Hosted by Highsnobiety’s Editor-at-Large Christopher Morency, “On the Record” is a podcast series of intimate, off the cuff conversations with icons and cultural engineers that have shaped the worlds of fashion, music, tech, art, business, sports and youth culture at large. For this episode, Morency spoke with New York radio, sneaker, and streetball icon Bobbito Garcia.

Bobbito Garcia aka Kool Bob Love aka DJ Cucumber Slice has long been a New York City icon. From his early days of hosting the legendary alternative hip-hop show “The Stretch Armstrong and Bobbito Show” throughout the '90s which aired unsigned artists, rarities and B-sides from commercial artists and played in-studio freestyles from then unsigned legends including Nas, The Notorious BIG, Jay-Z, Wu-Tang Clan, Fugees and more, to his pioneering 2003 book on sneaker culture Where’d You Get Those?, Garcia hasn’t documented youth culture from afar, he was there.

And there’s more. Over the past three decades he’s published magazines on streetball, hosted podcasts on NPR and brought sneaker culture to ESPN. He’s produced documentaries, worked with Nike, adidas and Puma on sneakers, and runs his own basketball tournament. A true gatekeeper of authority, and influence. And then some. In his New York residence we call him up.

The below interview is a written version of ‘On the Record’ Season 2, Episode 2. It has been edited and condensed for clarity.

Bobbito dude. Radio host, DJ, author, podcast host, director, producer, street ball player and coach, sneaker collector, announcer, shoe designer, gatekeeper of the 1990s hip hop. How would you even describe yourself to start off with?

Bobbito Garcia: All of the above. You did a pretty good job there, except I'm not a sneaker collector. I'm a historian, a documenter, an ambassador of the culture. I penned the very first article on sneaker culture back in 1990 for The Source Magazine titled ‘Confessions of a Sneaker Addict’, but I've never thought of myself or wanted to be considered a collector. An art collector may have a number of paintings that they don't even hang. Similarly, someone may have a number of sneakers that they don't even wear. That's not my case. I'm very functional, and I'm an athlete. I play ball. I run, so I use my sneakers. I mean, I do have some sneakers that are museum-worthy, which I've lent to various cultural institutions, and that I featured in my book, ‘Where'd You Get Those? New York City's Sneaker Culture: 1960-1987’, which was released in 2003. But yeah, I don't consider myself a collector. I don't think other people should either. I only have like 20 pairs of sneakers, compared to others who have that times 100.

I mean, in a way you set us up, even us at Highsnob, being the first one to pen about sneaker culture, and after that with the book. This is something that never existed at that time on paper, but the culture around you was all around. Nowadays, the culture's shifted so much where that market is massive.

Absolutely. I mean, in the 80s, we were living the culture and not necessarily documenting it. There were certain songs, like ‘My Adidas’ by Run-DMC, and there were certain references to sneakers. Nas said, "And I'm a Nike-head," and Ed O.G. and the Bulldogs said, "Put on your adidas and step off. I got to have it." I mean, there were always references. When I wrote my article, it was really the first time that anyone had tried to open the curtain, if you will, on what this lifestyle is and what it means, and what was missing was the why. My book really expanded on that. I didn't write the first book on sneakers, but I certainly wrote the first book on sneaker culture, behavior patterns, experiences beyond the actual shoe. My book was more about the people than the actual shoes.

Today, it's become so extremely mainstream where there's a new launch every single day. Coming from culture into commerciality has always been a tricky subject, but it also offers a lot of opportunity. How do you see sneaker culture today?

That's an interesting question. I think 2020 and moving forward presents the very best time that we've ever had to share and experience sneakers. There are more models out there, there are more opportunities to get rare shoes in other countries that prior, you'd have to travel to, and now you can get stuff online. There's still the limited edition stuff. I mean, it's certainly no longer a secret. When I was experiencing sneaker culture in the 70s, we were like this dark society of people who were completely different from our parents, whereas now, you have parents and children going shopping for sneakers collectively, and it's beautiful to see.

It’s gone mainstream. There are a lot of pluses and minuses to that. I'm born in the 60s.In the 70s and 80s, if we had a pair of shoes, we might trade with our friends, but there was no resale value. In the late 80s, early 90s, there were primarily Japanese and some European resellers that would come to the United States and climb through the bargain bins and the basements of Mom and Pop shops and then bring them back to their respective countries and mark them up.

Did it change for the good?

