This time around in our size? sessions (20:20 Mix) series, we welcome none other than Bobbito Garcia – aka @koolboblove – into the fold for mix number 9.

A true multi-faceted titan of the sneaker, hip hop, streetball and film making community, it’s an honour to have him laying down a 20 track mix for us on Friday 29th May.

We were lucky enough to have an in-depth chat with the man behind the mix, discussing all things footwear, music and film making.

What’s your very first memory of anything footwear related? What kinds of shoes were you wearing before you really discovered the ‘cultural’ aspect of sneakers within hip-hop? 

“My humble beginnings, born in New York in the 1960s, getting conscious of what the footwear movement was in the 70s, really allowed me to cultivate an early lens on this whole culture and I’m grateful for it.” 

“I wore Skippies for nine years! Skippies were like the ‘non-brand’, off the rack bargain shoes that your parents buy. My mom was in the mountains of Puerto Rico on a farm barefoot when she was a child, so it would’ve been nothing to her if we would’ve been barefoot. Not that we were rural poor, we were working class. But it wasn’t important to her to necessarily make sure her children were forward thinkers when it came to fashion at age 7/8, in the way that a parent now would engage with their child from infancy, and having their children wearing brand name shoes… that wasn’t the case back in the ‘60s and ‘70s.” 

When you started playing Pick Up Basketball in New York, were there pairs that you vividly remember people wearing on the courts? 

“Of course, it’s heavily detailed in my book ‘Where’d You Get Those? New York City’s Sneaker Culture: 1960-1987′ [Testify Publishing, 2013] where it details a 27 year period – every shoe that was relevant on the courts of New York, specifically, because that’s where I grew up, and not just the shoes that were the basic performance shoes, but also the rare gems, and the intriguing matter of what we used to call the ‘Slept On Butters’… 

“So when everybody thinks basketball in the early ‘80s they think of adidas Top Ten’s, Nike Blazers, but then if you were a ballplayer and heavy into the sneaker culture already, you weren’t wearing either of those, you were wearing Nike Franchise, or you were trying to go with a new brand like PONY who had the Bob McAdoos and the MVPs, PRO-Ked Final Fours, which was a shoe that was similar in design to a Top Ten.

“Back then our goal in New York was to be completely unique, very different to the modern era when Nike is the predominant brand and everyone wants to wear the latest limited editions because they’re all across the blogs and everything. Back then, if you look in my book, there’s photos of teams that I played on where every single member had a different pair of shoes on, and if there were two pairs of Nikes, then it would be two different models. Whereas you could see a photo today of kids playing ball and a whole squad might have Jordans on. So it was a very different era and a really sharp approach towards what we wore.” 

Obviously, with playing on the street courts people wanted to prove they were the best ballers, was there a sense of one-upmanship as to who had the best kicks as well? 

“Of course, that was a daily challenge! That’s the foundation of how this whole craziness starts. It doesn’t start in fashion it starts in basketball. The one-up competition comes from basketball and that lends to the street, and eventually to Hip-Hop, and eventually to the whole world. So the ‘incubator’ was sports first, because all these shoes that are so prominent and iconic were performance shoes at one point. 

“If you look at the Rod Laver or Stan Smith by adidas; hardcore tennis players wore those. You look at the Air Force 1, Air Trainer, Air Max, those are all shoes that were worn by top athletes and designed for them as well. You look at the Jordan line, the Jordan 1 wasn’t well designed, but the II, III and IV moving forward were supremely designed for function and style – and, obviously, the greatest ballplayer that ever lived wore them. 

“That whole challenge comes from a basketball mindset. Even Phil Knight the founder of Nike will say they ‘started off as a running brand, but the soul of our company is basketball.‘ – 100%. We were the sport that catapulted this thing over the top.” 

What was the point that you started to become known for having an interest in shoes, was this the same time the radio show started blowing up? 

“I never had a lot of shoes, not in that era and not now, I wouldn’t consider myself a collector. I was a person who had a keen eye for what I was wearing though, and I also customised – dating back to the late ‘70s, early ‘80s. 

“So if we’re talking about one-upmanship, people couldn’t compete with me because I could paint, and I could paint a colour that not only wasn’t available in our city, I could paint a colour that brands hadn’t even thought to combine yet. I was doing three colour combinations on Air Force 1’s before Nike was doing them, years prior. 

“When I started hanging out at clubs in the late ‘80s, I quickly got a rep for sneakers, and that’s what led to the Source Magazine, which at the point was the bible for Hip-Hop culture. But they had never had an editorial about fashion, and the Editor in Chief asked me to write an article about sneakers. So I penned ‘Confessions of a Sneaker Addict’ in 1990, which was published in ’91, and that was the start of sneaker journalism. It doesn’t exist before that. I am the creator of an entire industry. Hypebeast, SneakerFreaker, if you do a family tree it all comes back to that article in 1991.” 

