Jake Rupp has long been known as one of the East Coast's most underrated skaters. He became somewhat of a cult hero to many. Jake is in the realm of "your favorite skater's favorite skater." Talk to anyone from the East over the age of say... 28, and Jake's name comes up as one of the kings-of-style and one we all wish got a bigger slice of the pie (remember, a decent pie was actually available back then). His unparalleled flexibility and super pop allowed him to ollie up and over some of the most mind-altering objects. Combine that with his loose and almost gumby-like body movement and you have a skater that looked as if everything came naturally and easily. Jake always looked as if he was having fun while skating and he was one with his board; a confident-cool one might say. He made his mark in between the cities of Washington DC, Baltimore MD, and Philadelphia PA. Growing up on a farm along the boarder of MD and PA we felt it was important to showcase a graphic that not only represented some of the cities Jake was known to skate (Baltimore being his favorite of all), but also an ode to growing up on a peaceful farm that impacted him quite heavily as a skater, a man, and a father. Big-Ups RUPP, much respect!
So Jake, most people associate you with MD, but you are in fact from a small town in Pennsylvania, correct?
-Well actually, the Mason-Dixon Line goes straight through my property. So yeah...I grew up in like the South East PA/North East MD area. The line that divides the states cuts right through, but in reality I spent more time in Maryland in terms of skating, school, family, business, etc.
What was it like growing up skating in such a rural area and when did you start skating? How did you even become aware of skateboarding?
- One of the cool crazy older kids had skateboards that we rode. I spent a lot of time in grocery store parking lots and lots of homemade ramps. I started skating in 89'.
More-Skates Skatepark was close to you; do you miss having indoor parks like that? To me it seemed like there were more of them back in the day, or they lasted longer, or at least there were bigger scenes around them back then.
-Indoor parks in the 90's were a hot commodity; skate crews were smaller back then and maybe not as many. That made everybody know everybody from all the different states up and down the East Coast. But yeah, More-Skates in Lancaster, PA was awesome. Before that there was Spunk park too. Lots of for real legit skating went down at those parks. Many heavy sessions; people would drive hours from other states to skate there and vice versa for us. We'd drive to fuckin' Newburgh, NY to skate that indoor park, so cool though. Good times.
Your coverage over the years has been primarily in the North East Corridor, but you have also spent many years traveling with Element and IPATH during the cultural heights of both brands. What are some of your favorite places you have skated and why?
- Favorite places are Baltimore, NYC, SF, Barcelona, and Japan. They all have sick street spots and they're just raw I guess.
Your breakthrough part was arguably in STATIC 1 by none other than Josh Stewart; however, your part was a secret part after the credits. Did you know that was going to happen? Was there a particular reason Josh did that? I thought it was awesome, kind of like how Tom Penny's part in SORRY was a surprise too. Even though the surprise only works once it's still sick.
-I knew Josh from way back during times in Tampa; he been the homie for a long time. I ended up going on a trip with him, Selego, Meinholz, Mullendore, and Steve Brandi. We went just to skate and maybe get some tricks for his video. I ended up getting pretty much a whole part so honestly it was kind of unplanned and quick. That's where I fit in; I was super stoked for sure.
How was filming for that part? How did it differ, or how was it similar to say filming for something like the Element video with Tosh?
-Man...we were all just younger and those were simply some good friends to travel with, skate with, and live with. It just came so naturally.
Pitcrew's WHERE I'M FROM video was also a major East Coast gem. Who filmed your footage for that part? How long were you guys filming for that project?
-Mark Nickles filmed the WHERE I'M FROM video for Pitcrew. How long did we film for? I don't even know how long to tell you the truth. It was more spread out than STATIC.
During your career you skated for IPATH during its heyday. What was that like and were there any crazy stories from your times with that crew? Grasshoppers, best shoe they ever made?
- IPATH was an awesome team; great friends. We were killin' it there for a minute. Just skating with legendary dudes like Matt Rodriguez was epic. As for the shoes, yeah I just wore grasshoppers all the time; I liked the black on black. With IPATH it was really rad being in San Francisco at that time. We had a lot of fire and a lot of momentum behind us; bombing hills with Kenny Reed, Matt Field, Big Foot, it was just so radical and cool. It was...whatever you want to call it; just real honest, raw, and in the moment. Pretty epic tours to Japan man. Not only skating, but traveling through the the country side as well searching for Buddha and bamboo you know?
The tweaked-out ollie was somethig you personified over the years; allowing you to go up and over some incredibilty tall objects. Was pop and flexibility something that you always had in your skating or did it develop over the years? You got a secret to pop like that or is it a "you either got it or you don't" kind of thing?
- I just like ollieing over things. The feeling of floating over objects felt so awesome. I think it's just being flexible I guess?
- I just retreated home, had two kids, which has been awesome. Going on strange journeys...some light some dark.
What are you up to these days? Where have you been skating and what is your daily routine like?
- I skate at some local parks like York park, skate some local city spots, chillin', trying to eat better, farm life, doing tile-work on the regs. Putting good stuff into my body; trying to teach that to my kids. I've been in the food business with my family for a long time so eating well is important to us. My grandmother is from Kentucky and started a restaurant here 55 years ago that my mom ran. She just sold it though, but it was Southern food made from scratch. Chicken, corn fritters, super good stuff.
You joined the world of social media only about a year ago, but during your leave you mentioned to me that you were not keeping up on the day-to-day of skate media. Now that you are more involved again, what's your take on it all right now?
- Yeah I just got on social media a year ago; specifically to reconnect with my skateboard family. It's cool to see everybody living and ripping. I like seeing the local rippers at the local spots doing crazy shit that I never could have imagined.
Are there skaters you pay close attention to now? Who gets you stoked?
- There's so many! It's all so cool from the VANS video to the instagram videos of the homies.
Who or what were your early influences when you were first coming up?
-Jason Lee, Blind Video Days, Ban This, The Stereo Videos, and definitely Eastern Exposure.
Who would be on your list of top five favorite styles ever in skating?
- My top five of all time? Oh man just that natural outer-space-hello-style! You know, The Gonz, Guy Mariano, Mike Daher, Ray Barbie, even Heath. So many others too though.
What's in the works for you for the rest of the year and beyond?
- Let's stay on the good foot for the future and keep moving forward. For real, the last year has been a real humbling adventure in my life and I'm glad you guys have been apart of that and I'm glad to be apart of your adventure too.
No doubt, anything else before we sign off?
-For real, thank you skateboarding! Everything that goes with it is important in this fucked up boring place. Its our creative release and the way to take in this life. Way honored to have a guest wheel out with you guys with such a heavy team, and the Rick-O and Scott Kane guest joints too. Just very stoked to be apart of the fam' and to still be thought of to this day in skateboarding. That's the thick ties and bonds that skateboarding can create. Also, thanks to my daughter for helping get these answers across and all the typing back and forth. Peace