The internet comes along, and now, you have apps and stuff, and you got StockX and it's a whole other world. It's an industry unto itself. That's good in that, prior, you only really had five groups participating and profiting off of sneakers, which were the manufacturers, the brands, the distributors, the stores and the athletes. Now, you have the sixth group, which is the resellers, some of whom are 12 years old, some of whom are in their 50s. It's a very large community, a very lucrative one, so that's good. People participating in that is a good thing.

The downside of that is that people are participating in shoes that are valuable monetarily doesn't mean they're valuable culturally, or that they're valuable design-wise, right? You see certain shoes selling for a lot of money, and it's a facade. They're not really valuable because the people wore them fresh or anything like that. They're just valuable because they were really limited, and the hype got out of control.

When we speak about this bell curve of influence, it takes time for culture to surround itself around anything. Whether it’s in music, sneakers or sports. Is that something you think that we've lost with the speed of everything?

Yeah. The speed at which things become valuable and the speed at which influencers can affect the mindset of a global community is light speed at this point. Everything has its upside and its downside. You have kids now who can be global influencers with their Instagram page and haven’t ever worn a pair of sneakers, just by virtue of the pictures that they have of their closet. That's unprecedented. You have to think about that. In my era, the only way you got props for sneakers is by virtue of wearing them. No one was going to see what was in your closet. You had to go to the gym, the basketball court, or the street. You had to earn your stripes with hard work, getting out there, and be seen. It's very different if someone's really rich, for example, and they just buy the most expensive sneakers and they take pictures of it, then they're going to receive a following. It's a different way to earn your stripes, or in some cases, you're not even earning your stripes. You're just buying into your stripes. That’s where we’re at right now. There are still people who recognize those who might put in the extra effort to be a [real] influencer compared to those who do it very easily.

Earlier on when we spoke about that whole list of titles you have, many people have that today. Back in the day, was it the norm to do all these different things?

I mean, on a global level, probably not. But, I'm a New Yorker, and I look at my mom growing up. My mom was a hairdresser. My mom knitted wedding outfits. My mom would cater food. My mom would work at a bank, all these things concurrently, and she was raising four kids at the same time. In New York, you have this gene that you're born with of just out-hustle. I was blessed to be born in the 60s so I got to experience playground basketball as it was bubbling on the playgrounds of these five boroughs. I was blessed to experience and witness hip hop in its burgeoning years. Both hip hop and playground basketball contributed to the birth of sneaker culture, and I got to see that from its infancy, right? It wasn't an anomaly to be into basketball, sneakers, and music at the same time. There were a lot of us.

I think of photographer Gordon Parks, who did everything. You think of Paul Robeson who was an actor and a football player. Look, we’re blessed to have a lot of talents, and some of us don't always have the opportunity to express or realize all of them. I was fortunate to have two parents that certainly gave me free reign as a child to explore everything. By the time I got into my 20s. I talk about this in my biographical documentary ‘Rock Rubber 45s’, which basically explains how I became a freelance creative, in three completely separate, but at the same time connected cultures and communities on a global level.

Yes, I'm a DJ, and yes, I'm a filmmaker, and yes, I'm a podcast, TV/radio personality, and yes, I design sneakers. Yes, I've started businesses. [But] I'm not done. I have a lot more projects coming up, and I go at them hard in each way so that people can enjoy them on a worldwide level. I'm always grateful that I have that voice.

And shout out to your ESPN ‘It’s the Shoes’ which aired in the mid-2000s.

Yeah. Along with being the first person to ever document sneaker culture in publishing, I'm also the first person to ever have a television series in media history about sneaker culture. I'm at the forefront of a lot of movements for this culture. Look, some people might say I'm lucky. I think I've created my own good luck by virtue of pushing all that I have for as long as I have.

Now, we also have Instagram Lives and your album, ‘No Requests’ came out earlier this year in January. Are you also still an announcer for Full Court 21? What else?

Yeah. Stretch [Armstrong] and I like the whole world unto itself, right? We had the radio show back in the 90s, then in 2015, we released the documentary about that era. It got on Netflix right at the same time when that platform started reaching 192 countries. That went really wide, and Stretch and I have not only rested on our laurels of what we did in the 90s. I mean, currently, we have an album with the M19s band, titled ‘No Requests’. It's world, jazz, soul, funk, very Latin asshole music. We had a whole tour lined up, but then the pandemic hit. We're going to be releasing some new stuff this summer. We’ve also figured out how to extract a capellas from our classic 90s radio show, the freestyles. The Big L Jay-Z freestyle, the Method Man Ghostface freestyle, the Biggie freestyle, all of which are featured in our film and more. I'm going to be executive producing, and we'll be rolling out multiple freestyles for the first time ever, digitally remastered, available on all platforms with proper licensing and publishing, so the original artists and everything. This is unprecedented. It’s all in conjunction with me and Stretch's 30th anniversary of our radio show that we started in 1990.