Did you have an eclectic mix of sneakers that you were into at the time, or was the majority more basketball orientated? 

“I’m a ballplayer, so I spend a lot of time playing a lot of basketball, so naturally, the majority of my available shoes to wear are going to be basketball, so that I can go the park and play, or if I’m on the road DJ’ing I’m going to want to play ball at some point. 

“I can be in Oslo, Johannesburg, it doesn’t matter, I’ll want to play ball! So I’m always going to try to lean towards wearing basketball shoes, but I love running shoes. They’re light, comfortable, great to DJ and travel with, also easier to take off as they’re lo-cut usually. Running and basketball are probably the two categories I’ve dealt with the most over the years.” 

Looking through your shoes you’ve sent across to us they all have some sort of meaning behind them, do you have others that you keep which have sentimental value to you? 

“Yeah for sure. Each one that I wear has a ‘moment’, and that’s why I own them. Whether it’s the shoes that I wore in the And1 Mixtape tour in 2006 when I played in Puerto Rico, or it’s a pair of shoes that I wore in a pick-up Game in Crown Heights, Brooklyn where I live, or the Converse G4’s that I recently received during this Pandemic, which has been a very harsh, challenging time to stay positive, and receiving a new pair of sneakers to jump rope in and work on my ball handle was actually really well timed! 

“I’ve been burning out the sneakers I have. I’m very happy Converse are making performance sneakers again, because at one point they turned their back on my community almost a decade ago when they stopped that category. 

“I think everyone has a story when it comes to their shoes and why they’re special, why they’re attached to them, and I’m no different. And the sneakers that I don’t have special attachments to? They move on. I donate them to various non-profits globally that support disaster areas or communities that lack resources, and to me, that’s where it’s at. I’m not a hoarder, not a collector, just try to wear shoes that are important to me.”

Moving onto music, your show together with Stretch Armstrong was renowned for shining a light on so many artists who are now ‘mainstay icons’ within Hip-Hop. Do you ever wonder about any ‘What If’ moment, if you’d never listened to a demo, did artists still have ways to make it somehow? Obviously, the channels were very limited back in those days. 

“I think had Nas, Biggie, etc. not come up to our show, they still would’ve blown up as they were all very talented. We don’t take responsibility for their careers, we just gave them their first public appearance in each case, and we certainly were a piece of the eco-system which created these careers. 

“In other cases like with The Fugees, they weren’t getting any love on Radio until they came up to our show, and afterwards their Columbia rep was able to say to people ‘They were on Stretch & Bobbito’, and then they were able to get on other College Radio shows and from there that sort of catapulted their career. 

“There are certain cases like Artifacts, who were specifically discovered on our Radio show, and wound up getting a record deal because of it. But when you talk about Eminem, Jay-Z, a lot of those artists were on track to become stars, but they all knew, and it was just part of the ‘scene’ that you had to come up to us first to get that sort of blessing. Not just from me and Stretch, but from our audience. Our listenership was number one in the world. They were the most die-hard. So you had to pass through that. 

“People called us ‘Gatekeepers’, we weren’t the gatekeepers, it was our audience. Together we were the vanguard.” 

How many demo tapes do you reckon you were getting through each week to find the cream of the crop for each show? 

“I don’t know how many Stretch was listening to, but I was listening to at least 100 records a week. 1 demo might have 12 songs on it and 11 might have been shit, but one might have been that incredible track. 

“It was a weekly chore because most of the stuff that we would go through and listen to wasn’t that good, but then there were those gems, and that’s what we comprised every show with. 

“That show was highly curated for 12 years. Stretch and I did it together for the first 8, and then I did it with Lord Sear from ’98 to ’02, but those 12 years on WCKR was the very best of Hip-Hop music that you could hear.” 

Were there any artists that appeared on the show that you ended up signing to Fondle ‘Em Records? 

“Nah, I didn’t sign any artists to Fondle’ Em. Fondle ‘Em was a really beautiful platform, and I would give artists 50% of the profits. They would retain the rights to their Master recordings, all the publishing. It was unheard of for a label to treat artists that favourably. I just wanted to put out good music, it was basically like licensing deals, without any agreements. We just did it all on handshakes.” 

Obviously, a big part of your life now is also documentary filmmaking, you’ve had a very successful career with it so far. As a filmmaker its very inspiring to watch the way you put them together, have you always had the DIY mindset going into these kinds of projects, stemming from what you guys were doing on the Radio as well? 

