Photo by Samuel Walcott

The Cool Kids Return to a World They Created

Sir Mikey Rocks and Chuck Inglish inspired a generation of young rappers when they emerged a decade ago. Now, after years away, they're back with 'Special Edition Grand Master Deluxe.' They're still streets ahead.

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Oct 22 2017, 9:45am

Photo by Samuel Walcott

Back in 2006, when he was a loudmouthed skinny jeans-wearing teenager, Antoine Reed would often be harassed and, on occasion, even bloodied up by the local gang members in Matteson, the poverty-stricken, south-suburban Chicago neighborhood where he was raised. "Coming up it was a fight," the emcee better known as Sir Mikey Rocks, one half of the tastemaking Chicago hip-hop duo The Cool Kids, says looking back at the group's salad days. Back then, even as Chicago's art-school-educated Kanye West topped the pop charts, it was generally looked down upon to be rapping about the topics Rocks and his partner Evan "Chuck Inglish" Ingersoll preferred: bizarre, slightly nerdy ones like video games, fly haircuts, and Star Wars. "There was a lot of struggle and a lot of strife," Rocks says of The Cool Kids' come-up. "That shit wasn't all smiles and rainbows."

Rocks no longer has those sorts of concerns. That loose, goofy, self-empowering brand of hip-hop he and partner Inglish pioneered a decade ago—all 808s, minimal retro sonic and feel-good rhymes, dubbed at the time as "hipster hop"—is decidedly en vogue now. And their unorthodox decision back then to build a grassroots fanbase almost exclusively online? Now it's par for the course.

On a recent fall afternoon, however, Rocks has a different sort of problem to contend with. "Let's all just be cool," the rapper, wearing a coral pink jean jacket, white t-shirt and a Cleveland Indians baseball cap, says, suddenly tense. He momentarily takes a break from his lunch at a touristy seafood restaurant on Chicago's Navy Pier to survey the situation. There before him floats a bumblebee. And damn if the little dude isn't circling the rapper's crab cake sandwich right now. "Clap his ass!" Inglish, the more boisterous and wisecracking of the two musicians, dressed in all black, yells back at his longtime collaborator. He's unable to hide his palpable glee at his typically blasé partner's sudden uneasiness. "No, don't clap him!" Rocks snaps back. "He might spaz out. They smell fear. Let's just be cool."

"He's gone," Mikey says with relief as the bee departs. Inglish is still laughing.

"Nah, he just went to go get his boys."

Spend time with The Cool Kids and this sort of comedic interaction is bound to happen several times. It's such interplay between its members that always made the duo stand out. It's been a while though since anyone's seen it up close. Following the release of their long-delayed debut album, 2011's When Fish Ride Bicycles, the group has been more or less defunct. They worked on respective solo projects and even suggested the group was done for good. Even now, after reuniting and announcing a forthcoming album via Twitter before ever writing a single bar, and last month releasing a fierce, wildly experimental new album, Special Edition Grand Master Deluxe, they still don't spend all that much time together. That's because Inglish lives in LA while Rocks still resides in Chicago. But "now is probably the best we've ever been," Inglish, the over-the-top goofball to Rocks' introspective intellectual, says of the pair's personal and creative connection.

Their new album goes a long way towards justifying his sentiment. Special Edition is the most diverse offering yet from the Cool Kids. It's soulful (Syd-featuring "Simple Things"), slinky (Jeremih-featuring "9:15"), jazzy ("Jean Jacket") and gritty ("Break Your Legs"). As is to be expected, it's also highly lyrical. "Honestly I don't think anybody can outrap him," Inglish, who raps on the album, says of Rocks before noting that his bars have gotten quite heavy.

They'll admit they're breaking new sonic ground with Special Edition. That retro-rap tag The Cool Kids were long given? Don't feed them that anymore. "Ever since we met we've already had 10 different directions that we could go in and a bunch of different aesthetics musically that we could capture," Rocks says. This diverse new sound, he says, is simply a long-gestating reveal. "We've already tested all this out in the early years," he says of the experimental sonics on their new album. "You guys just hadn't heard it yet."

Sure, there's truth to the rapper's statement, but at its core the group's recipe for success hasn't really changed all that much. Dry humor, incisive wit and a sense of inclusiveness—it's what made The Cool Kids compelling from the jump and what remains enticing about them today.

"We've already proven what we can do and who we are," Rocks continues. "I just don't gotta fight for it anymore. I don't have to struggle for it. I don't have to look over my shoulder and be on the defense. I know what I'm doing now. I know who I am. I know what I'm aiming for."

Inglish agrees, but says he needs to clarify. The producer will admit it's nice to be back in The Cool Kids, but in some ways he always sensed they were ahead of their time. To that end, he doesn't see this current moment so much as a reunion but rather a new beginning. "I knew we were a little too early and I've strategically lived my life ever since," Inglish says. His motto in the intervening years? "Just don't fuck up."

