Not every skater has the good fortune of being born in the right city at the right time and falling into just the right crew to make it into the spotlight. But there are several dudes holding it down in their forgotten cities, shredding under the radar and inspiring those of us paying attention to the underground. Brett Weinstein is a prime example of one of those shredders, staying put with his local crew and making waves with their own independent projects. Waves strong enough for us to take notice here in NY and all the way in Montreal at Studio Skateboards. - Josh Stewart

Brett Weinstein NY City Hall / Photo: Josh Stewart

I guess it's mandatory for any interview to first ask how and when you got started with skateboarding?

Just the classic neighbor had a skateboard story. It was a Mongoose board haha, the same company that makes those funny bikes. I got my own first board when I was 9, It was a Dill Alien board. I picked it out not knowing anything about skating, but psyched that was my first choice.

When did you finally leave the burbs and move to Chicago?

So I moved to the city when I started College in 2013. I left school after 2 years and have been living there since.

What did you go to school for?

I was going to school for marketing at the University of Illinois at Chicago (UIC). Just wasn't for me, so I left in the hopes of going somewhere else but I just never got around to going back.

What've you done to survive and pay the bills since you first moved there

I've had all sorts of different jobs. For a while after I left school, I was dog walking during the day and would deliver cookies on my bike a couple nights a week. After that, I worked at a bank doing processing work for about a year. Once I started wanting to kill myself there, I left and went to Montreal for the summer. I just recently got a job in a warehouse for a logistics company, and that's going pretty well so far. A lot of unpacking boxes but the days go by really fast which is nice. - Damn, I was eating hot Cheetos and got some on my girl's laptop. She's gonna be bummed…

SPOT! Launch out of the bank to FS smith grind and into the second bank in St Louis. Photo: Stewart

You've got a pretty tight crew. Was it filming for the Deep Dish videos that brought all of you together in the beginning?

Pretty much. I've known some of the early members a lot longer than Deep Dish has been around, but really starting to skate and film a lot with everyone was how the first video came about and the ones proceeding. We're always going out skating with different people that move to or come visit the city. Personally, I'm pretty much down to go skate with anyone unless they're a big goofball.

OK, so you ride for a Canadian board brand, you're always traveling with the NY Theories crew, but you live in Chicago. How does all that work?

Well luckily, flying to NYC from Chicago is dirt cheap since they're both big hubs. Shout out to Spirit Airlines. People can hate but I get flights to New York for like $40 sometimes. They don't serve free drinks anymore though which is lame. Studio is based out of Montreal, so I'll go up there every so often and hang. I spent a month there this past summer, it was great. If I had to move out of Chicago, I'd go to Montreal. The meanest Canadian is equivalent to an average American.

Brett Weinstein: Ollie over to 50-50 down / Photo: Josh Stewart

When you're on a skate trip, which do you find more important, choices of skate spots or choices of restaurants?

That's really tough… If I'm going to a city I don't know much about, I'll definitely try to gain a knowledge of the food as much as the spots. I just like to eat good haha. I pretty much spend all my money on good food, and that's not just on trips, that's always.

What're the best restaurants you've been to on a trip, or what city has the best food?

Damn, best food city is tough. I mean, New York is 

obviously sick because you can get anything you want whenever; Sorry to be biased, but if you know where to eat good in Chicago, you can get any kind of food here done really well. Amazing Mexican, Indian, Italian... The list goes on. And obviously great pizza.

What's the best Deep Dish spot?

I think the best Deep Dish pizza spots are Peqoud's and Pizzeria Uno. But don't confuse Uno with the shitty Uno Chicago Grill chain because you'll be disappointed. I've recommended Uno to people from out of town before and they've accidentally gone to that bullshit chain and been so bummed haha. I'll get heat if I don't throw Lou Malnati's on the list. They kill it too, but #1 for me is Peqoud's for sure.

Theories ad from North Mag. Design by Pat Stiener. Photo by Stewart

I've noticed that when you stay on our couch in NY, or during road trips, you like to strip down to just some tiny, creepy shorts immediately after getting back from skating. That doesn't seem weird to you? Basically just being like an underwear model in the middle of the house with all my roommates walking around?

Haha Jesus. I just get warm super easily and like to be comfortable. Same reason I always skate shirtless. It's much more comfortable than sweating my ass off through a shirt in 10 minutes and being soaked for the day. Luckily you have an extra room at your house now for me to be a creep in.

Can you give us a brief rundown of the scene in Chicago lately? 

Well we're still doing our thing with Deep Dish. There are some sick skaters here, but a lot of them either just skate for fun, or skate like they're at The Berrics. If I had a dollar for every kid that tried to hardflip the stairs at the skate park I'd be doing pretty well for myself. But don't get me wrong, there are definitely exceptions and dudes that are sick here. I think there will be a point though where Chicago will start to get a bit blown out... Not looking forward to that.

Crook Transfer / Photo: Josh Stewart 

Who are the best skaters from Chicago, do you ever see Jub?

Jesse Neuhaus is my favorite skater from Chicago, but I think my favorite person to watch Chicago footage of would be Kalis. I've never seen Jub around haha but he's an obvious legend. I live right down the street from that thin step up ledge to drop he Ollied up then dropped off. That shits bonkers.

What skater, brand, video part has gotten you the most hyped lately?

That's such a hard question to pin down because of how much stuff comes out every 10 seconds.  I just watched that guy Jarne's pro part for Element and was surprised how much I liked it. Generally, I enjoy what I feel like most people would say nowadays: Palace clips, those Atlantic Drift edits, John Wilson's edits are cool, everything Grant does with WKND is awesome… Oh, really enjoyed the Traffic video. I could write a memoir with video clips that I watch.

If you could trade out Chase Plaza with any other skate spot in the world, would you do it and what spot would it be?

I wouldn't trade Chase for anything.

The Studio full length video premiered a few months ago and a new Deep Dish dropped pretty recently as well. What's next on the table for you? What're you working on now?

Well by the time this comes out, there will be a new Studio promo out.Probably a new Deep Dish clip as well. Other than that I'm not too sure, Josh. Why don't you tell me what we're working on??