chrome ball interview #130: jake rupp

Introduction by Josh Stewart

It’s difficult to look back on anything and understand the context and time in which it occurred.  Nostalgia is one thing, but to convey the impact that something or someone had in the era where they made their initial splash is nearly impossible.

After a nearly decade-long golden era started to come to an end, skateboarding in the late 1990’s had started banking hard to the right. During the tiny short span between 1990 and 1996, style and technical ability had merged seamlessly into such sublime manifestations as Mike Carroll, Gino Iannucci, Quim Cardona, Keenan Milton and an impressive list of similarly iconic styles that shaped our collective definition of style up to present day. But as 1997 and ’98 progressed, the X-Games reached its third year, Jamie Thomas had set off a new handrail craze with his Welcome to Hell part in ’96 and the 411-era was noticeably starting to take over. Limit-pushers began to take the steering wheel, pushing style and soul into the backseat as skate media began focusing almost entirely on the California scene. Although I enjoy all styles of skateboarding, I had started to become disenfranchised by this growing imbalance.

It was right around this moment that a frail kid from rural Maryland rolled onto the street course of the Skatepark of Tampa for Tampa Am 1998. I was there, as usual, dodging bullets on the course with my hi-8 camera in hand. And although the talent on the course that weekend was incredible, Jake Rupp just stood out like a sore thumb. And not just because of his scraggly pony bun. From my memory, Jake used one of his only 2 runs to just kick turn on every ramp and pump over the pyramid, not doing a single trick. That only intrigued me more. You can often study a skater’s style and figure out what scene he grew up in or what skaters he emulated as he developed. But Jake’s style was all his own, I had never seen anything like it and he immediately captured my imagination. After the contest, everyone crammed back into over-stuffed, stinky vehicles filled with sweaty used clothes and empty beer cans to drive back to their respective states. And I started trying to figure out how to get Jake Rupp’s phone number. Pre-internet age, this was still a difficult task. After a little bit of networking on my landline phone, I found myself cold-calling Jake out of the blue and asking him to film what would become the last part in the first Static video. Thank god he agreed.

Anyone who was around Jake during that era can attest to the electricity his skateboarding and personality emitted. I would say that in Jake, I discovered a large part of what I felt was missing in skateboarding at that time. In a shockingly-short 5-6 weeks of filming, Jake created a video part that is, 20 years later, still one of the best parts of the series and one of my own personally proudest creations. And the magic that his part added to the first Static video really helped to shape the identity and ethos of what the entire series would come to represent over the years. So I’m stoked to see his story captured in the digital time capsule of Chrome Ball so that others can hopefully get at least a small glimpse of how special this frail kid from rural Maryland really is, and, of course, the magic of the pony bun.


CBI: Before we get too deep into things, in doing my research for this one, do you consider yourself a rasta? Were you a rasta? How would you explain it?

Jake: Yeah, man, I was turned onto all that stuff as a teenager through listening to reggae music. It just really spoke to me. Beyond thinking that it sounded cool, I wanted to find out what it was that they were actually talking about. Just by listening, you start to learn things and piece it all together.

When you’re wylin’ out as a kid, I feel like it was something that gave me direction. It really influenced me to start paying attention to things like my health and conscious living.

So do you still consider yourself a rasta these days? Maybe more of a hippie-vibe, perhaps?

I'm kinda just everything, man. At 40-years-old, you just learn things over time, like the need to find a balance. Rasta Livity and the vibration has influenced me, in addition to other mystical, self-knowledge teachings.

I guess you could just say that I’m a natural mystic. I've always been a seeker of the greater workings... but at the same time, I think way too much and know nothing. (laughs)

You’re originally from Pennsylvania and moved out to a farm in Maryland, right?

Here’s the thing with that… You know the Mason-Dixon line? The line that separates Maryland and Pennsylvania? That actually goes through my property. I’ve lived on this same farm for the last 30 years but it’s all the same area. I’d go to school in Maryland but I also had stuff on the Pennsylvania side as well.

So how did you get into reggae and rasta out in the country? Is that a common thing out there?

(laughs) No, it’s mostly rednecks where I live. Deer hunters and big trucks. Bars built out of cinder blocks. We’ll probably hear a few gunshots out there as we do this interview.

We were total outcasts in the 90s. My younger brother and I, between us and our little crew, we were definitely outsiders. The hippie freaks.

I have to imagine some pretty gnarly run-ins with the townies.

Oh, for sure. The whole “skater fag” thing, making fun of us. And that was just the skater portion of it. We already weren’t cool and to add all our hippie stuff on top of it, they thought we were totally out there.

“Vegetarian!?! What the fuck is that? I eat steak and potatoes!”

“Well, I love you. And it’s a good thing to eat some vegetables.”

But as times have changed, it’s mellowed out a bit here. I’ll even eat some deer meat now, too. It’s all a balance.

Any particularly crazy encounters, though?

Just your typical stuff. Nothing really directed at the hippie-thing, more just because we were skaters.

Actually one time, Jon Mehring was out here, shooting photos with me at this little carwash we used to skate at. There were a bunch of rednecks that lived close by and as we were skating, I just happened to look over and they're all walking out of their garage, carrying shovels. Carhartt overall kits with shovels and a bunch of mean looks on their faces.

