Thrasher Magazine

I remember watching Myles skate our local DIY spot for the first time when he was about 16. It looked like he was playing skateboarding. He landed every trick he tried within a few minutes, sat down for half an hour, then got back up and did the most mind-blowing gap—first try. Since that day, every time I roll with him I find myself skating less and watching him more because I don’t want to miss anything he may do on the first attempt. He was such a humble, cool kid and that hasn’t changed at all as he’s grown into a young adult. It’s amazing to see how much he’s progressed, and I don’t think he’s even begun to unlock his full potential. Myles has a strong hunger for skateboarding’s history and roots and keeps a good distance from the day-to-day machine we call social media. So don’t get bummed if he’s not quick to respond to your DM—he’s probably watching a copy of H-Street’s Hokus Pokus with his friends and taking notes. Baltimore loves you, Myles! —Gary Smith


Take a seat and watch Myles earn his pro stripes in Toy's newest

What’s your earliest memory of skateboarding?
Watching my brother and his friends out front.

Where did you grow up?
I grew up in Towson, Loch Raven area which is in Baltimore County. I’ve always been there.


So what did you skate around your house?
It was just the alley—that was as far as I could go. It started with myself and a couple of kids in the neighborhood. We would build stuff. Eventually my dad started hooking it up with ramps.

How were the ramps? My parents were terrible at it.
He has his own carpentry style, so he was pretty good at it. We would do it in the alleyway or sometimes in the basement. It was pretty small and had low ceilings but we would skate flat in there.

What were the first full-length videos you saw?
My first full video was from my neighbor Scott Everly. Shout out, Scott. He gave me Foundation’s Art Bars, Yeah Right!, a couple 411s and Sight Unseen.

Kinda strange that you grew up watching Tum Yeto. I’ve heard stories of you having Toy Machine posters on your wall. What made you like Toy Machine so much?
I was a little kid and had a bunch of things I would hold onto. But Toy Machine was the earliest thing. I think it was a mix of my friend Sam—every board he got was Toy Machine and I thought it was super sick. Growing up I missed out on Good & Evil and Suffer the Joy. I watched Jump off a Building, though.

Wallride nollie to 5-0, on trend LAMF    Photo: Aponte

I still think it’s so crazy you had theToy Machine posters on your wall when you were growing up. I’m telling you—no one gets to ride for the company they wanted to ride for. I wanted to ride for Girl. Girl was the best. I was on Media. No disrespect! I’m glad I still got the chance. But it’s pretty surreal.
It’s insane. Once I became aware of Brainwash, I was watching that video damn near every day.

If you could pick your favorite Toy Machine rider from any era, who would you choose?
That’s hard. I think initially it was Leo. I had a bunch of Leo posters. His demeanor and how he skated just struck me. He had a big influence on me early on. Even now, that all still holds up. But diving into more Toy stuff, I’m a big fan of Brian Anderson and Jordan Taylor. But all time would be Leo.

Ed’s gonna kick you off for not picking him. He’s my all-time favorite.
To see his art on the boards is what hit me before anything else.

Jordan and BA's influence shines through on this cutty wallie front blunt shove      Photo: Karpinski

I have an eight year old named Silas and he loves Toy Machine. His favorite Toy rider is Daniel Lutheran. It seems like you two are close. Would you say your friendship helped you get on Vans?
I’d say we’re pretty good friends. I’m not sure if he helped me get on Vans, but I would hope so!

I know when you first got on Toy Machine through Sinclair, you wanted to get on Emerica too.
Stay Gold and Brainwash.

Their branding worked! That’s awesome. When did you venture out of the suburbs of Baltimore? What was your first stop in the city?
I think probably in the Canton area or Fed Hill.

Shove it nose wheelie, catchin’ the curve     Photo: Aponte

Your parents seem very supportive of your skateboarding.
They drove me everywhere. Every day. After school. They drove me to Minneapolis. They took me to 3rd Lair. They were always driving and dropping us off wherever, just letting us wander.

How old were you?
I think when I was about 12 I was going out to the city more. My dad would drop me off and my mom would pick me up since she worked in the city. They got me whatever I needed—boards or whatever.

So you kept skating, but what about your brother? Did he keep skating? Was he a jerk? My older son is a complete jerk to my other son.
Matt was always including me. The older kids were always doing their thing, but Matt always let me tag along. He was filming me early on. I wish I could get that footage. He figured out pretty early on what he wanted to do—he realized he wanted to be a doctor and he is one now. He’s a doctor in New York.

I thought maybe you learned 360 flips before him and he thought, My brother’s better; I’m out!
He was a manny guy.

