The landscape of skateboarding is constantly evolving, with young talents pushing boundaries and redefining what’s possible. Recently, we’ve witnessed this firsthand at San Francisco’s iconic Wallenberg, a spot once considered a career-defining challenge. Toby Ryan’s nollie backside flip and Dylan Jaeb’s fakie kickflip have sparked a debate: Is Wallenberg still the formidable beast it once was, or has a new generation of skaters rendered its reputation less intimidating? We spoke with Toby and Dylan to delve into their experiences, their thoughts on the spot’s hype, and the intricacies of tackling this legendary set of stairs.
Toby Ryan's nollie backside flip at Wallenberg
Wallenberg, since Mark Gonzalez’s groundbreaking ollie in “Video Days,” has been a proving ground for skateboarders, a place where signature tricks are cemented and limits are tested. It has been built up through the years, through contests, enders, and edits, as a formidable challenge, a dragon to be slayed. However, with Toby and Dylan’s recent achievements, the question arises: has the spot’s mystique diminished, or has the new generation simply raised the bar?
Were you surprised that an NBD down Wallenberg still carries so much significance in the skate community?
Toby: Definitely. It was all quite random. I kind of claimed it, so I felt like I had to follow through. Once I got there, it didn’t seem as crazy as I anticipated. I was hyped to land it, but it didn’t feel extraordinary. When you have a trick dialed, it’s not that big of a deal. I’ve certainly battled other tricks much longer. Though, I was training for it beforehand [laughs].
Dylan: It’s funny how that’s the main topic people bring up when they talk to me now. When you land it, it just feels like another trick; you’re just stoked you got something. None of my close friends skate big sets like that, so when I got home, it didn’t feel like anyone cared much, or that’s how it felt.
Having watched countless videos of Wallenberg, did skating it yourself live up to the hype?
Dylan: It was a mixed experience. It’s a long set of stairs, but the roll-in makes it clearable. The impact wasn’t as bad as I thought either, because of the speed. We watched videos of it on the way up, feeling very nervous about it, but when we arrived, it was just a stair set. There’s only so messed up it can be. Davis Gap would be far more insane. There are skaters like Chris Joslin, who frequently skate huge stairs, that wouldn’t think much of Wallenberg. They have skated spots way bigger and landed tricks on them.
“There are skaters out there, skaters like Chris Joslin who skate a lot of stairs, that Wallenberg wouldn’t be shit for.”
Toby: We were tripping out at first, thinking it was gnarly. Miles Silvas went back like ten times or so. The drive there was stressful, but it ended up being easier than we anticipated. I was there when Brandon Turner landed his switch hardflip, so I had a bit of knowledge of what it was like before committing to it. Still, when I got there, I thought, “Fuck.” It’s massive, but the roll-in makes it less intimidating. You just need to accept that you’re going to clip a few times.
Toby Ryan performing a trick at Wallenberg
Speaking of the roll-in, is that an essential part of the challenge, or does it make the trick easier?
Dylan: It’s so fast. Also, when you’re looking down at Wallenberg from the edge, it looks massive, but from the roof, it looks like an eight-stair. That angle makes it far less intimidating. Pushing in is gnarly, but in reality, it’s just a big stair set.
Toby: I agree, there’s no other way to do it. I wish you didn’t need it. It would be so much more badass to just bomb the hill without pumping. Pumping into a set is just weird [laughs].
How did the physical impact on your body compare to what you had expected?
Toby: The impact itself wasn’t so bad, but the speed makes the slams brutal. You’re rolling and ragdolling, similar to a car crash. My hand and hip were wrecked, the whole side of my body, but my feet were okay.
Dylan: It’s similar to jumping down a 10-stair multiple times. They recently repaved the landing, and the fresh asphalt stings badly. New asphalt has chemicals that burn differently than old asphalt. That night, we went back to the hotel and the burning sensation was so bad in the shower, we were like, “What the fuck is that?”
A GIF of Toby Ryan skating
Were you attempting an ender when you landed your tricks?
Dylan: No, Toby had already completed his video part and went there knowing his trick was going to be his ender.
Toby: Yes, I didn’t have anything else significant.
Dylan: I was simply skating with him. We would both have been too nervous to skate it alone, so I was there to support him and maybe give it a try. I had a part that I was planning on releasing on my YouTube channel, so I figured I’d use it as an ender for that. I wasn’t overthinking it [laughs]. Primitive was in the area because Filipe was attempting a trick on Clipper, so it all fell into place. Toby landed his nollie backside flip, and then we went to Clipper to watch Filipe heelflip back tail it. The next day, they came back to film because they had all the filmers in the area.
That’s insane, you were just going to post it on your personal YouTube channel?
Dylan: It was pretty random. I wasn’t expecting to do anything, I just wanted to skate it with my friends with no pressure, no filmers, just to feel safer. I hate dragging people out; it causes so much anxiety.
Dylan Jaeb at Wallenberg
I didn’t realize you guys didn’t land your tricks on the same day. Can you walk me through what happened?