“We’re outta here, man. We get it.”

Jon and I combined are maybe 200 pounds. It seemed a little extreme.

The myth was that you grew up on a farm with a little mini-ramp inside your barn, almost Buster Halterman-style… is that really how it went?

Yeah, I actually had a couple of mini-ramps in my barn over the years. My brother and I had our own little program going in there. Because it’s so isolated out here. It’s a 10-minute drive to the nearest gas station. There’s a pizza place that will actually deliver out here now but even that was just within the last couple of years.

My brother and I were always 100% skate rats, we just happened to live out in the middle of nowhere. So those ramps in the barn were super important to us.

Is that the same barn that was in your Element ad years later, a frontside ollie with all those crazy lights?

Yeah, that’s the one. I skated that thing every day.

Was that lit or is that natural lighting?

That was all natural light, man. Just the sun coming through all the cracks on the side of the barn. We had a little lightbulb in there but I don’t think it was on.

The light coming through like that was just part of skating in there sometimes.

That had to be distracting!

(laughs) That’s an interesting take on it! But it wasn’t that bad. It’s not like it was blinding or anything.

If anything, it was all the dust in there that made it hard to skate. That’s what really sucked.

Where would you go to skate street?

My family owned a restaurant in the local town, about 20 minutes away. Hampstead, Maryland. It’s a nice little town with some shopping centers, parking lots, sidewalks… stuff to street skate. So that’s where we grew up skating street, whenever we could get a ride into town.

Baltimore is about 40 minutes away so once we got old enough, we started catching rides there with all the older skaters around town. Pat Smith is actually from my area and a good friend of mine. He was a little older and kinda took me under his wing. It was largely through him that I started going out to D.C. more.

So a mini ramp and a town 20 minutes away was enough to get you through those early years?

Exactly, and I was lucky to have those cities around me. Because that’s really how I was able to make an actual career out of it. I just loved skating, man. I was always out there, messing around... almost in a little bubble. Once I was finally able to get out to where skateboarding was really happening, I was so inspired.

What were your thoughts on the more popular spots in your area, like Pulaski? Because while you did have a few clips there over the years, it does seem fairly minimal, especially for how popular that spot was at the time.  

My crew would always skate the entire city of D.C… kinda like how Ricky and his crew would skate all of Philadelphia. We’d always stop by Pulaski for an hour or so, for sure. But we were more on that East Coast Urethane tip. Session everything.

I’m only asking because in the face of perfect Pulaski, you made a name for yourself skating some pretty crusty spots instead.

Yeah, I actually preferred that kinda stuff. Because it was all so awkward and unique. It really made things challenging. Just a different take, you know? The sketchier a spot is, the harder tricks become, so you really get a rush when you’re able to roll away.

I’m actually much closer to Baltimore, which is just how that city is. Baltimore is super crusty. And after skating there for so many years, it’s just something you learn. You gotta be able to adapt a little more to your actual environment and what’s really out there. It makes everything seem less like a skatepark.

I mean, Pulaski is awesome. It’s pretty much fucking perfect. I just wanted something a little different than that… plus, I’ll be completely honest with you, I suck at manuals. Sometimes I’ll bust out a switch nose manny but that’s about it. And I’ve never been much of a ledge skater, either. Don’t get me wrong, I love my nosegrinds and tailslides, but I just like to ollie shit. Pop over something and get a sick picture out of it. (laughs)

You were definitely known for having some serious pop, almost like a flexy-bendy type of style… do you even know what I’m talking about?

(laughs) Yeah, man. I feel like a lot of that came from getting into things like vegetarianism and veganism. Hearing about yoga and giving that shot.

“Oh man, I feel all super loose and crazy!”

It’s just stretching and breathing but it really does so much. Being light and feeling out your body. I still practice yoga to this day.

That was a big influence from Quim Cardona and Matt Field.

And that translated into your skating?

Definitely. Because that’s the whole thing, instead of going to Denny’s for some steak and greasy potatoes, how about a smoothie with some yoga instead? It matters, man.

What was Coffee Skateboards? I noticed them listed in your Transworld Check-Out. Was that just a homie company?

Good question.

Coffee Skateboards was in Maryland, just outside of D.C. The guy who ran it wasn’t really a skater, more of a money/business-type of guy, but he put together a sick little team of local rippers. Pat Smith, Steve Ball… It was super small but I was down. Just a board or two per month.

But no, my first sponsor was this company called Elite Skateboards, out of southern Florida. This kid Derek did it… nobody remembers that one unless you’re a Florida O.G. It was me, Scott Pazelt, and a few other guys. That was a long time ago.

So you were sending out sponsor-me tapes back then?

No, that just came about through going out and meeting different people.

Around ’96 or so, my crew and I started going down to Tampa Am every year, just to check things out. I don’t even think I entered the contest in the beginning. We just wanted to see what all was going on, so I hopped in a car and slept on a couple of sofas.