What we're doing is basically taking the past and connecting it to the now, because me and Stretch, if you listen to our DJ sets, if we're spinning in clubs, or if you listen to our Thursday night show, it'll probably be on Instagram Live, but we're going to start branching out with other platforms as well. Essentially, we're playing music across the board. We're not stuck in only playing rap music. That's what our album, ‘No Requests’ with the M19s band represents. That's what we'll be doing with the freestyle a capellas as well. We'll be releasing the freestyles as they were performed in the 90s. We're just going to be boosting the levels and remastering them, and then we're also going to be presenting the remixes.

Then, we also have a lot of things lined up for our 30th anniversary in the fall right around the actual first air date which was October 25, 1990.

Dude, 30 years of the ‘Stretch Armstrong and Bobbito Show’. Is that crazy to say out loud?

Yeah, I don't know. There are certain elements of the 90s that feel very distant, and there are certain others that feel very present. When I listened to Big L Jay-Z freestyle, that's the most listened to live moment in hip hop history, pretty much. For years, it was getting 10 million, 12 million views on YouTube. Funkmaster Flex has played the Big L Jay-Z freestyle on his radio show, and now he's selling it as if it was a released song, and all it was, were just freestyles on our radio show. It still feels like it's current, even though Big L passed away in 1999, may he rest in peace, even though Jay-Z has moved on and sold 75 million records, I hear it, and he still feels like an unsigned, up and coming artist to me.

I mean, 30 years is great to have under my belt. It definitely allows me to have some confidence about my contributions to hip hop and beyond. I'm just looking to build on that, that's all, and looking to continue to introduce what me and Stretch did in the 90s as well as what we're doing now continually to new generations who weren't alive back then. That's what I did with my book.

The crazy thing is, just to quantify the impact, according to The Source, the total record sales of MCs who premiered on the ‘Stretch Armstrong and Bobbito Show’ exceeded 300 million. That's crazy.

And that was calculated back in 2015. Who knows what that number is now? Eminem released a new album since. It's crazy, but look, we don't quantify our contribution in metrics of financial sales. It's what's measured, and that's why, when I directed the film, it was as important to me to interview Busta, Fat Joe, Nas, Wu-Tang, as it was to interview our listeners who nobody knew, but they were loyal and they were this clandestine community that really experienced something culturally that can't be experienced today.

I remember one of the anecdotes from that film. When they spoke about the tapes and the whole analog idea of having to send them around the world, and in a way, really creating the internet before there was one. Now hip hop, like sneaker culture, is mainstream. What do you think of its evolution?

I'm not fit to answer that question. I'm going to be 54 in September. I think that question is best served to be asked to someone who's in their teens and 20s, who's in the thick of it. I'm a parent now.

I juggle a number of careers. When I was in my 20s, hip hop was my child. It was like, "Okay, I'm going to do everything I can possibly do to carry this child and nurture it and watch it grow, and that's what I did. If you watch my film, Rock Rubber 45s, I was hosting the open mic events for Unsung MCs. Had the radio show with Stretch. I was writing columns for Vibe Magazine and for Rap Pages. I was just doing everything and anything I could to support hip hop. I can't do that now at age 53. I mean, I do do projects. There are people who hit me up on the DMs, and say, "Hey, I want you to listen to my song and see." Okay. You can hire me to consult. I'll listen to your song, I'll give you feedback, but if it's going to pull me away from my time with my son, it's got to be worthwhile.

I'm not 25 years old anymore, listening to 100 demos a week to prepare for a radio show. It's just a different timeframe, but for those who do hire me as a consultant for their projects, they got some amazing feedback from me, because I've lived this. I've been hearing people rhyme since 1977.

Do you still find time for basketball?

You’d mentioned 'Full Court 21'. I'm the founder, announcer and director of a basketball tournament that's played in 30 international cities. I started it in 2013 here in New York, and it's since expanded to four continents, and unfortunately, it was canceled in Japan. It was canceled in Taipei, it was canceled in Hong Kong, Costa Rica canceled because of the pandemic. To all my ball players out there hoping to have it come back in 2021, I mean, there might still be some cities that open up by the summertime where we might be able to squeeze in a couple qualifiers, but look, so much of what I did in hip hop, so much of what I did in sneakers, my basketball tournament, I was just trying to create opportunities for people to experience this amazing culture that I have been blessed to grow up with. I'm just extending my experiences.