The Cool Kids formed in 2005 after Rocks and Inglish exchanged messages on Myspace. Their story wasn't all that uncommon back then: a Chicago-raised rapper, Rocks, discovered a beat from a Detroit-raised producer, Inglish, and soon the two met up in person. They began working on music together almost immediately. In 2007, The Cool Kids released their first mixtape, Totally Flossed Out, via their newly minted Myspace page. DJ's including Diplo and A-Trak took notice, trying to woo them with deals to their respective Mad Decent and Fool's Gold labels. But the group instead signed to Chocolate Industries and released their breakout Bake Sale EP in 2008.

Thanks to the ever-growing presence of rap blogs, their spacey and breezy, retro-leaning sound, recalling Golden Era hip-hop artists like LL Cool J, made them internet famous seemingly overnight. It also didn't hurt that they released five follow-up mixtapes in the following years. "There were literally lines down the block to see them perform" in Chicago, Andrew Barber, founder of the city's influential hip-hop blog Fake Shore Drive and an early champion of the group, remembers. Barber credits The Cool Kids with bringing the Chicago hip-hop scene "into the digital age" and inspiring a young generation of hip-hop fans to be self-starters. Nico Segal was only in middle school around this time, but the Social Experiment member and co-founder of Kids These Days says he and his friends like Chance and Mensa took their cues from The Cool Kids. "They killed shows," Segal, who attended one of their early gigs at Millennium Park, recalls. "It was the talk of the town. Their live presence was really impactful and that resonated with us a lot."

Inglish doesn't deny that Chicago hip-hop artists like Segal, Chance, and Mensa may have been inspired by The Cool Kids. In fact, Chance recently told him as much at a local music festival. "Him, Vic, everybody that's cracking now, they can draw the line from us," he says. "But we've drawn our line from Lupe Fiasco. Without Lupe I don't know if we come together." More specifically, Inglish says, it was his and Rocks' discovering how Fiasco, "a black dude who wore glasses, had a song about skateboarding and was into anime films," could be successful in hip-hop that moved them to be unabashedly themselves with their music. "That gave us the gas to be like 'Damn, we can be us and maybe people can get off on that.'"

When The Cool Kids were first popping up flashy rap about guns, money and women was trendy. "There was no way you could just be a regular kid and rap," Inglish offers. But him and Rocks doubled down on a message of self-expression and individualism. "We came out and said 'Be yourself and do your own shit. Feel good about it. Be fresh and don't take shit from people, bro,'" Rocks explains. "That was not the mission statement for a lot of rappers at that time."

"The message was always positive and fun," Segal says of The Cool Kids, adding that the duo served as direct inspiration "for our generation of music makers" and the foundation for his Savemoney collective.

"We came in and we kicked in that door and we opened the door for a lot of other people" to be themselves in their music, Rocks says. "We'll forever be known and recognized and heralded for that. Nobody told us to. We just did that out of our own spirits."

Things haven't been entirely smooth for The Cool Kids over the years. There were legal battles and issues with record labels that stalled the release of When Fish Ride Bicycles. And as Inglish hunkered down in the studio with the likes of TV on the Radio's Dave Sitek and Incubus's Mike Einziger working on his 2014 solo debut, Convertibles, and Rocks released Banco, his own solo offering that same year, it seemed the group might be over. In July 2015, Rocks even indicated as much taking to Twitter to say the group was "never coming back." Only a year later though that all changed when Inglish formally announced on Twitter that The Cool Kids were officially back.

Talking to them now, both members will tell you it was only a matter of time before they reunited. "We always had that intention," Rocks says, noting each of their solo projects were "a means to an end at that time to keep ourselves sane." Having each spent the ensuing years honing their craft, each also felt more confident when returning to the group. "Back in the day we were less inclined to [experiment with our sound]," Inglish says. "I wasn't as confident in my stretching notes and how beats go. We have our own ways of pushing boundaries but we're never not current. We're more current than current."

"We don't put a cap on each other's limits or our abilities," Rocks adds. "If [Inglish] wanted to pull out a saxophone and do it, musically I know whatever he's gonna do he's gonna come up with something that's dope for us. I know if he enjoys playing it it's gonna be good."

Taking a final few bites of that crab cake sandwich, Rocks pauses to smile when asked what the future holds for The Cool Kids. Were the years in the wilderness worth it to get to this current place? "Absolutely," he says. "I went through all of it for this moment. I did it for us. For that kid that felt that way that didn't know he could do it. It feels good to stand on top now after going through that storm."

Inglish, however, isn't pleased with that response. "Naw man," he says with a smile. "Singing your accomplishments when you ain't even close to being done is weird. Let's just say we're starting now for the first time."

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