But even back home in Baltimore and D.C., I was starting to make connections through people. I met Serge Trudnowski and AJ Mazzu down at Love Park one day, they introduced me to Ryan Gee and Pete Thompson, who shot my Check-Out. Things just went from there.

How did you end up on Silverstar?

Do you remember Greg Harris? My getting on Silverstar was actually through him. We had become friends though skating Pulaski together. He was from that area.

Yeah, whatever happened to that dude? He ripped.

I think he’s a real estate agent in southern California these days.

But he knew all the Philly guys really well. Ricky, Serge and Matt Reason… Greg would go up there to skate a lot and after a while, he started inviting me to go along with him, which was awesome.

We’d always stay at Dan Wolfe’s apartment, even if Dan was out of town. And as a 16-year-old kid, fresh out of the farm, it felt so crazy to suddenly be in that mix. Because Eastern Exposure had already come out by then, so these guys were like superstars in my eyes. But I quickly found out in meeting them that they were just like me. We all just love skateboarding, and that’s what diffused it all for me. We’re all regular human beings.

So yeah, just by going out and skating with everyone, I got on Silverstar. Ricky was the one who actually brought it up to me one day while we were all out skating.

“This kid’s cool. What’s your address? We’re gonna start sending you stuff.”

It was actually a weird time for them because this was during that brief stint when they were still Illuminati, through Zoo York. And the first package I got was actually an Illuminati box. I came along right at the end of all that, which wasn’t very long anyway. But everything after that was Silverstar and East Coast Urethane.

Next thing you know, I’m calling Serge. He had a little skate house going and I crashed on their sofa for a while... 1919 Bainbridge. 

Would you be out with Ricky, Matt and Serge a lot?

For sure, though, I remember Matt Reason always being very elusive. He’d never be out there the same way you’d see Serge and Ricky all the time. Matt always seemed to be more of this mysterious character. But because Matt and AJ Mazzu were always tight, I got to tag along with him to Matt’s apartment one time. The only thing that sticks out for me is Matt eating granola and blueberries in a bowl of soy milk, in-between doing these huge bong hits. And his place was wild, man. All dark with these candles burning. I just remember thinking to myself, “Damn, Matt Reason… we’re doing it!”

I wanted that lifestyle! I want some granola and blueberries, too! (laughs)

I feel like you came out the gate strong with a ton of great photos… but I never really saw video of them. What was going on there? Were things possibly being held for a project?

I honestly don’t know, Eric. For whatever reason, throughout my career, I could always shoot a good picture.

Yeah, you really did have some amazing photos.

It actually took me a long time to figure out how to work that angle to its fullest extent. Because you obviously gotta have great footage but a nice photo has its merits, too.

Maybe I wasn’t as focused on getting video footage as much as I should’ve been? A lot of times, I was just going out with photographers for stuff, not really having a filmer. Because there really weren’t that many around after Dan Wolfe left.

I do remember a lot of that stuff being hit-it-and-quit-it style, too. One go and then you gotta get out of there.

But I’m not really sure, to be honest.

Did you not just like filming?

I had my moments where I liked the camera but it always felt weird. Because growing up, my brother and I skated the local shopping center parking lot for years. No cameras. To suddenly have a camera around felt different for me. It was fun but it did take some getting used to, if I ever got used to it.

I feel like kids nowadays grow up skating in front of cameras, where it was not at all common when I was growing up. Filming was its own thing.

I saw that a few years ago, you had almost 4 minutes of lost footage surface from this 97-98 era… like most of your early photos and ads. What was the story there?  

Yeah, Pit Crew somehow came across all that footage, years later. They’ve always been supporters of me so when they wanted to put it out, I appreciated that. The Lost Footage.

I feel like all that stuff had gotten stolen somehow and then was returned. I can’t remember exactly how it all went down, it’s a pretty convoluted story.

But to have all that stuff come out would’ve been huge for you back then. Like that giant gap to tailslide that was in your Silverstar ad? That footage is gnarly!

I think that’s actually the same gap Gonz ollied in a Real video a few years later. That’s what I’ve been told anyway. It’s in DC with one of those tight run-ups. Super sketchy. We loved skating stuff like that back then. We were always out looking for those types of spots.

How long did that take? Because that spot is sketchy, dude!

(laughs) It is pretty sketchy, man. It probably didn’t take too long, because I was never really into trying anything for very long back then. That was never any fun for me. I’d basically give it a few tries and either land or slam. I was never one of those guys out there, trying the same thing over and over again for an hour. That was probably within ten tries or so.

I feel like that clip came out in a weird Pit Crew video from back then. I’m not sure, I can never find it online. I was actually talking to a kid about it the other day and he gave me some directions, like, “Go here, then here, then here to find it.”

Okay… I could never find it.

One of my favorite photos of you, ollie over the rail into that super crusty bank in Philly for Slap. I can’t imagine you throwing too many tries down that thing.

Yeah, that rail really wasn’t that high to ollie over so it wasn’t too bad. Before I finally committed, I popped a couple over and would just kick ‘em out… which meant I had to run down that crusty old bank and try not to kill myself. Finally, I decided to land on one and ride through all that crap. Through the cobblestones.

Because if you look closely at that picture, it actually goes out into a little ditch and then you gotta go back up the other side.

