars to cause a riot, Sosa’s abrasive bangers appeal to all kinds of hip hop fans.

19. Noname

Essential listening: Room 25

The definition of quality over quantity, in just two albums, Noname has proven her worth as one of the best MCs to ever come out of Chicago. Her casual, spoken-word style delivery makes each verse sound like a conversation with the listener, spilling out all her deepest thoughts in carefully crafted rhymes and witty one-liners. Climbing album of the year lists with Telefone and Room 25, there’s no doubt that Noname will top lists again in 2023 with Sundial.

18. Nelly

Essential listening: Nellyville

A titan of the 2000s, hip hop wouldn’t be the same if not for Nelly. A pop-rap pioneer, he’s as great a singer as he is an MC, switching back and forth from soulful hooks to slickly-delivered bars, performing over instrumentals that wouldn’t sound out of place on an R&B album. From the iconic “Dilemma” to the summery sounds of “Ride Wit Me”, Nelly is a hit making machine whose music has aged perfectly.

17. Proof

Essential listening: I Miss the Hip Hop Shop

One of hip hop’s biggest what-ifs, Proof had all the right tools to become hip hop’s next superstar. His flow was smooth but his delivery was merciless, tearing up the mic with razor-sharp bars full of cold-hearted threats and clever one-liners. He stole the show countless times from his D12 partners-in-rhyme, showcasing the lyrical and technical prowess of a rap prodigy.

16. Brother Ali

Essential listening: Shadows on the Sun

Working two jobs as an MC and an activist, Brother Ali laces every bar with his beliefs, turning each project into a political statement against the corrupt and the oppressive. As dark as his subject matter can get, Ali’s music always sounds upbeat, with an ear for groovy instrumentals and a hyperactive delivery to keep every track vibrant and accessible.

15. Black Milk

Essential listening: If There’s a Hell Below

If you don’t know Black Milk, you don’t know Detroit. Whether he’s producing for Random Axe, thriving as a solo MC or featuring on others’ records, the rapper-producer has his fingerprints all over the hip hop landscape. When it comes to technical skill, Black Milk has no weakness – with an arsenal of slick flows, a poet’s rhyme skill and a singer’s voice, the Random Axe legend has no limits.

14. Esham

Essential listening: Judgement Day

Few MCs in the Midwest have left an impact like Esham. Debuting all the way back in ’89, he kickstarted the rise of Detroit in the hip hop landscape, dropping project after project all the way up to 2023’s Purgatory. A veteran storyteller, Esham’s vivid tales of death, drugs, and bloodshed practically birthed the Midwest horrorcore scene. His ferocious delivery and knack for brutal storytelling are still strong decades later, proving his status as a Detroit legend.

13. Boldy James

Essential listening: The Price of Tea in China

Boldy James stands tall as the best Detroit rapper currently in the game. Despite a slow start to his career, he’s surged ahead these recent, delivering album after album with unrelenting vigor. This laid-back MC, known for his killer flow and understated delivery, has an unparalleled work ethic, releasing eleven albums between 2020 and 2023, not to mention his extensive work from the previous decade. A musical chameleon, Boldy adapts effortlessly to any production style, his cold delivery and quick-witted bars establishing him as one of the most consistent MCs in hip hop today.

12. Tech N9ne

Essential listening: All 6’s and 7’s

The king of the chopper rap scene, Tech N9ne raps faster than lightning strikes. He moves his voice like it’s a part of the beat itself, spitting bars at superhuman speed without mumbling a single lyric. Chopper rappers tend to put style over substance, but Tech is the exception – always finding colorful new ways to hype up his talent, the Missouri native is a master of metaphors whose verses are as layered as his flows.

11. Slug

Essential listening: God Loves Ugly

What Slug lacks in an interesting past, he makes up for in his boundless creativity. He’s had no criminal lifestyle or traumatic upbringing, but thanks to his vibrant style as a lyricist, it hardly matters. Making up colorful personas and telling unpredictable tales of failed romance, the Atmosphere MC has the abstract storytelling talent and animated delivery to turn any concept into an instant standout.

10. Elzhi

Essential listening: Elmatic

With the all-round skills of a hip hop veteran but the recognition of an underground rookie, it’s no wonder they call Elzhi “Detroit’s best-kept secret.” After making a name for himself with the Nas tribute record, eLmatic, the Detroit MC was quick to beat the copycat allegations with projects like Lead Poison and Zhigeist, showcasing his unique talents as a rhyming machine and a technically gifted wordsmith.

