ARTIST OF THE WEEK: DEREK BRENNAN
WORDS: Stu Gomez
Most of us aren’t content to express our love for skateboarding by simply skateboarding. We sometimes need other avenues to channel our passion (some would say “obsession”) for it. Artist Of The Week Derek Brennan pays tribute to skating, and the pros who have steered the culture’s trajectory, with his series of Pro Skateboarding trading cards.
Read our interview with Brennan below to learn about his labor of love.
How did you become interested in art?
Art has really been a part of my whole life…I’ve just always been a very visual person. Growing up I didn’t want to read the books in school—I just wanted to look at the pictures or find a video/movie alternative. Visuals just captured my attention. So things like children’s book illustrations and cartoons were some of my earliest artistic influences. I can remember being 4 or 5 and trying to learn to draw a lot of those characters (primarily the Teenage Mutant Ninja Turtles). I got a lot of practice in drawing… then people started to tell me I was pretty good at it, too. I think that fueled me even more, like, “Oh… this is what I’m meant to do. This is my thing.” I haven’t stopped since and it’s really morphed into an interest in many different types of art: painting, design, photography, film, etc. There’s a lot of carry-over.
Board graphics for The SunnySide Company 2016.
What’s your history with skating?
I started to notice skateboarding in 5th or 6th grade (1998-99), but it took a lot longer for me to actually dive into it. At first it was just seeing kids bring CCS catalogs to school and hearing them talk about everything in there. Like, someone would mention “the new 411” and I was like, “What? That number you call for information?!” I was clueless at that point.
Then my best friend had an older brother that got heavily into skating. So my friend would get his old setup sometimes and would try to learn tricks. I tried a few times but, really, if I was gonna be outside I wanted to be playing basketball—that was my obsession at the time. I continued to know kids that skated all throughout my school years, but it wasn’t until towards the end of high school that I finally started to get really into it. It was a combination of the Tony Hawk video games and the CKY videos that finally flipped that switch for me, as funny as that might be! Then, friends introduced me to actual full-length skate videos. My first five were probably: One Step Beyond, Modus Operandi, Jump Off A Building, This Is Skateboarding, and Yeah Right. Menikmati might have been in there, too. After that, I was hooked. Everything just looked so cool: the clothing, the tricks, the spots… and, of course, the board graphics, ads, photos, etc., really appealed to my visual art side.
How did you hit on the idea for trading cards?
As I mentioned earlier, I was really into basketball as a kid. Growing up in the ’90s, there was a big boom for sports cards. So my older brother and I had huge basketball card collections. I saved my favorite ones even after I stopped collecting. Around 2013, I found my collection and started looking up their value online. I soon discovered they weren’t worth what they used to be (the sports card boom had long been over). But the plus side was that I could now buy cards that I wish I had as a kid for a fraction of the price. So that actually kind of got me into collecting again because it was so nostalgic.
I somehow got ahold of one skateboard card around then—a Josh Beagle Big Brother card. And then in 2016, I made a mockup of a Heath Kirchart card with info and photos from an old interview of his. So the idea has been in my brain to some degree since then. This whole time I had continued to make art, mainly portraits. Over my life I went from drawing my favorite cartoon characters to drawing my favorite basketball players to drawing my favorite skateboarders. I had made a few stickers of some skaters I’d drawn and would sell/trade them. I liked the tangibility of those as opposed to just sharing my work digitally. And similar to the basketball cards, I liked that I could collect stickers and they wouldn’t take up much space.
Then… it finally clicked: I should turn these sticker portraits into trading cards. I made one of Gonz first and posted it on social media. Another illustrator I follow, Alex Perry, suggested I do more of the Krooked team (the LSD video had just come out), so I did one of Brad Cromer next. People seemed to really love the idea so I began making them regularly. For me, they became the perfect blend of my hobbies past and present: skateboarding, art, design, basketball, and card collecting. Many of the layouts are inspired by old basketball cards from my collection.
Gonz watercolor 
The trading cards project is so dope. Do you have any advice for artists who may be having trouble finding their own niche?
Thank you, I really appreciate that! First, I would say—make what you feel you are called to create or what you feel passionate about. If you’re just making things to try to fit in somewhere, I’d imagine you’ll get burnt out. For me, once I found the right creative space the ideas flowed pretty freely from there. Then, once you find that space, try to put a unique twist on what you’re doing. As with everything these days, art and design are oversaturated. So check out what other artists are doing and look for opportunities to do something a little differently. Lastly, I would say—be patient. These days with technology and social media it’s easy to want instant results. But not everything happens that way. Don’t get discouraged, just keep doing what you’re doing…keep shaping and refining that thing. Eventually you’ll find the right place for it.
Check out Derek Brennan’s site for more info about his Pro Skateboarding trading cards series.
Gino Iannucci for series 4