Is there video of that?

There is video of that. I’m not entirely sure but I believe it went into this weird First Division Promo.

That Lost Part also had your Krux nosegrind down the Gold Rail, where it looks like you also lipslid and smith grinded it all in the same night. That was no joke back then.

Yeah, that was an awesome night. Because we just randomly showed up there, a quick hit at the Gold Rail as we skated around the city. The thing was, there just happened to be a Pulaski O.G. at the spot, Randy Corey, sitting solo on the ledge by the rail. I don’t know what he was doing… chilling, I guess. Vibing everybody. But I got so sparked on him sitting there that I just started going at it. Everything kept working out so I’d try something else and ended up with a nosegrind for an ad. Completely random.

On the topic of Krux, what were your thoughts on the hardcore East Coast industry view that Ricky and a lot of the other Silverstar guys held towards sponsors?  

I subscribed to all that when I was younger. And it was something that I did try to work towards throughout my career, largely due to Ricky’s influence. But honestly, once the East Coast Urethane thing fell apart, we all had to find our own path. Because suddenly, we didn’t have many options on the East Coast to choose from. I mean, Ricky went to New Deal. They’re not East Coast.

I definitely tried to keep that East Coast Pride alive. I think we all did. But you have to be realistic with things, too. You gotta find the opportunities where you can. 

That’s how I found myself on Krux and even Creature for a hot second, before they went under and they put me on Santa Cruz. I just happened to be on a cross-country roadtrip from Tampa to Santa Cruz with Chet Childress at the time. I told him about Silverstar collapsing and he got all hyped on the idea of me riding for NHS… I didn’t even know what was going on. I never thought about the business of skateboarding in that way.

What did happen to Silverstar?   

The dude at East Coast Urethane was just so shady. I feel like there were rumblings almost immediately after Silverstar began. Politics where the owner no longer wanted certain people involved. They wanted to reorganize, but all of a sudden, there was no money. I guess he gambled it all away… that’s what I heard anyway. That was always the rumor.

It was rough because we’d see our friends who rode for other companies making all this money. The industry was starting to take off and we really weren’t seeing any of that. East Coast Urethane was an amazing idea and it should’ve worked, it just didn’t. And then it all fell apart. 

How’d you find out?

I was in San Francisco and got a call from Serge.

“If you have any other offers, you should definitely take them because this isn’t working out.”

I actually remember calling up Toy Machine. I found their phone number in an ad and just called them up, like, “Is Jamie Thomas there?” (laughs)

That’s amazing.

That’s how little I knew about how the industry worked. Because I knew Jamie was doing big things and I’d probably met him at a trade show or something. I think he told me to hit him up sometime and I took it to heart.

What kept you on the East Coast throughout your career? Why not move out closer to your sponsors? And do you feel like that possibly held you back at all?

Oh, for sure, man. Out of sight, out of mind, right? If you’re not in that mix, it’s easy to get lost in the shuffle. But I’m just a homebody. I like being in my comfort zone. It’s safe. I like traveling, for sure, but I also like being at home with my family. And as the years go on, you develop deeper relationships and start having kids. You get more and more tied to a place.

Maybe we’re just weirdos, out here in isolation? Because there were a handful of guys around here who seemed to be on the verge of something at one point. Back in those days, everyone would just go out to California for a few weeks and stack a bunch of coverage real quick. That’s basically what we would live off of after going back home. I’m a good example of that. That’s exactly what I did for years… looking back on it, maybe that just wasn’t enough. 

I’ve read you using the term “Hollywood Illusions” in an interview. What did you mean by that?

(laughs) Holy shit.

LA is just such a different world than where I’m from. Maybe I had too much of that East Coast hard edge about things, but LA, in particular, used to really trip me out.

I’d have to look at the context but off the top of my head, I always thought it was funny how attractive news reporters were in California. Like, if I watched the news, it was crazy to me that all the reporters looked like superstars. But they’re doing the news… I mean, it’s the news!?!

(laughs) So what Josh Stewart has gone on to call the quintessential Static part that set the tone for all the others, how did you get involved with Static 1?

I met Josh Stewart by going down to Tampa through the years. The Tampa guys were always so welcoming and super cool, which led to my making a lot of friends down there.

By that point, Josh had already done the Cigar City video, which I thought was really good. So yeah, I was familiar with his work. But he just ended up calling me one day about this project he was working on.

“Hey, I’m taking a road trip from D.C. to California and I want you to go with me. Two weeks of filming for this project I’m doing. What do you think?”

I just felt honored to be asked. And that was it. I didn’t film very long for that part at all.

He said that you filmed your entire part in two trips, is that right?

Yeah, there was that first DC-to-Cali trip and we did a second one, too, around Philly and DC. I just happened to be on fire at that time.

I want to say that my first trip for Static was towards the end of their filming for it. Because they’d actually been working on it for a while before I got into the mix. That DC-Cali trip was like their one last push to get footage from everybody. Josh was already working on parts for each of those guys, he just invited me along to maybe get a clip or two as a cameo. I wasn’t supposed to have a part originally. But things happened to work out where I accumulated so much on that first trip, me having a part suddenly became an option.