9. Freddie Gibbs

Essential listening: Bandana 

Building one of the strongest catalogs in recent years, there is no denying the greatness of Freddie Gibbs. Taking the coke rap formula and putting a comedic twist on it, his tongue-in-cheek rhymes and witty sense of wordplay have defined his style on modern classics like Bandana and Piñata. But that’s not to say Freddie can’t get personal – diving into his deepest anxieties on $oul $old $eparately, Freddie Kane gets more versatile with each release, earning his title as an all-time great.

8. Twista

Essential listening: Kamikaze

Listen to Twista’s verse on Kanye’s “Slow Jamz”, and it shouldn’t need to be explained why he ranks so high. Living up to his name, every verse from the Chicago legend is a paragraph of tongue-twisters, spitting more syllables in a single minute than many rappers could in a whole song. From Runnin’ Off at da Mouth in ’92 to Shooter Ready in ’22, his tongue-twisting talent hasn’t faded in thirty years, never running out of steam.

7. Danny Brown

Essential listening: Atrocity Exhibition

You won’t hear Danny Brown on any radio stations, but for the abstract rap fans, he’s an icon. His pen game is just as bizarre as his rambling voice, full of over-the-top metaphors and unpredictable one-liners as grotesque and sexual as they are hilarious. But Danny isn’t all comedic rhymes like on Scaring the Hoes. On Atrocity Exhibition, his tales of addiction are brutally detailed, flowing over disjointed instrumentals only an MC as crazy as Danny Brown could master.

6. Bone Thugs-N-Harmony

Essential listening: E. 1999 Eternal

Although their West Coast inspirations are clear, the style of Bone Thugs can be compared to nobody – putting a dark twist on G-Funk, they reached their peak with E. 1999 Eternal, a landmark in gangsta rap full of infectious, melodic verses. Striking that perfect balance between hard-hitting street talk and head-bobbing pop appeal, the Ohio MCs crafted a sound no sane rap fan could dislike. Groups usually have weak links, but Bone Thugs are the exception, with each Bone having plenty of standout moments.

5. Royce da 5’9″

Essential listening: PRhyme

It’s an achievement to go bar for bar with Eminem even once, but Royce has been doing it his whole career. Whether he’s rivaling Slim Shady for the best verse on Hell: The Sequel, out rapping his peers in Slaughterhouse, or tearing up DJ Premier beats on PRhyme, da 5’9” has been a lyrical monster since the very start, building one of the strongest catalogs in the Midwest. His razor-sharp storytelling talent and superhuman ability to rhyme are near unbeatable.

4. Kanye West

Essential listening: The College Dropout

It’s not an opinion to call Kanye one of the best MCs in the Midwest; it’s a fact. Not only that, there’s an argument to be made that he’s the greatest hip hop artist of all time. Kanye’s clever sense of humor and showmanship on the microphone have led to some of the greatest albums in rap history, from the soulful highlights of The College Dropout to the constant flexing of Yeezus. Chipmunk soul, pop rap, gospel rap – Ye has tackled every style you could imagine, asserting himself as the most versatile rapper from the Midwest, and rarely missing the mark.

3. Common

Essential listening: Be

To pick out the best Common verse would be a waste of time, because there are simply too many standout performances to choose just one. What he lacks in an energetic delivery, the rapper makes up for in his lyrical prowess, sprinkling complex metaphors and genius storytelling into every project. With classics like Be and Like Water for Chocolate under his belt, Common Sense has the stacked catalog to prove why he belongs in the conscious hip hop pantheon.

2. Lupe Fiasco

Essential listening: Food & Liquor

A master wordsmith with an author’s creativity, there’s no question that Lupe Fiasco is one of the best rap storytellers to ever live. Narrating the resurrection of a murdered hustler on “The Cool” and turning his bars into a lyrical painting on “Mural”, Lupe could turn the most outlandish idea into a masterpiece of wordplay and rhyme. A godlike lyricist who never runs dry on ideas, each new release from Fiasco places him higher on the list of greatest rappers of all time.

1. Eminem

Essential listening: The Marshall Mathers LP

Even this long past his prime, no rapper in the Midwest has reached the level of Eminem. From a technical viewpoint, Slim Shady is a mastermind, with an infinite supply of flows and a variety of hyperactive deliveries to match his many personas. With classics like The Marshall Mathers LP and The Eminem Show, he earned his title as a GOAT contender years ago, yet he continues to drop lyrical bombshells today with new projects and an elite run of features. In every aspect, Marshall is the perfect MC, and one of the most well-rounded talents in rap history.

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