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The Golden Age of Hip Hop (’86-’89)

This period in time gave birth to some of the most respected and talented artists existent today in the realm of Hip Hop (ex: KRS, RAKIM, SLICK RICK, PUBLIC ENEMY, EPMD, ULTRAMAGNETIC MCS, etc…).

Hip Hop had dispelled the myths of it being a short term passing and scenes throughout the world began to thrive. The main spot to scoop the latest wax was The Loop, Imports & Dr. Wax. There was a few Hip Hop club spots, but it was mainly house parties. Most likely the turntables were being worked by one or any combination of the following DJs; Plee Fresh, Boogie Boy, Jackboy, Adam 12, Pacman, Pumpin’ Pete, Rick The Ripper, & Gabriel Rican Rodriguez.

The Graf scene was at it’s heaviest point as writers started to further develop their styles and separate themselves from the writers in New York & L.A. The key new crews getting up were X-men, Ice Pack, Ice Inc., TCA, Def Crew, The Union, CGA, BTB, & SAS. From ‘85 till ‘87 it was all about the walls, tunnels & rooftops being hit. The stretch from Division to Logan Park was covered in Graf. Around ‘87 til ‘89 is when the trains became a focus. Trixster & the ABC crew made the Congress line the hottest line from ‘84 til ‘86.

The main spots doing regular Hip Hop events were The Rainbo & Jenals. The big tours that swept thru town were being booked at UIC Pavilion, The Rivera, & Aragon Ballroom.


J.P. Chill got his radio spot & begun planting the seeds of a legacy. On WHPK he created a forum that not only kept everyone current with the latest Hip Hop singles, but also gave a home-base for local talent to test market their latest creations. Mind you, JP Chill is currently still holding that same radio slot on WHPK 15 years later which to the best of my knowledge is quite possibly the longest running Hip Hop show in the country.

PLEE Fresh gets his show on WNUR 1986: Trixster & Deske have a brainstorm that leads to the forming of The Federation which is the combined forces of TCP, ABC, & MPC.

All Writers Meeting at Lincoln Park City Zoo

A spot over in Chinatown at 22nd & Cermak becomes known as the “Wall Of Fame” and is a homebase of sorts where writers from all over the city came to regularly put up new pieces.

The Spray Can Art book is released featuring a piece by Trixster from Logan Square making one of the first national known local Writers.

Graffiti ‘86 is a big gallery opening at the Axe Street Arena featuring most of the top Writers in the city.

The Chi-Rock nation was formed by a merging of two crews (Nine Trey Posse & TWR plus a few others) and developed into a enormous conglomerate that contained representation of all the elements of Hip Hop.

Chi Rock members OZ & the D.V.S crew release the first recognized Chicago based Hip Hop album that represented the city.

Sugar Ray Dinki-”Cabrini Green Rap” 12″

Richard Davenport a.k.a 3D of the Krazy Krew (MC, Breaker, & Graf writer), at age 14, gets a write up inRight On! magazine for winning a contest by doing two P.S.A’s for The National Safety Council.


Ramonski Love & Disco Dave starts the “Rapdown” show on WGCI.

PLEE Fresh introduces what is widely recognized as the first regular Hip Hop chill spot at a place named Steps up North by Loyola. It was like a boys/girls club that started at 3 p.m. in order to catch the younger crowd. There were DJS, MC battles, Graf writers showing off piece books, breakers on the floors & T.V. screens showing Style Wars or Wildstyle in the background. It lasted about 6 months, but when Plee went back to New York to stock up on music as he regularly did the person he left in charge let it fall apart.

In March Pinkhouse & Andrew Dunn kick off The RapHouse show on WKKC


Chicago Old Schooler, Cassius D, started and maintained a Chicago Chapter of the Universal Zulu Nation.

Kingdom Rock, Prodigy, Chain, & Riot split from their former crew, Empire Of Destruction, and establish The Ill State Assassins. Consisting of talent covering all areas of the Hip Hop spectrum and the know how of the hustle to get their projects completed and out to the public. Ill State continues on to be one of the most innovative, inspirational, and productive crews in Chicago.

Kingdom Rock of Ill State Assassins adds another notch to his belt as the promoter for the now famous parties at the Blue Gargoyle on the U of C campus.

His Majesti-”Armed & Dangerous” 12″. In ‘87 suburban N. Chicago MC legend,

Shakespeare, graduates High School and ventures out West to make this music thing happen. One year of struggling later he forms a new crew in the L.A. (W/Insane Poetry founder, Psycho) and becomes the first Chicago area MC to be signed to an established national Hip Hop label, Egyptian Empire. An album is completed, but the label goes out of business before it hits the streets.


Together A Posse-”Bring In The Funk b/w Don’t Bum Rush The Sound” (Feat D.J. Pumpin Pete) 12″

Whiteboy Mike-”Something To Dance To” 12″ (Jive)

Rhymepoets-Nation With A Nation EP

Upski became one of the first national voices for Hip Hop in Chicago with his “Reginal Rap Report” in the Source

Those who made use of the EL trains may have periodically looked around at one of the stops and saw an issue of “It’s Yours” (Elevated Press) taped up somewhere which was this short-lived, but classic magazines main and unique means of distribution. Another, Upski Innovation…

The popularity of Chicago’s Hip House sound, pioneered by guys like Fast Eddie & Kool Rock Steady, can no longer be ignored and nearly every rap album this year from New York to L.A. had one Hip House attempt on it.

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