That’s why my part was at the end.

So that first Static trip you went on cross-county was with everybody…

Yeah, the DC to Cali trip was with the whole crew. Meinholz, Selego, Steve Brandi… Sean Mullendore was on it for a second but then he got weird and bailed, which was awesome. Classic, dealing with a bunch of psychos.

(laughs) What do you mean?

We were just being crazy. Skating and getting wild. That was just how we were living and Sean wanted no part of it. (laughs)

But Sean was such a good skateboarder, man. He could ollie anything.

Whatever happened to Mullendore? He was incredible.

He lives around here, in Maryland. I’ve heard that he works on high-end racecars. Like, the super crazy ones in sterile garages.

I haven’t seen him in forever but I did hear a story a while back about him walking out of a bar in Baltimore with the homies, having a good time. Evidently, he ended up grabbing somebody’s board and did a tre bomb in the parking lot, first-try. That’s Mullendore for you.

What was the overall feeling out there on the road, working on this little project for a largely unknown upstart? Did you have any idea it would blow up the way it did?

Not at all. It was just a fun project to work on with Josh and the homies.

I still remember meeting Josh and everyone in D.C. as we were about to embark on that trip. It was so exciting. I loved showing those guys all of the different spots around town… all those weird random street spots that are in the video. Everyone was so good and right away, I knew this was going to be a great trip and an awesome video. Like Ed Selego at the Gold Rail? That was awesome! You couldn’t help but get sparked after watching that go down.

The whole project just felt so natural. Being around like-minded people and vibing off each other, we quickly became a crew.

Of course, we have to talk about that bank-to-rail front nose.

Yeah, that was in Las Vegas, right there on the strip. It was, like, 100 degrees that day, so I was definitely rolling solo on that one. And that spot was super sketchy with a ton of security guards around. A definite bust, but we were able to eek out around a half-hour or so.

I remember doing a few ollies on it at first, trying to get the feel of it. The frontside nose just kinda happened. It was all real spontaneous... most of my skating was like that back then. Fortunately, that noseslide is just a little piece of magic that’s now documented forever.

But yeah, it was just a couple of tries. I actually hit my wheels on the rail as I was coming down, which always bummed me out a little. You can see it if you look closely at the footage. But the way Josh put all that together in the edit, it was awesome. Josh’s vision of skateboarding is incredible.

Wasn’t it Figgy who nosegrinded that in recent years? I loved seeing that.

Did you know Josh was going put your part after the credits like he did?

I’ve never been sure on what exactly his reasoning was for that. But that’s actually my friend jumping his dirtbike when it starts to glitch before my part. I always thought that was cool.

I liked being after the credits. I wouldn’t have wanted it any other way.

“Hey, this weird dude from some barn has a part in the credits.”

I love that.

Weren’t you supposed to get on Habitat around this time?

For a hot minute, Joe Castrucci was talking to me after Silverstar ended. Habitat hadn’t quite launched yet but I did get a box around that time, which was probably some of the first Habitat boards ever printed. But I’m still not sure what all happened with that. Because I thought that I was supposed to be one of the guys in the original line-up... but I guess they were already set on the crew that they would eventually go with, moving Fred Gall over from Alien and all that.

But Joe was always super cool to me. I remember him always wanting me to do this and that, trying to get into the mix. It was just such a tight crew. They were all set in their Alien Workshop thing, where I feel like I was more of an outsider.

That’s such a bummer, man.

Yeah, I gotta admit there is part of me that wonders if things might’ve worked out a little differently for my career had I been a part of that.

Was this ever revisited later? Being close with Selego and let’s face it, you and Guru have very similar aesthetics.

Yeah, but by the time Ed and Guru got in there, I was already over at Element, super deep. So no, it was never revisited.

Why Element? And did you have any other offers?

If I did have other offers, I honestly can’t remember them because the Element one blew me away. Because I’d known Donny Barley a little, just from being on the East Coast, but I never expected him to cold-call me one day, out of the blue.

“I want you to ride for Element.”

This is back when Element still had that classic late 90’s crew of East Coast powerhouse dudes. So I was down. They flew me out to San Diego the next week so I could hang out with everyone, just to make sure. And that was it, I was in.  

I remember sharing a hotel room with Billy Pepper and Kenny Hughes, which was pretty crazy. (laughs)

I love the thought of you three hanging out together.

(laughs) Yeah, I always got such a kick out of going on tours with those guys, in particular, because I’m sure we looked so crazy together. Me with my long hippie hair, Kenny Hughes being a gigantic black man and little Billy Pepper, who’s maybe 5-feet tall, out there running his mouth. Imagine the three of us showing up at your shop together for a demo?

“We’re here! We’re Element!” (laughs)

I remember one time in Australia, we all went to this crazy house party and Kenny ended up putting his hand through a window. I can’t remember why exactly, but he was all fired up over something. He cut his hand to shreds so we all had to take him to the Emergency Room.

So picture big ol’ Kenny, sitting on a bed in the ER, asking us to sneak him in some beers.

“Of course we’ll sneak you beers, Kenny!”