Bucky goes switch on vert, but Myles has it in the streets. Switch back lip

Do you remember the first time you were at The Ridge, the DIY spot by my house? That’s the reason I have a shop.
Yeah, the first time was in middle school. Me and one of my other friends had found out about it and my mom gave us a ride there. Eventually, my friends got their licenses and I would just jump in the car.

Who did you look up to in Baltimore besides your brother—or maybe even just skaters on the East Coast?
I have a little list: Sean Powderly, Tony Massey, Matt Bullinger, Ian Smith, Chris Mentlik, Tyler Thomas, Spencer Brown, Rodney Jones, Jake Rupp, everyone from Vú skateshop and The Ridge. I knew Bucky was from here, but he was already in the video games and vert skating. I think seeing a street skater from the zone was what I noticed.


I looked up to Bucky. I remember when vert skating died and he had to street skate. He was so fucking good at it. It looked amazing. You aren’t that into YouTube skating—you wanna sit back with the homies and pop the tape in.
Watching skating on a four-inch screen sucks. You gotta hold the case and see the art. You gotta watch it until it burns into your brain.

Guy Mariano is my all-time favorite skater and I did that with Mouse. Did you have any run ins while growing up and skating in Baltimore? There aren’t too many gangs but we do have high heroin rates.
I feel like I was lucky enough to not have any scary interactions. You see crazy shit, but nothing that would harm me. I think when we go downtown we have to respect the space. I understand that I’m fortunate enough to go back to the suburbs. There’s times when you’re skating and someone will let you know that it’s their block or their corner. No ifs, ands or buts, you have to respect that.

You come from a good family and your morals are great. You seem to have a good aura about you which is why people were so stoked when you went pro.
Thank you.

Four-inch screens suck, but 24-inch-wide banks are just fine, apparently    Photo: Aponte

Were you sponsored before you got on Toy Machine?
I got some hookups. I got Osiris’ when I was younger. A pair of Vox shoes here and there.

No boards, though?
No boards.

I think every time we ordered boards, we got you some Toy Machine boards. Do you remember that?
I remember being in the shop when you’d call for an order and you would always say, “We got this dude Myles who loves Toy so much!”

I think Danny Wallace sent your footage in.
It wasn’t until I was on the Vú shop team that I started to get stuff.


I grew up knowing Mike Sinclair. I would stay at his house in Raleigh. I remember him calling me and saying, “Hey, Gary, I’ve been keeping tabs on your boy Myles.” My boy Myles? This is like talent-scouting shit. I’ll never forget it. That’s probably when your life changed. I mean, you aren’t driving a Bentley, but you know what I mean.
Skateshops are the backbone of all this. They’re run by people who love skating and love the community. They hold events and help people out. Usually they are trying to push the love of skating over business. I feel like it’s community driven.

My job is to do that, and we all win. Take your team riders and get them out there—the city of Baltimore wins. We all come up.
It was also a second home. So many times I was just hanging out at Vú. Shops are important.

When did you move to Long Beach? Who’d you move out there with?
It was four-and-a-half years ago. I originally moved out there with Julian Heller, from Philly. We got a two-bedroom spot and eventually four other homies moved in. We had the skate house goin’.

What do you think of California? Do you have a favorite place there?
I think I like Long Beach more than anywhere else out West. But I do like the West Coast.

Ride-on back Smith, Charm City hits     Photo: Aponte

San Francisco was always my favorite. I could never afford to move there, though.
I’ve been on a couple of SF trips and they were amazing. It’s a whole different world.

It’s like the East Coast with hills; it’s fantastic. Do you feel like you’ve found home now? Do you have a California license? I never got one. The only thing I got was a Long Beach library card.
It does feel like home. I have a friend group, my daily routine and my girlfriend. But it does still feel temporary. I feel like I have plans to go elsewhere.

Would you ever move back to Baltimore, or somewhere else?
I’m into the idea of moving—wherever sounds sick and somewhere I could do the skate thing. Baltimore would be on the top of my list to move back, though.

That’s what I did—I moved to Philadelphia because there was a skate scene there. That’s what is so good about the East Coast—everything is so close.
That’s the feeling. You can drive for a couple of hours and the scenery feels different. Out West, personally, it feels different. When I go out, the scenery doesn’t change.

Do you live with your girlfriend? Who do you live with now?
We live in the same spot. The roommate situation has switched up. Now I live with Ryan Calandra and John Jones. They’re from Maryland as well. It’s not as much of a skate house anymore—it’s much more toned down.

You probably own a vacuum now.
Yep.

So your girlfriend, she’s from Huntington Beach?
Yeah, I met her about a year after being out there. It’s coming up on four years. My first real, long relationship.