Today, art, design, film and fashion are so connected to hip hop culture, which is obviously a big change in the past decade. Through hip hop and fashion, the next generation is being educated on a lot of these original cultural references.

Listen, I'm thankful to you for this interview, because look, I’ve put a stamp on multiple decades, but this is a new one, and these teenagers who are 15, 16 right now just stepping into this amazing world of sneakers, basketball, music and hip hop, if I'm not relevant, or if I'm not redefining myself, then what I've contributed in the past will only be relevant to those who were around to live it. That's a beautiful thing as well. I don't compromise myself just to be relevant to a 16 year old. But, at the same time, I think I come from an era where we had high respect for the basketball, music and sneaker culture that came behind us. That was part of the culture of being in New York. You constantly sought knowledge so that you could come correct.

There was another saying that said, "So I can come correct," it was like, "Down by law." Down by law was a catchphrase that really encompassed everything that was beautiful about the culture. It was like you're either down, or you're not. If you're not down, then you're not really caring about the culture. If you're down, then you're going to put the effort into learning about the history and learn about what's righteous. In certain instances throughout my career, I've been a vanguard for playground basketball. I've been the vanguard for sneakers. I've been the vanguard for hip hop. I can't play that role in every instance all the time moving forward, but that's kind of like what I was telling you about earlier, when I answered you about current hip hop [culture]. I can't be the vanguard in current hip hop right now. It's not my position, but there are other people who are trying to do that, and I salute them.

Looking at the next generation, what are some points of advice you would give them to maybe cut through the noise out there?

If they're listening, they need to take notes. Pay respect to what's behind you. Do research. Don't just rhyme. Don't just collect sneakers. Learn about the insides and the backstories, not just your own, but of others to get the knowledge. Do your homework. Enrich your brain so that you can carry this forward, and that perhaps someone 10 years from now can learn from you.

My generation may not be around in 20 years, 30 years, 40 years. Who's going to continue to carry the torch? If nobody carries the torch, then the torch dies, right? I think we're seeing a lot of young people around the world really caring about changing cultural movements and redefining them on their own terms. Whether it's relevant to their city or country or language or nationality or whatever it is, it's constantly being reinvented. That's a good thing. I like seeing change. I like seeing transformation.

Breaking through is different today. On one hand, platforms like SoundCloud have made it a lot easier to bypass the traditional rules moving up. On the other side, because it's so open, competition increases so much more.

I'm a cat that plays vinyl. I love analog sound, superior to digital, and I just try to support the artists who care enough about people like me to press up their music on vinyl. Listening to music on digital platforms, it's just overwhelming, and it's just there's an overabundance of it as well. I find my gems on wax. I purposely don't listen to Spotify, because I think streaming is very dangerous. It's like if an artist is getting .007 cents off of each listen, that's horrible. That's not supportive of artists, particularly independent ones, so I rather buy the vinyl, and if it's something that's not available on vinyl that I just really, really have to have, I'll download it, pay for the download. That's how you support artists. The artist worked so hard. It's their livelihood. It's their career. It's just not a way to support your favorite artists, or your favorite record labels, or your favorite genre. It's not sustainable.

Will we ever hear you back on the radio again in the future?

That's up to the radio station to open up the door. Not up to me. I would do it in a second. A lot of radio stations, over the years, have approached me and such, but they only want us to play 90s hip hop [but] we already did that. We already had a phenomenal program that was legendary. It's like, "Why would we do that again?" But, who knows? Maybe a radio station is listening to our Thursday night shows now [on Instagram Live] and hears all the different music that we're playing and says, "Wow. They really are engaging their audience with amazing sounds," and gives us an opportunity, but that's up to the stations. It's not up to us. We would do it.

What are some of the tracks you would play?

I'm not going to tell you. I play vinyl and I play world jazz, soul music, and I definitely lean towards songs and artists that not a lot of people know. A friend of mine, he calls me the anti-Shazam DJ, because for years, he's been coming to my gigs, and he'll open up the app, and the songs that I'm playing don't register. They're not even available digitally. That's my role. I'm not the most technically advanced DJ. I don't cut up records and stuff like that, but just try to make amazing selections. It's almost like a Giles Peterson, where I'm trying to educate the crowd and at the same time move them and make them think.