So yeah, there he is, drinking Cooper’s in the Emergency Room with a busted-up bloody hand. (laughs)

It seems so epic now, but at the time, that’s just where we were at.

How was riding for Element during the Bam years with all that money around?

It was weird, man. Because all of the trips seemed to get more and more elaborate. Doing cool shit and traveling the world, staying in these super fancy hotels. Bam’s board was obviously selling a lot, which seemed to be helping out all of our sales. I was making some pretty good money at that time.

But Bam always seemed like he was on his own tour, within our tour. A lot of times, he’d be staying a different hotel. Maybe he was going on David Letterman that night? That was a real thing. Meanwhile, the rest of us are either skating flatground down in the parking lot or at the hotel bar.

There would be literally thousands of people at every demo, but almost all of them would only be there for Bam… Bam or Mike V. And it got to be kinda hard after a while. I’d typically just go out, ollie some shit and call it good. But I gotta say, it was always awesome to watch Mike at those things. He’d be burning down the course at every demo. I guess my approach was a little more subtle.

That’s back when he was Fightin’ Mike, too.

Yeah, but he was always cool to us. He was actually pretty mellow about most stuff… like us smoking weed in the van? He didn’t care about any of that.

I don’t think I saw him get into a single fight back then, either.

Around this time, you had a Slap interview that went pretty deep into mysticism with some pretty wild, obviously written answers. What’s the story with that one?

Yeah, that interview tripped some people out, for sure.

My brother has a degree in philosophy and is super into Eastern religions and mysticism. He’s the one who actually conducted that interview with me and we worked pretty hard on those answers. I still remember that day, sitting out on my porch with him. We were just in that world of searching for deeper answers about things. Deeper reasoning…

Right, but I honestly read that piece in prepping for this and wasn’t sure if you actually talked that way…

(laughs) You know when you’ve just gotten turned onto something new and you start thinking about things that you’ve never really thought about before? I feel like that’s essentially what was going on there. When you have that kind of enthusiasm, you can go pretty deep into things.

I‘ve mellowed out a bit with that kinda stuff but I think that I’ll always be searching on that tip.

“In a cloud of smoke, evil spirits ran and vampires were dispelled. Then a set of skateboard wheels appeared and the evolution of a brighter tomorrow began.”

(laughs) Good one.

Yeah, that was about the Sartori Movement. Basically what I’m talking about there is skateboarding being a good outlet for me. Just a funny way of saying it, I guess. Using some mystic terms that we’d learned from a few books.

But yeah, because of skateboarding, I was free and in the moment. No longer trapped inside my mind.

So you’re just having fun with this?

Yeah, it’s not meant to be taken entirely serious. We just wanted to do something a little different. Having fun but at the same time, maybe turning some people on to a different way of thinking, too.

Was it difficult being a Buffalo Soldier while riding for this increasingly corporate, big money operation? Do you feel like they ever tried to change you at all for the sake of marketing?

I don’t know if “change” is the right word but they definitely picked up on my whole lifestyle, which quickly became how they started to market me going forward.

I feel like I just got increasingly lost in that whole world, man. Because it was all so different from how I'd been living just a few years earlier. It used to be that I’d just crash on a couch at some skate house and do my thing. Now, for all of my trips out to California, they were putting me up at these nice hotels in Ocean Beach or Huntington. Everything became so business-oriented after a while.

“We’ll pick you up at 2 for the photo shoot. This ad will part of a new campaign we’re launching, blah, blah, blah.”

It felt more marketing than skating at that point. Because of all that money floating around. So much money. And I feel like I lost a bit of my identity in all of that. Aspects of who I am and where I come from. I left a part of me back in those fancy hotels. 

How so?

I got complacent.

“Oh, this is all we have to do today? Go to this demo and then we can party in the Winnebago for the rest of the day? Awesome!”

That became the reality. It wasn’t about hitting that sick bank spot down the street anymore. I was getting lost in some bad stuff. It’s a common story.

I got a little too comfortable with things and then, all of a sudden, they couldn’t support me anymore. Because you’re not gonna get paid just to hang out for very long.

Is that interview you starting to become unhappy at Element?

No, that was still early on in my days at Element. I was still happy at that point. They hadn’t become part of Billabong yet.

That’s when things went south... Billabong?

Yeah, everything felt pretty different after that.

Billabong is an Australian corporation so, all of a sudden, there were all these Australian connections there… which isn’t necessarily a bad thing, just different. But like I said, everything was moving in this super corporate direction. Most of the guys who were on the team when I got on were no longer there. It didn't feel like my place anymore. It had run its course.

I realize that must’ve been a pretty healthy paycheck to walk away from, especially after joining their shoe program, but did you ever look around at all for other sponsors?

At that point, my daughter was my biggest concern. I felt like I couldn’t leave because I had to make money, which meant riding for Element. It was just all too big, man.

Is it true that Element made you quit IPath for their short-lived Element shoes program?

Element had some really big shoe plans at the time and they did push a lot of incentives my way in order to get me to ride for it. So while they didn't make me quit IPath, they were still able to get me to ride for them. (laughs) 

But on the other side of things, I was already feeling out of the loop with IPath. It was an awesome ride but once again, I felt like I was out of sight, out of mind with those guys. IPath was amazing and I was very proud to have been in that mix... unfortunately, Element shoes just didn't last too long. 

