The year is 2005, and hip hop was in a weird place. Rap as a genre had produced some of the best albums to date. Timeless classics like Tha Carter II, Late Registration, and The Documentary had dominated the charts. In the less mainstream side of the rap world, names like MF Doom and Sean Price had been making waves. Overall, we got a lot of incredible music from that era, and I don’t think anything was done wrong. But it felt like something was missing; something new and fresh. For the most part, all our top rap stars had been famous and killing the game for years. New York and the South had set the standards, and all the new artists were trying to replicate their formulas. What the world needed was someone who could help usher in the new era. Someone who didn’t want to follow trends. As I spoke to Sir Michael Rocks, it became more and more apparent to me why he became that missing piece.

The pseudonymous rapper Antoine Reed was born and raised in Chicago, where he quickly learned one thing I think we can all agree on: Michael Jordan rocks. That simple fact was really all it took for him to want to be known as Michael. Even as far back as kindergarten, he would write Mike on his school papers, much to the dismay of his teachers. Mikey Rocks as a rap name really explained itself; he just wanted to add himself to the list of great Mikes.

“People train to go to the NBA,” he said. “People get trained to be a lawyer because their dad’s a lawyer, but my family… they taught me to be a rapper.”

From a young age, he was introduced to rap music and taught how to understand and appreciate flows. By 9 years old, Michael was rapping, memorizing flows he liked, and learning what he could from every piece of music he was shown. By high school, he was taking production classes and reaching out to other artists on the internet. He met Chuck Inglish via Myspace, and they bonded fast from a mutual interest in production, hip hop, and artists like Little Brother, Lupe Fiasco, and Mickey Factz. It was like magic after that; they formed The Cool Kids and everything started falling into place. By the time Mikey was getting out of high school, The Cool Kids were starting to gain traction. He made plans to go to college near Chuck so they could spend more time together and really focus on music. But by the time his first semester of college was over, The Cool Kids had become so big that Mikey was almost forced to drop out of school.

“It was really kind of in the stars for me to be a rapper,” he said. “By the time I met with Chuck we had a strong plan as far as how we would do this. Because we were real big students of the game. We bought all the XXL magazines, The Source magazines, Scratch magazines… So when we started to blow up, we really weren’t that surprised. We were happy; yeah we were definitely happy; but we weren’t that surprised.”

The Cool Kids were part of the first generation of DIY rap. They were at the forefront of self-promotion through the internet. They came to prominence in an era where people were still reliant on radio placements, cosigns, and handing out mixtapes. Their DIY entrance made it feel like the music industry was changing. The Cool Kids signed with Chocolate Industries in 2007. This brought them opportunities that seemed like dreams come true. With songs featured in video games like NBA2k, TV shows, and numerous commercials - including a memorable Nike ad with Lebron James and Kobe Bryant - their music was becoming unavoidable. This success went on for a few years, and through their label, they released a few tapes and announced an album. However, behind the scenes, things were not great. The album had been delayed for years, and their creativity was being stifled. Times were once again changing. The industry quickly learned how to capitalize off of the DIY online movement created by artists like The Cool Kids, and the uprising of streaming services like Spotify quickly reminded everyone how little you need to pay artists. With money on the forefront of the minds of executives, they believed The Cool Kids’ backpacking-party-music image just wouldn’t cut it. The Cool Kids were being asked to do things outside of their comfort zone and outside the realm of what they wanted to represent.

“Let’s get you guys an Alicia Keys feature… Like, why the fuck would we have an Alicia Keys feature on our album? That’s just not us… We are The Cool Kids; we represent a skateboarding retro hip hop party music group. So shit like that we just refused to do, and that didn’t go over very well. I think they took that as a slap in the face a little bit. That’s when things like Spotify started to develop as well, and all that payola and label controlling shit started to creep back in slowly - and it’s like the indie shit is dead. And that’s still how it is now; they took all the power back after the indie grass roots era.”

Through a spew of legal battles and contract debates, The Cool Kids did what they had to do and left their record label in 2010 to once again become independent artists. They released projects that had been held back, such as Tacklebox and Gone Fishing. They also debuted their long-awaited album When Fish Ride Bicycles, which featured guest appearances from Bun B, Ghostface Killah, Boldy James and others. The Cool Kids continued to shine for a bit, but the stress that followed would lead to the group’s dissolution two years later. In 2012 it became official: The Cool Kids were no more.

Life took some turns for Mikey Rocks after this. After feeling like they did everything they were supposed to do (like spreading a positive message, turning down the big labels that wanted them to change themselves, starting from the bottom and working their way up) it still felt like they got screwed over in the end. Mikey Rocks had learned a lot. He felt wiser and more mature. The lyrical content changed; this was no longer some teenage kid in the big world, and from now on Mikey Rocks would be known as Sir Michael Rocks.

In 2011, Sir Michael Rocks dropped his first solo project. A 25 song tape titled The Rocks Report. This set off an incredible mixtape run, where he would prove that he was still a force to be reckoned with. There was a time for me personally in 2011-2014 where I felt like Sir Michael Rocks was everywhere, and rapping with everyone under the sun, including artists like Mac Miller, Freddie Gibbs, and Currensy. He would follow his success, moving around from Chicago to LA and Miami, and traveling to places like the Dominican Republic and Puerto Rico. In 2014 while living in Miami, his first official album would drop, titled Banco. Inspired by the name of Banco Popular, a bank in Puerto Rico and the Dominican Republic, which translates to "Bank of the People", this album was not only a statement, but a work meant for his fans. Myself being a resident of South Florida when this album dropped, I remember hearing it and being blown away. This was a different Michael Rocks than what we had seen before. The South Florida influence was strong, and the music seemed to be exactly what we needed to hear.