And she skates?
Her dad skates and she used to roll around with him when she was younger. I think she had a bad spill and stepped away from it. Since we’ve been together she got back into it more. We’ll go out skating and she’s been dropping in, bustin’ shoves.

She told me she grew up near Ed Templeton, which is kind of crazy, right?
I think they’re neighbors, if not in the same neighborhood.

I know you’ve been home here and there, but I feel like this has been the longest you’ve been home since you left.
Yeah, usually it’s a quick trip, like five days or a week. I’m staying back with my parents right now, filling the house back up again.

They’re stoked. That was the hardest thing, to be away from my family. My birthday is on Christmas and I remember crying on Christmas because I had no one to spend it with. Did it feel lonely when you first moved out there?
Totally. I got hurt two weeks into living there. I landed on my toes funky and it worked its way up to my ankle. It was a process of three to four months. I couldn’t go out to skate or meet people. I was in a rut.

Court-date nosegrind, didn’t even wear a tie     Photo: Aponte

Did you break anything?
I’m not entirely sure. I went to a podiatrist and didn’t really get too many answers. I was just told to stay off of it for a while.

“Don’t skateboard ever again!”
In the beginning there were definitely some hard times. Eventually I found my friend group and got into a routine. I always miss back home, my family and my friends. But whenever we link up it’s right back into the same shit.

You have Andrew Real out there. You got him a job filming you at Toy Machine. That is so rad—you’re both from Baltimore living in Long Beach. So you’re gonna stay out there a while longer, yeah?
I think I still have some time. Maybe if I could get back here sooner, I would be down.

With the Internet now, you could really live anywhere. Back in the day, I had to move out to California because that’s where the industry was. People don’t even go to work anymore! Was it weird being out in California with COVID and shit?
Actually, at the beginning of COVID we were on a Yeto trip. We were driving from Long Beach to the East Coast. Right around Alabama or Texas is when we started hearing about the lockdowns. Every other part of the trip got canceled. We went straight to Atlanta and stayed with Dakota and his parents.

You were there for a few months, right?
Maybe two months or more? We were there with his parents and they took such great care of us.

Imagine—you could have been stuck in Texas without knowing anyone. You got lucky. So how did you get on RVCA?
I got in touch with Austin Stephens through Don Luong. That was a trip in itself. I’m a fan of Austin—the king of cool.

Front feeble past the diamond plate     Photo: Aponte

When you moved to Long Beach, were there any pros that you tripped out on? Seems like everyone lives in LB.
I remember my first time driving by Cherry and seeing the whole Yeto crew. This was even before I moved. That was a trip. I remember seeing Daewon at Portfolio Coffee.

I was skating this school in Costa Mesa. Marc Johnson was there and he was trying the most bananas tricks. I remember fanning out.
Especially at Cherry. I used to see Jon Dickson early in the morning when I was working at Fastenal. He would be walking his dog and we’d wave.

So you’ve got Toy Machine, RVCA, Ace trucks, Vans shoes—what else?
Bones. Shout out, Vern Laird. He started holding it down after Tampa Am one year.

Going the extra mile after an already lengthy rip, frontside 50-50 dropdown 5-0

How was the X-Games Real Street? Sinclair hooked that up for you, right?
Yeah! Sinclair was the one who lined that up.

You did a switch back noseblunt on a car. Whose car was that?
It was an older LB spot. I know the Deep Fried dudes skated it. It sat there for a while.

Switch backside NBS to regular on an East Coast-tour-stop staple      Photo: Aponte

Did anyone come out like, “Why are you skating my car?!”
Actually, one time this guy from the window above was like, “That’s my car and you guys are skating it! That’s cool!” I think it was just a beater. We wanted to throw something in there to try and make it different.

It seems like your choice of tricks and spots is setting you apart. I don’t want to make it sound like Toy Machine has a staple—a lot of big rails as we know—but it seems like you are skating way different these days. Where does that inspiration come from?
It comes from feelings and chasing feelings of what sounds fun.

Kickflip at just the right spot     Photo: Aponte

You are naturally talented. Were there any tricks that you could never do?
I feel like there’s a whole list.

I mean something that always hindered you. Tré flips were my kryptonite.
I feel like kickflips are the hardest and I never feel confident in the flick.

It’s a very emotional trick.
The basic kickflip. But it comes down to what sounds fun. For me, I think about how to best showcase the spot and the environment. Sometimes the spot is telling you what to do.


I feel like every spot in Long Beach has already been skated. You come back to the East Coast and you could be the first to rub brick at a spot. That’s a really good feeling.
Yeah, I think it’s also just coming up with something that is yours. It’s hard to be at a 20-year-old spot that Arto already fucked up. I’m just trying to play.