People always talk about the “Element Blackhole”… is that a real thing or do you feel like your own mistakes are more to blame with what ultimately happened there? 

No, my Element time with Kingman was incredible. He always was and probably still is one of my biggest supporters. I always felt like he believed in me.

He’s the best.

Yeah, he is. Dewitt came aboard around that time as well and both of those dudes had my back. So, in that respect, I can’t blame Element. I’m thankful for Johnny for including me on his adventures in skateboarding, traveling the world.

I just wasn’t living up to my end of the bargain. I wasn’t skating as much anymore... not as much as a professional skateboarder should. I wasn’t doing all that I needed to be doing for them as a company.

Why give so much footage to Pit Crew’s Where I’m From and not Elementality, leading to a shared part in your main sponsor’s video that came out around the same time? 

I’ll be honest, when Elementality Vol. 1 came out and I had a shared part with Tosh, I was surprised. Because I didn’t even think I had that much footage for it. Because I’m in Maryland, man. When I go out filming, it’s with Mark Nickels. He’s working on the Pit Crew video… so that’s where my footage went. The Pit Crew Video. That’s just how it worked out.

I definitely could’ve been more productive and goal-oriented with things. More focused. I just never took filming seriously. It was never a goal of mine to film some crazy part. I always hear people talk about filming video parts, that was never my priority.

But that nollie over the bar at Besos in Barcelona is still insane.

Yeah, that one was a struggle. Because it was so hard to hit my nose right on that round bump! I know that my front foot is flapping but I’m okay with that. I’m just happy to have landed it! (laughs)

I just remember Vern Laid being there, hyping me up to do it. He really wanted me to get it, which was awesome.

So I know that you were on Creation for a split-second before stepping away from the industry… what all was going on with you at this time?

Yeah, because I had been so heavily involved with Sartori Wheels, basically riding for them from the jump, they gave me a chance to ride for their board brand, Creation Skateboards. But that was short-lived. I will always be thankful for their support but I was just too far gone by then. 

I was just partying too much, man. I was drinking heavily, which led to depression. Boozing led to me isolating myself for a long time… for years. Because I was heading that way anyway, but after I was done with having sponsors and all that, I fell into a very dark period in my life. I still skated a little but I just wanted to be alone. No social media, years after everyone else was on it. And that was on purpose. I didn’t want to talk to anyone.  

It all fed into itself, man. My partying led to isolation, which led to more drinking. It was terrible. I remember seeing those commercials about depression on tv at the time, but it’s never that black-and-white. Yes, it registers. I know I’m depressed. Sitting there watching “16 and Pregnant” on MTV, like, what the fuck am I doing with my life? But it’s not like you have this big dramatic moment all of a sudden, like in the movies. It’s a heavy weight that you experience on all of these different levels. It manifests itself in literally everything you do and in all the relationships you have. It’s rough.

But I’m proud to say that 10 years later, I am doing much better. I am far healthier now at age 40 than I ever was at 30. Yeah, it’s sad to look back on all that stuff now but I was able to make it through and that’s awesome.

That’s great to hear, man. Happy for you.  

Thank you, Eric. I’ve been off the sauce for a while now. I’m proud to say that I’m clear-headed these days.

I have to imagine you being pretty bitter about things for a while…

Oh, I was pissed, man. I blamed everything on Element.

“This is all their fault. They suck, blah blah blah…”

That’s what I told myself.

You sound so healthy now. How’d you turn that mindset around?

Well, after trying to drown it all out with booze, which didn’t work, I was forced to take a hard look at myself and build my life back up. Because it’s always easier to blame everyone else, just to make yourself feel better.

At the end of the day, I can now admit to myself that it was largely my fault. I wasn’t a team player, which is an odd thing to say in skateboarding, but in my case, it’s the truth. Towards the end, I didn’t give a shit about demos or representing the brand. And you can’t be like that and expect to be around for very long.

It’s all a part of my story.

I know you’ve had a few guest boards over the years, that has to make you feel good.

Yeah, Magenta actually hit me up when I was in the absolute thick of my isolation, which to have something like that happen at that time, totally unexpected, really helped me out a lot. And I’ll be honest, I’d been out of the mix with everything for so long that it took me a minute to figure out what kind of an honor that really was. It was such a great thing. I feel like that might’ve been one of the things that helped drag me out of everything else I had going on…

And if that wasn’t enough, I had another guest board on Killing Floor a few years later. Another awesome thing for skateboarding to have given me. Shout out to John at Killing Floor for keeping me rolling.

I’ve seen a few recent clips of yours on Instagram, you’re ripping!

I’ve reconnected, man! Once I finally figured some things out, 10 years later, I was able to get back out there and let myself have fun with it again. It really takes me back to that special place… that special feeling we all get from skating that keeps us rolling.

Do you remember Gary Smith?

He rode for Media, right?

