Chicago's original hip-hop trendsetters The Cool Kids reunite

By Tiffany Walden

Chicago’s current rise to one of the most influential hip-hop cultures in the world wouldn’t have been possible without mid-2000s underground sensation The Cool Kids.

In 2007, before instant access to music via streaming on smartphones, a then 23-year-old Chuck Inglish and 20-year-old Sir Michael Rocks used MySpace and YouTube to make skinny jeans, retro raps, snapbacks, and black mags cool — blazing the trail for future generations of DIY and indie artists.

After trying their hands at solo careers, The Cool Kids are making a comeback before year’s end. Chicago’s leading hip-hop blog, Fake Shore Drive, and Red Bull Sound Select are hosting a reunion show on Dec. 14 with the retro duo at Thalia Hall in the Pilsen neighborhood.

It’s a homecoming of sorts for the FSD founder, Andrew Barber. He first met The Cool Kids at the start of their career in 2007.

“The start of Fake Shore Drive probably wouldn’t have happened without The Cool Kids,” Barber says. “I would go to The Cool Kids concerts and shows and there would be lines around the corner.”

At the time, only the big four — Kanye, Twista, Common, or Lupe Fiasco — were getting attention on local, national, and international stages. Though The Cool Kids were packing out shows, Barber says, they still weren’t getting the coverage they deserved in blogs and other digital media sites.

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Barber felt he had to capture The Cool Kids and their development into trendsetters. So, he started Fake Shore Drive.

“I know Kanye and Kid Cudi were arguing about who wore skinny jeans first or whatever, but definitely the first person I ever saw rocking skinny jeans was Mikey Rocks. He was doing the skinny jeans in, like, 2006,” Barber says. “Chicago, for a long time, had either been the Kanye/No I.D. family tree or the Twista, Westside, Do or Die-type street stuff. The Cool Kids were doing something completely different.”

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The guys’ style was so different that people labeled their dress effeminate at the time, Barber recalls. Sound familiar? Think about the current Young Thugs and Famous Dexes of the music world.

“When The Cool Kids first started doing it, it was a big statement. It was kind of a bold move,” Barber says.

In July, when Barber posted the flyer for The Cool Kids’ reunion show online, longtime fans immediately shared the news and their excitement to see Chuck Inglish and Sir Mikey Rocks back together again. According to Barber, The Cool Kids are legends in Chicago.

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“I think now more than ever the world is ready for them,” Barber says.

Tickets to the show are $3 with an RSVP on the Red Bull Sound Select website. Without an RSVP, tickets are $10. Entry is first come, first serve.