“I’ve been DIY my whole life, even before the radio show. My first job was at Def Jam. Granted we were distributed by Columbia/CBS, which eventually got bought out by Sony, but we were an independent label.

“When I started working at Def Jam there were 13 or 14 employees in the whole office, for a label that was globally famous and selling millions of records. So I knew how to do things DIY from Def Jam, and when Stretch and I got on Radio, I used all my marketing ideas to help promote the show. 

“I’ve put out three films this decade completely self-produced, self-funded. My first was ‘Doin’ It In The Park: Pick-up Basketball, NYC’, the second was ‘Stretch and Bobbito: Radio That Changed Lives’, and third was ‘Rock Rubber 45s’. 

“Now think about the fact that I produced, wrote, directed, music supervised, was the marketing director, social media director…we hired independent publicists but I probably got half of the press myself for those films. I mean I’ve carried a load on my back, and spit out three films in basically 8 years.” 

It’s impressive! 

“It’s insane. I’ve a lot to show for it. ‘Radio That Changed Lives’ premiered at the London Film Festival in 2015, we had 2 sold-out shows. 

“For ‘Doin’ It In The Park’ we did probably over 180 screenings around the world! 

My last film ‘Rock Rubber 45s’ was selected by the Smithsonian for their first African-American Film Festival and got the New York Times’ ‘Critics Pick’ so I’m very proud of my films, and people will forever talk about what I’ve done for sneakers and with Stretch on the radio show, but I always like people to talk to me about my films!” 

I think the way you went about handling everything yourself probably helped project your vision without having too many other hands getting in the way, you can keep things your own way from the start. 

“Going back to sneakers, I was a music consultant for what was almost the first sneaker documentary, before ‘Just for Kicks‘ [which I would say is the very first, and was very well done]. 

“Before that, there was a doc that was being produced by Nike and I believe Wieden + Kennedy were involved as the ad agency, and they’d brought me on to be a music-supervisor, and things just got caught up in corporate red-tape and it never came out. 

“So that’s just one example, I have plenty of them where brands have their own agenda, so I always feel like it’s a better move for me to just not pay any attention to soliciting sponsorships or whatever. I’d rather just do my projects. There’s one bottom line that brands need, and that’s authenticity, and that’s what I provide, I’ll never compromise myself in any culture, not in sneakers, not in basketball, not in music. 

“I’m going to be 54 in a few months, that’s a long time to have done this without having to bend over backwards to be partnered with something, and also a long time to do this without having anything that people can hold over my head. Look at everything I’ve done, I’m very happy about that.” 

That’s the best way to be.  

Finishing off with one of your most recent projects you’ve been working on with Stretch and the M19s band. It seems like a really interesting ‘full circle’ project that looks back at both your Latin Jazz heritage and Hip-Hop and combining the two loves together. 

“Yeah, that’s a good way to describe it.” 

What was the story behind having the initial idea for that project? 

“I collaborated with Eddie Palmieri on my film ‘Rock Rubber 45s’. I produced the title track to the film. Eddie Palmieri’s an 11-time Grammy award winner, and so his label was like ‘You can produce! What do you want to do with this?’ and I was like ‘I don’t know, I’d love to do an album! Why don’t we do it with Stretch?’ So we put a band together and the wheels started moving behind that. 

“With the help of Eddie’s label, we put together an elite group of musicians, then Stretch and I sat down and discussed what songs we’d like to do. We did some original compositions as well which will be on our second album. 

“The debut album is titled ‘No Requests’, and it was released back in January. We had our debut concert at the Kennedy Centre which is the USA’s official cultural centre which was huge! We were about to go on tour to promote the album and then the pandemic hit, so it’s a weird time. 

“We have some new releases coming out this summer. We’ve been able to figure out how to create acapella versions of the Big L and Jay-Z freestyle from our radio show in the ‘90s, also the Method Man & Ghostface freestyle, Biggie’s, etc. so we have our band creating new music for these freestyles. We’ll be releasing the original versions digitally re-mastered, and then new versions with our music, and I’m very excited about both so people should be on the lookout for that!” 

What kind of direction do you think you’ll take with your size? sessions (20:20) mix? 

“Haven’t decided yet! Me and Stretch do an IG Live show every Thursday which has been fantastic to return, not to the ‘airwaves’ but just to return to doing a weekly music-based show. 

“As our audience is predominantly hip hop, I’m not going to play a Louie Vega house record, at least not yet! But my tastes run pretty wide, as does our audience, but right now we’re kind of weaning them. 

“I think with the size? mix, I might flex more my world/jazz/soul muscle a little bit more than what I would with myself and Stretch’s show. So I’m looking forward to it!” 

We’re looking forward to hearing it!