Yeah, Gary’s always been a big supporter of mine. He saw that I was out there skating and still doing good, so he asked me to ride for his shop, VU Skateshop in Baltimore. So I have a little home there now, which is awesome and really means so much to me.  

Honestly, I’m just stoked on being a skate rat again. I have a skatepark close by and I’m trying to get out there every chance I get. I’ll let the kids have all the crusty spots, I’ll be at the park. (laughs)

Sick. And you’re still on the farm?

(laughs) Yeah, still on that same farm, man! It’s nice out here. It’s springtime!  

Is the ramp still there?

It’s still here but it’s more of a skeleton these days. It needs a new layer of wood, for sure.

So what do you do out there in Hampstead, Maryland?

Well, with my family owning a restaurant in town for the last 50 years, I basically grew up in the food industry. Working in the kitchen or whatever. We sold the big restaurant a few years ago and now we just have a little café going. It’s my mom, my brother and I. My brother’s an artisanal-style baker, making Old World-style breads, while I’m in the back, cooking in the kitchen. It’s a lot of fun.

Your brother sounds like a super interesting dude! What’s the name of the café?

(laughs) My mom’s name is Mary Joe and it’s her place. MJ’s Café and Bakery. Stop on by.

Looking forward to it. So as we wrap this up, what would you say is the proudest moment and biggest regret of your skateboarding career?  

I was really proud of that Static video, man. That was probably my proudest moment, to be honest. Because the whole thing was just so pure. It came easy and felt so natural to do. Working with Josh, I feel like that was supposed to happen. My having a video part like that couldn't have happened any other way… and it basically never did happen again, really. But it wasn’t some corporate thing. Just my crew and I out there skating, working on this thing.

As far as regret goes, I feel like I did leave a bit of my heart in San Francisco but it’s all a part of my story and how I got to where I am now. So on a lighter note, I honestly regret not eating more food on all those international trips! Being vegetarian at the time, I really missed out on some amazing food! No prosciutto in Barcelona? Or even being in Thailand and not sampling some exotic fish in a curry? I really blew it, man. I should’ve taken better advantage of all those culinary opportunities! Not that I didn’t eat good, because I did. But now that I’m not so much of a vegetarian anymore, I wish I could get some do-overs on a few of those meals… instead of that baguette with cheese I probably ended up going with. (laughs)

Big Thanks to Jake, Josh Stewart and Isaac Randozzi. 


Anonymous said...

Jah Bless!

Anonymous said...

Honesty in this! Congrats Jake, keep it moving in a positive direction.

Anonymous said...

Super insipiring! Keep killing it Jake

Willem Dirks said...

such a good read, cheers chops and jake. that 180 photo at universitat (BCN) is one of my favourite photos. keep it up

Anonymous said...

Jake the Snake! I love you homie! Keep on keepin on!

Anonymous said...

Thanks to Jake and Chops both for this! One of the all time east coast greats. Awesome read.

Andrew H said...

Great article, I met Jake when he was 11 skating in his mother's restaurant parking lot. So much talent and it was always a pleasure to watch him skate!

Bari said...

that backside ollie hooooooooly sht,i need to get back into yoga lol, great interview tho perfect end to my thor's day, u def deserve to bein a printed

DLTDA said...

Such a rad and thoughtful guy. I love the maturation in his perspective. Big ups, Jake (and Chops)!

Anonymous said...

Hey it’s Brent Marks! The old birdhouse guy. I’ve seen my name pop up a couple times in these interviews, I’m stoked I’m kinda still remembered. I’m still skating a lot, and still doing triple flips. Cheers!

Unknown said...

Hey Rupp! Jake and the baltimore heads from pit crew would stay at my place a few times during Tampa am in 97 I think...Gary Smith was there...filmed a clip of a front feeble he did that was in my video in 1996 "adventures in hi8"....still keep in touch! Congratulations homie

Ashlee Rolfson said...

I recently read your blog post featuring an interview with Jake Rupp, and I must say, it was an insightful and engaging read. Your dedication to showcasing the stories and experiences of talented individuals in the skateboarding community is truly commendable.
stan lee net worth

Jennyfer Kreiger said...

The interview with Jake Rupp provided a fascinating glimpse into his journey as a skateboarder and his perspective on the industry. It's inspiring to hear about his passion for skateboarding and his dedication to pushing the boundaries of the sport.
does chime show pending deposits

Jennifer Walsh said...

The Chrome Ball Interview #130 with Jake Rupp is an intriguing dive into skateboarding culture and talent. While we explore Jake's journey, I can't help but wonder, #How Old Is Dolores in Encanto? Your blog offers a fascinating perspective on the skateboarding world and the people who shape it. Thanks for sharing this captivating interview!

Maria Adam said...

I appreciate your commitment to providing well-researched and informative blog posts. Your dedication is truly admirable.vickie lynn swayze

Maria Adam said...

Your blog has become a trusted companion in my quest for knowledge. Thank you for being a source of wisdom and enlightenment.vickie lynn swayze

Jennifer Walsh said...

Jake Rupp's interview reminds me of the intriguing character development in "How Old Is Dolores in Encanto," just like Dolores who adds depth to the story. Rupp's insights are equally captivating. #HowOldIsDoloresinEncanto