The Cool Kids 'Story to Tell' Playlist

“Black Mags”:

The song that set it off for the Cool Kids, and their biggest hit to date. The track’s memorable video is often referenced as a starting point for the blog era of hip-hop. 

“Dapper Dan Leather”:

The latest release from the duo and first single from its upcoming triple album, “Before Shit Got Weird.”

“Mikey Rocks”:

Featuring an addictive hook (“I’m Mikey, I, I, I rock”) and rumbling production from Chuck Inglish, this solo shot from Sir Michael served as an entry point for some of the group’s earliest fans. 

“Gold and a Pager”:

The Cool Kids doubled down on their retro sound and look by introducing gold rope chains and beepers to a new generation who may have been too young to remember when both accessories were originally in vogue. 

The Cool Kids Featuring Jeremih, “9:15PM”:

A memorable slow-roller featuring the Cool Kids’ frequent Chi-Town collaborator, Jeremih. Sir Michael Rocks and Chuck handle rapping duties while Jeremih croons an addictive hook that makes the song feel like a Chicago stepper’s anthem.


The Cool Kids take it back to ‘88 on one of their early releases. Everything about this track is vintage and takes you to another era as soon as you press “play.”

“Connect Four”:

After a lengthy hiatus, the duo reemerged in 2017 with this bouncy tune which, despite its title, lets the world know it isn’t about the game.

The Cool Kids Featuring Ghostface Killah, “Penny Hardaway”:

The Cool Kids and Ghostface Killah? Yeah, that happened. When innovators and masters of their crafts collide, these are the results you can get. A slam dunk.

The Cool Kids Featuring Boldy James and the Alchemist, “WTF”:

A true family affair. The Cool Kids link with Boldy James to talk cash shit over an eerie soundscape provided by the Alchemist.

“Bundle Up”:

An icy anthem that has soundtracked the past 10 years of winter storms in the Midwest. Grab a jacket.


This is perhaps the first Bitcoin strip-club anthem…ever? They don’t call Chuck and Mikey pioneers for nothing.

“A Little Bit Cooler”:

When the Cool Kids emerged in the mid-aughts, they came in the game telling us just how cool they were. What separated them from the status quo? On “A Little Bit Cooler,” they break it down and provide receipts.

Boldy James and the Alchemist Featuring the Cool Kids and Shorty K, “Pots and Pans”:

If you’ve been following the Cool Kids, you know that Griselda standout, Boldy James, is Chuck’s first cousin. They’ve been collaborating for years, but their most recent effort is one of their absolute best. “Pots and Pans” landed on the deluxe version of Boldy James and the Alchemist’s stellar collaborative album, “The Price of Tea in China.” 

“Home Improvement”:

A Sir Michael Rocks solo shot from the Cool Kids’ upcoming triple album, this track sounds like it was created in another dimension.

The Cool Kids Featuring Ye Ali, “Driver”:

Chuck Inglish pulls up too clean with this smooth solo release from the group’s upcoming triple album. Ye Ali rides shotgun, providing buttery vocals.

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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