Toby: When we first started skating, we were just ollieing, and Dylan broke his tail. He had to set up a new board, and I was already locked in on my trick.
Dylan: For some reason, it’s really hard for me to ollie stairs, and when I finally stuck one, I broke my board. By the time I had a new one, Toby was already landing his nollie backside flip. I didn’t even try a single fakie flip. I tried another ollie but he was sticking every attempt, so I let him have my tries. He ended up landing it, rolled away perfectly, and hugged Jim. It was great.
Toby: I landed it, and then the cops came and kicked us out, which is rare. Dylan was sticking it, but we had to pack the ramp back into the U-Haul. It’s such a chore to skate that spot. Dylan was like, “I’ll have to come back next week,” and I’m like, “Nah, we’ll just come back tomorrow.”
“Fakie flip is way more fucked, especially fakie to fakie.”
Dylan: The next morning, we returned to try again. The first day was windy and cold, and the second day was perfect, no wind, no clouds. Toby could have done it ten times easier in the conditions I had. I ended up trying for two hours, probably around 100 attempts. I couldn’t get my feet set up, you have to roll off the roof into the ramp. I could get my foot into a fakie ollie position but could never get my heel far enough to fakie flip. A lot of the attempts, I would just revert, run down the stairs, or miss my pop. Those attempts where you know you’re not going to land it right when you roll in, and you just have to jump down, are so draining.
Toby: He broke his board again that day, but otherwise, it was pretty chill. I think fakie flip is way more fucked, especially fakie to fakie.
Dylan: Yeah, I stuck one and my tail broke, and I hit my head. That stick was the one I felt like I was meant to do, so when it broke, I thought I’d have to return again. My friends helped me set up a new board quickly, it literally took two minutes. The new board felt stiffer, making it way easier, and the next attempt, I rolled away. I wheel-bit a little, and it didn’t feel like the best roll away, but I was done. It was a miracle that I made it.
A GIF of Dylan Jaeb skating
Dylan, why did you choose to fakie flip it, and did you consider that no one had done a fakie trick down it before?
Dylan: That trick is less scary for me to try down stairs. It’s easier to see, compared to a treflip where it’s hard to commit. With a fakie flip, it sticks to your feet, and you can choose to commit to it or not. It made me nervous because nobody had skated it fakie, but they had just redone the ramp for someone to skate it nollie, and they were clearing it really easily, so maybe the ramp was faster.
You two skate together often. Was there any competition regarding who would land their trick first?
Toby: Nah, he’s my close friend. We were just stoked to skate it together, not alone.
Dylan: Toby doesn’t think about that kind of stuff. We were just skating. I did see some comments asking if I was mad that he one-upped me. That’s not the kind of skating we enjoy watching or doing, so it’s hard to say.
A group photo of skaters at Wallenberg
Two NBDs at Wallenberg, what was the celebration like?
Toby: The night I landed it, I was so hyped but felt bad because Dylan was stressed. I was getting drunk [laughs]. Jim gave us the company card and told us, “Go get whatever!” We went to a sushi place, and I got the most expensive thing on the menu, a wagyu steak. I was hungover the next day at Wallenberg.
“Jim gave us the company card, and he was like, ‘Go get whatever!’”
I remember we went to Deluxe after, and Jim was so stoked. He was like, “Grab whatever for anything.” He walked me around the warehouse, “Get this, get that.” I got baby clothes [laughs]. Jim was like, “Hey, someone will have a baby.” We got so much stuff we had to wheel it out on a dolly. It was like those old Product Pillage videos.
Dylan: I was happy for Toby but so nervous for myself. That night I had a lot of anxiety, and I was really quiet. Everyone was stoked, and I was just sore thinking about skating the next day. It was a classic celebration meal. I’d never had anything like that. The night I landed it, we just drove home [laughs].
Would you ever attempt another trick at Wallenberg in the future?
Dylan: Maybe. I know everyone wants someone to switch treflip it. There’s a theory that Shane O’Neill had done it, and many people have tried, so that’s probably the only one really worth doing.
Toby: Realistically, probably not, but maybe just a straight nollie flip.
A GIF of Toby Ryan performing a trick
What’s your personal favorite trick to ever go down at that spot?
Toby: I’d go with the classic, Andrew Reynolds’ backside flip.
Dylan: That Reynolds backside flip, specifically the long lens rolling angle. That one resonates with me the most. Or Shane’s nollie backside heel. I used to watch that part a lot when I was a kid.
Out of all the legendary spots like Wallenberg, is there another spot of that caliber that you would want to skate?
Dylan: I’m not a huge fan of going to these spots to land NBDs, even though it’s cool to get your name in history, but that’s not really my goal. Carlsbad Gap would have been awesome to skate. We live close by, but I never got the chance.
Toby: I wish the Carlsbad Gap was still around. It’s like right next to my house.
Interviews by: Ben Komins
Photos by: Bailey Schreiner
