A Conversation with The Cool Kids

A Conversation with The Cool Kids

Watch Andrew Barber’s seven-part conversation with the Cool Kids, which tells the stories behind the hip-hop pioneers’ origins, style, success and much more.

From Another Planet

3 Min Read

Legends. Pioneers. Trendsetters. Disruptors. The Cool Kids are known by these labels and more, and their influence only continues to grow. Having met in the mid-2000s via the early social media platform Myspace, the Chicago-based duo of Chuck Inglish and Mikey Rocks (now Sir Michael Rocks) bonded over a left-of-center approach to music production and formed a hip-hop group. 

After posting their initial creations on Myspace, Chuck and Mikey began making a name for themselves in Chicago’s nightlife scene — namely, at cutting-edge parties thrown by DJ duo Flosstradamus at the Town Hall Pub. The gatherings served as a launching pad for a new, Chicago-fueled sound spearheaded by artists such as Flosstradamus, Kid Sister, Million $ Mano (now Mano), Hollywood Holt (now HXLT) and others. Out-of-town DJs such as Diplo and A-trak made these events their first stop when visiting the city. Soon, tastemakers from coast to coast had the Cool Kids on their radar.

Such grassroots developments coincided with a music industry in free fall, and reeling from lost revenue due to MP3 piracy and file sharing. With record labels in desperation mode, groups like the Cool Kids took their music straight to music blogs instead of traditional outlets such as radio and BET or MTV. The Cool Kids weren’t trying to sell physical albums and CDs. Instead, they embraced the new digital frontier and largely gave their music away. 

The Cool Kids had another secret weapon: a unique fashion sense. Blending retro hip-hop looks from the ‘80s and early ‘90s, it stood out from the oversized, baggy apparel sported by most rappers. The duo’s skinny jeans, scarves, snapback hats and old-school sneakers proved to be game changers. Kids everywhere began to emulate the group’s style. And that style matched the Cool Kids’ sound, which meshed traditional boom bap with elements borrowed from the Neptunes and J Dilla. It all felt like it came from another planet. 

Once the Cool Kids’ breakthrough video for “Black Mags” impacted in 2007, hysteria reached a fever pitch. The duo became a hot commodity on the festival circuit and toured the world with the likes of M.I.A. and Lupe Fiasco. Chuck and Mikey pushed forward, releasing a slew of mixtapes and a critically acclaimed EP, “The Bake Sale” (2008). But drama with their indie label, Chocolate Industries, stopped the Cool Kids from officially releasing music for a number of years before they returned with an official debut album, “When Fish Ride Bicycles” (2011), via Mountain Dew’s Green Label Sound. 

Subsequently, Chuck and Mikey took a break to pursue solo albums and offshoot projects. During the Cool Kids’ hiatus, a new generation of artists (Tyler, the Creator and Chance the Rapper included) emerged and cited the duo as a major influence. Over the past decade, the Cool Kids have reunited several times, most notably for the album “Special Edition Grandmaster Deluxe” (2017) and on EPs with producers like Cardo Got Wings and the Alchemist. 

In 2021, the Cool Kids are returning with their most ambitious project to date: a triple album. Titled “Before Shit Got Weird,” it comprises a Chuck solo album, a Sir Michael solo set and a group effort. The undertaking comes as the Cool Kids are enjoying critical and commercial reassessment from multiple generations of fans. In our interview, we discuss that legacy as well as the duo’s journey and future.

Andrew Barber is the owner/creator of Fake Shore Drive, a Chicago-based media, management and events company founded in 2007. Andrew is also a playlist curator, published music journalist, artist manager, brand and record label consultant and media personality. Andrew currently sits as Governor of The Recording Academy’s Grammy board. His radio show, The Drive on Shade 45, airs weekly on SiriusXM, and has been on air for over six years. He has also hosted programming on MTV and one of Chicago’s top radio stations, 107.5 WGCI-FM. As a journalist, Andrew has been published in publications such as VICE, Complex, Fader, XXL, Mass Appeal and more. Andrew’s company, Fake Shore Drive, has been instrumental in the rise of Chicago’s hip-hop scene, having helped cultivate the careers of Chance the Rapper, Chief Keef, Lil Durk, Vic Mensa and the many other gold- and platinum-selling artists.

Andrew Barber is the owner/creator of Fake Shore Drive, a Chicago-based media, management and events company founded in 2007. Andrew is also a playlist curator, published music journalist, artist manager, brand and record label consultant and media personality. Andrew currently sits as Governor of The Recording Academy’s Grammy board. His radio show, The Drive on Shade 45, airs weekly on SiriusXM, and has been on air for over six years. He has also hosted programming on MTV and one of Chicago’s top radio stations, 107.5 WGCI-FM. As a journalist, Andrew has been published in publications such as VICE, Complex, Fader, XXL, Mass Appeal and more. Andrew’s company, Fake Shore Drive, has been instrumental in the rise of Chicago’s hip-hop scene, having helped cultivate the careers of Chance the Rapper, Chief Keef, Lil Durk, Vic Mensa and the many other gold- and platinum-selling artists.

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