By this point in his career, Sir Michael Rocks had learned how to navigate through the music industry, and was purely focused on doing exactly what he wants. Every move made now was fully his own decision, back how it was when things first started and he had total control. However, he also realized that he missed working with his old partner Chuck Inglish. Therefore, through a combination of growth, personal desires, and wanting to finally do things on their terms, Sir Michael Rocks and Chuck Inglish shocked the world in 2017 by reuniting as The Cool Kids. The rap world was delighted to hear the new music from a group that many thought of as a “what if?.” The nostalgia alone garnered the attention of many and brought The Cool Kids back into the light.

By 2020, it’s hard to think that Sir Michael Rocks has already been in the game for nearly 15 years. When you’ve been doing things that long, there is always going to be fans that remind you how much you’ve changed. In an effort to prove that through change, he had really remained the same and just gotten better, Sir Michael Rocks released “Broken Window Of Opportunity” in 2020.

Songs like “You Can Do It” shine bright as a positive reaffirming voice from someone who had lived it all, and was a stark contrast from the aggressive negativity often seen in hip hop. He and I both agreed that this is the best music of his career so far. A repeated sample of a news reporter explaining ‘the broken window theory’ accompany several tracks on the album that are meant to remind listeners of how important it is to take care of ourselves, as well as gives the album it’s namesake. The lyrics boast the ideas of staying true and acceptance, while reminding you to understand who you are. His sing song hooks and flows, on tracks like “Exotica Maximum” and “Tryna Hide”, remind the listeners of his laidback early days and what made you love Sir Michael Rocks music in the first place.

Meanwhile, he also reconnected with his old partner Chuck Inglish. As a result, The Cool Kids returned again in 2022 for a three-part album, titled Before Shit Got Weird . Given what The Cool Kids had gone through, how much they had watched the industry grow and change, and everything they had learned since their split ten years prior, it was the perfect name for their album. The first words heard on the album are Michael Rocks saying “Six! Y’all ain’t heard that in a second huh?” , a callback fans would recognize from his early days, and a reminder that The Cool Kids were back, and still true. This effort showcased the braggadocious, confident side of both artists that was familiar and welcomed. It highlighted the same type of fly and cool lifestyle that made them both so fun to listen to in the first place.

Calling Sir Michael Rocks a rapper would be a disservice and a slight to who he is. He is an artist and a visionary. What he is, is a true creator. Throughout his career he’s extended past what it means to be someone that makes music. All of his cover art is either done by himself or curated to his exact liking. He’s the same child that loved drawing, designing, fashion and making music. He understands that he’s lucky to not be making music for survival. It’s aways supposed to be fun, something he feels passionate about, and something he enjoys doing. Marriani, is another one of those passions. A high fashion clothing brand in which Sir Michael Rocks designs everything from step one, to cutting and sewing final products.

“I just know who I am. People, especially other rappers, they respect me more for my clothing than what I’ve done for music. Like, I couldn’t get ASAP Rocky on a song with me, which is cool; I get that I’m way smaller than him and there may not be value; but I know I could get ASAP Rocky in a leather jacket I made... As I get older, I’m just kind of realizing more and more what I need to do and what’s actually moving the needle for me. When it comes to thinking of longevity and the future for me, career wise I think fashion’s gonna take me a little farther than my music will. We’re very numbers based as an industry right now, and I’m not the numbers dude... I’m not gonna lie; I don’t get a billion views on my shit. That ain’t really my thing; I’m just not trained for that; but I’m not bitter or angry. I understand and respect that. I just know what my strong points are now.”

Since its inception in 2012, each collection from Marriani Clothing show that Sir Michael Rocks’ finger is on the pulse of the world more than ever. This year, Sir Michael Rockss plans on moving to New York to attend a prestigious fashion design program, so that he could continue to focus on creating artwork in every way possible. He has always seemed to be a step or two ahead of the rest of the world, and if he continues to do things with the love and passion that he always has, nothing will change about that.

“Life has been a journey of learning to not take shit personal... To get where I am right now, that journey would’ve destroyed a lot of people... I look at it all now, as i am in this current state; I’m the strongest and best version of myself. I am not able to be broken down by SHIT! Everything I’ve been through; all those things have toughened me up; I’m more talented and smarter than I was before; and I’m excited for the next steps. I love the rap game, and I’m always gonna be doing this; but I won’t expect the rap world to cure all my problems. Im too logical… I make what I want to make, for fun.”

As always, I asked Sir Michael Rocks his top 10 movies:

• 1: Widows (featuring the acting debuts of Sir Michael Rocks and Chuck Inglish!) (2018)
• 2: The Florida Project(2017)
• 3: The Matrix (1999)
• 4: Terminator 2: Judgment Day (1991)
• 5: Paid In Full (2002)
• 6: The Holy Mountain (1973)
• 7: All About The Benjamins (2002)
• 8: The Grand Budapest Hotel (2014)
• 9: Kickboxer (1989)
• 10: Tales From The Hood (1995)