Gatekeepers, Mixtapes and Real Fans: The Cool Kids Reclaim the Conversation

The Cool Kids have always operated in their own lane. And in their recent sit-down with Bootleg Kev, the veteran duo broke down their journey through music, technology and the ever-evolving culture around them. What started as a conversation about their pandemic-era triple album quickly turned into an insightful reflection on staying relevant, avoiding the algorithm's chokehold and nurturing genuine fan relationships in a digital-first music industry.

In the interview, Chuck English and Sir Michael Rocks reflected on their 2022 release "Before Shit Got Weird," a sprawling, multi-disc project that dropped at the height of COVID-19. Though they weren't able to properly tour the album at the time, the duo called it their best work to date. "We didn't really get to tour that one. I don't think people was outside still," Chuck said, noting how the pandemic changed the way artists could connect with their audiences.

What became clear over time is that The Cool Kids are, in Chuck's words, "more of an outside group." Being out in the real world has brought them back in touch with fans who had been following them for years. "You don't see those people unless you go outside," he said. The group is now selling out shows, with Chuck calling the touring experience a major validation that they are still deeply appreciated, even if the algorithm sometimes hides their work from listeners.

From MySpace to the Algorithm Age

The conversation also tracked The Cool Kids' navigation through various phases of the internet. Sir Michael Rocks broke it down like chapters in a book: the MySpace era, the blog era, and now the age of curated algorithms. He noted how the group once had 5 million fans on MySpace, a number that would be monumental even today. But with the platform's decline, much of their digital history disappeared. "That transition was just a crazy time," he said.

Chuck pointed to a pivotal shift when major labels and corporations took note of how independent artists were thriving online. Around 2014 to 2016, he said, the industry moved from fighting streaming to quietly buying up playlist real estate. "Now it's playlists," he explained. "But they already had the playlists sold up. The real estate was already bought."

Bootleg Kev added an observation that stuck with Chuck: "The blog era had gatekeepers, but they had good taste." Unlike today's data-driven playlist placements, Chuck and Michael came up in a time where tastemakers helped push quality music to the forefront.

Outside the Internet, Still Moving Units

The group emphasized that real-world impact still matters more than digital impressions. Chuck pointed out that many artists with massive streaming numbers can't fill a room. "You got artists with millions of listeners who can't even pull 400 people into a room," he said. That discrepancy, they argue, is the result of artists never having to physically connect with fans. "You never went outside. You never elbowed or dapped nobody."

The Cool Kids, on the other hand, have always stayed connected to the community. From fans bringing vintage merch to shows, to younger listeners discovering their catalog through word of mouth, their success is rooted in physical presence. It’s a return to the basics in an era of digital clutter.

On AI, Samples and the Producer’s Craft

The conversation shifted toward technology, with Chuck offering a thoughtful take on the rise of AI in music. While acknowledging its usefulness, he compared AI-generated music to the preset loops found on old keyboards. "It's the same shit," he said. "Music and AI is very easy to hear. It's not like people are stupid."

As a producer, Chuck values the process of creating something from scratch. He's selective about who he sends beats to and avoids the anonymous pack-sending culture that dominates production today. "You can't audition my shit like that. I work too hard," he said. For him, music should be collaborative, not transactional.

He also broke down how the economics of streaming and sample clearance have made AI more attractive. "You want to sample a choir and clear it? That’s going to cost $200,000," he said. In contrast, AI offers a workaround that, while not ideal creatively, is often more feasible financially.

Remembering Mac and the Era of Real Connection

One of the most heartfelt parts of the interview came when the duo discussed their relationship with Mac Miller. Both Chuck and Mike recalled their time touring and recording with Mac, describing him as someone who deeply understood friendship and creativity. "He just knew how to be a friend," Sir Michael said. "Even though he had all the stress, he was always the one cheering everybody up."

Chuck helped decorate Mac’s LA home and remembered being trusted with creating a welcoming space. The love was mutual. "You don’t get people like him doing this anymore," Chuck said. The emotion was palpable as he admitted he still struggles to make sense of Mac’s death. "I’m still pissed about it," he said. "My brain can’t make sense of it."

Legacy Talk and the Blog Era’s Mount Rushmore

When asked about their legacy, The Cool Kids showed humility but didn’t shy away from giving themselves credit. They named themselves alongside Curren$y and Wiz Khalifa on the Mount Rushmore of the blog era, noting how each artist carved out their lane during a time when streaming was still the Wild West.

The group also spoke on the complications of their early career, especially how their debut album had to be split across multiple mixtapes due to industry politics. "Gone Fishing, Tacklebox, When Fish Ride Bicycles—that was all one album," Chuck explained. It was a sign of the times, when releasing original work outside of a traditional label system was still considered unconventional.

Still, they see the culture coming back around. As the industry shifts once again and physical experiences become more valuable, The Cool Kids find themselves in a position of influence. Their story is not one of comeback, but of consistency. As Sir Michael put it, they “stayed low and kept firing.”