Is there anyone you are super hyped on recently?
Brian O’Dwyer, Jahmir Brown, Julian Lewis, Ryan Hamburg, Corey Glick, Breana Geering, Brian Powderly, Josh Ferguson, Kevin Liedtke.

The roads are rough, but the East Coast humidity can kill you. Switch nosegrind shortly before his pro surprise     Photo: Aponte

So you recently went pro after being on Toy Machine for about three years. I remember talking to Sinclair months in advance. It was very stressful. We got your boards and we didn’t even know what they were going to look like. Shoutout, Derm from Tum Yeto. He went as far as to Sharpie every single box that said “Myles Willard statue board” just in case someone saw. I remember talking to your mom and setting everything up. You had no idea you were going pro.
I had no damn clue.

All the Tum Yeto dudes were at your house on that trip and I thought they would tell. Obviously you would still be surprised, but you really had no idea?
I had no idea.

Surprise, surprise!     Photo: Aponte

That’s awesome. No one blew it.
I was even having thoughts like, That’s not even on their radar right now.

I think it’s a big deal, man. The way you went pro for a company you looked up to. I feel like there might have been 500 people at the park that day.
I saw so many faces I couldn’t believe what I was seeing.

My whole job was to make Myles cry, but in a good way. Your whole family came out.
My girlfriend came out; my brother flew in from New York; my Long Beach homies flew out for the weekend. It was insane.

Has it sunken in yet?
It still feels like a dream.

Lotta friends in Long Beach. Hold the door for the blunt slide pop out     Photo: Karpinski

Has your motivation changed? I know you’re working on a new Toy Machine video and you’re filming in Baltimore. Sinclair wanted you to be home.
I’m always trying to have Baltimore in any project. My motivation was definitely re-sparked, especially being back East. It has been refreshing. It helps having close homies. We’ve been at it every damn day.

Do you have a trick list?
No, I just have spots that I want to hit. I’m pretty bad about planning shit. That’s when the pressure gets too hard. But I want to come through for Toy and come through for Baltimore.

Riding high on his May 2019 cover     Photo: Karpinski

You will. I’m sure it will be amazing. I have your Thrasher cover here, which still trips me out. People knew who you were but not really. A Thrasher cover is the biggest thing you could ever do. You do a wallride off a roof onto this vent-fan thing. Did you have to go back to that spot multiple times?
I went back twice. It was in LA, not too far from LAX. Ben Karpinski had the spot.

This is not a spot, Myles, it’s a roof.
Well, Ben had the spot and he showed it to me. That’s where it started. I just had to figure it out. It was super scary. You’re on the roof next to the main road.

Homage to Matt B with a Bennett grind in Albuquerque      Photo: Arias

Did you need a ladder?
No, I would step on a cart and then someone would throw me my board. When you’re up there you can’t even see the awning. With each jump it would come off the wall a little bit. I hit a point where I couldn’t jump on it anymore. I broke a board and I didn’t bring a backup. So that was actually done on Don’s board. I think in the photo it was mine, but in the clip it was Don’s board.

Did you have a whole crew with you?
It was Don, Ben Karpinski and Braxton Powers. Braxton helped lay out some wood on the awning.

The back lip doesn't dip more than this     Photo: Aponte

Did the cover change you at all? Did more people know who you were after that?
I think it’s changed in some aspects. Personally, it gave me a feeling of accomplishment. I never could have fathomed getting on the cover. Especially these days, there are a bunch of badass photos. It gave me the feeling of what I always looked up to in pro skaters.

This one is from your mom—tell me about the first time you got high.
Well, I must have been like 17. That’s funny, just another time of her holding it down harder than I could ever imagine. I came home acting differently. I told her that I was freaking out a little bit. She didn’t scold me but she made me super comfortable. She made me some food, we had cookies and talked. Mom goes above and beyond.


Your parents are awesome people. Do you have any future plans?
I feel like now that I’m 25, I’m starting to think about my future, my body and what it needs. It’s hard to think too far. I’m thinking skating-wise and have skating goals, just trying to manage and put myself in a position where I’d want to be in the future—pushing off work for as long as possible but that will come back around, too. As of right now, I’m trying to stick with skating as long as possible. I’m thankful that I’m able to pay rent and live.

Do you want to close this with any words of advice for the kids?
Just have fun with it and remember why you started. Don’t stress out on Instagram and sponsors. Just go out and explore your town or city. Support your friends and your local shop. The rest will come.

Let Myles Willard live! Switch heel and welcome to the future      Photo: Karpinski