Interview conducted by The Editors
Harry Reynolds on Burnout, Balance, and Filming Uprise’s New Video
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Photo by Hunter Brown
Editors: What gets you excited to film?
Harry: Watching a skate video or movie, drinking just enough coffee, and having a good crew lined up.
Do you lean more towards planning-things-out out or going-with-the-flow?
To be honest, I prefer to go-with-the-flow because it opens up the possibilities. It can be for better or worse but leans towards being better more often. I think that the majority of tricks in the video were done without the intention of doing anything.
Although, a good amount of skaters in the video had a premeditative approach. Their focus helped lower stress, which isn't to say there wasn’t pressure. Sticking to a plan tends to develop expectations, raising the stake enough for it to become stressful, albeit necessary with a larger video like this.
Are there any spots you’re low-key tired of seeing in videos?
Wallenberg took a beating this year. Maybe we ought to give it a rest. Chicago specific, there isn’t one that I can think of. Since we’ve lost a lot of spots over the years, I want to see as much as I can.
Is there a Chicago skate spot that you feel people don’t get right on camera?
Nah, no way. There’s been so much footage from different skaters and filmers—local and foreign—at these spots that makes it impossible for me to say yes.
With that said, if filmers worked together on videos they’d be able to offer more perspective. Lots of times I see a video and think, “this could have used another angle” or “I wonder what the context around the trick is.” I’m not saying that to criticize the filmer but I think perspective is important. It’s a big task for any one filmer to capture a trick along with everything else that happened around it.

Photo by Hunter Brown
When did Uprise approach you to film and what was that line of communication like?
Uprise approached me to “Where You Been” in February, 2023 with the initial idea to film the younger generation. If I’m being honest, communication was an obstacle for everyone involved. I wish there had been more from everyone, including myself. Even so, the experience taught me a lot about working alongside different energies and the product of that is a video that will stand out in the shop’s legacy. I think that’s all anyone can ask for.
Does the video feel like something you drove creatively, or was it more collaborative?
I took it upon myself to take as much creative freedom as possible. Uprise was pretty good about meeting me halfway on my ideas, though I stood by my choices pretty firmly. I felt it was necessary seeing that the video took up a large part of my life. Looking back, I think we worked well together.
In terms of collaboration, I tried to work with local filmers, which felt like pulling teeth for the first year, haha. I really wanted more Chicago filmers to come together on this project. Though, I understand everyone has different priorities, which I respect. A good chunk of people did end up contributing, and I am thankful for that! It helped the video feel more communal, rather than one guy filming a lot of people.
When it came to showing everyone their edit, I felt that it was necessary. It was a window into what people’s tastes and visions were and I found a way to incorporate them on most things. Not sure if I’ll do that again or how I will do it in the future but it was nice to learn how to work with people that I hadn’t made videos with before.
Were there any visual choices in this project that you felt strongly about?
I had the vision of making the city look vibrant while adding obscurity into the b-roll. I knew that including landmarks like the Marina Towers, Calder Flamingo, and Chicago Tribune were safe bets, but I was aware of the fatigue in seeing those things. Some landmarks will always look good on camera, and maybe we can’t escape them, but I wanted a challenge. Using a prism filter created a ghosting effect that let me manipulate the image in ways that yielded a level of abstraction still easy on the eyes. Obscuring the city became a way to maneuver around tropes.
In terms of color theory, Chicago can look a little bleak so I wanted the colors to appear more rich, vibrant; closer to something cinematic.
Did you lean towards making Chicago feel more raw or polished?
There’s a sweet spot between those two that I strived for. I made it a point to make the city look slightly different in this project compared to my previous works. The projects that Nick and Blake Matthews have done left an impression on me. Blake depicts Chicago in a way that falls between raw and polished; there is an energy to his aesthetic and Nick’s skating that’s special. They do it the best if you ask me. Matt King contemporary videos fall into that category as well—pairing a rich, clean look with hectic skating, filming, and editing.

Kush Bulmer – Boardslide, Photo by Danny Klein
How do you make a project feel cohesive when the team is fluid?
Noticing people and the things that happen around them helped me find a common thread. Somewhere along the way I made it a point to maintain a bigger crew because everything became a shared experience; that helped me form some sort of guiding narrative.
Did filming different generations bring out different energies or processes?
Oh man…yeah. It was a challenge navigating energies but having everyone on session helped. More often than not, it made people more comfortable with one another; regardless of productivity. Interestingly enough, some people had no vision for what the video should be and others had a very concrete idea; like having something filmed a certain way. That tended to run counter to what I had envisioned. At the end of the day, I changed my techniques and made a video that represents the current scene, in a genuine way.
Genuinely, at what point does filming become difficult?
It’s hard when your personal life and career get in the way. During the course of filming, I went through an intense breakup, had some friends die, navigated career changes, and faced health issues that made filming exhausting. Filming was often therapeutic but I used it as a band-aid, ignoring painful things that I needed to address. At times, it felt like I was doing everyone, including myself, a disservice when I pushed myself to film instead of rest.
Towards the end of the video I got a little upset with my shortcomings as a filmer. There were times where I thought I was going to fail everyone. A few skaters came to me, voicing regret in not getting certain clips. I told them, “there will always be another video”, which is what I started telling myself to overcome stress. Stress is serious but it also shows that you care about your craft.
A project like this was just what I needed, but how and what I film in the future will change; I may want to make short films or work with brands. Skateboarding will always have a place in my life but I think it will look different as I move through my thirties’.
Since filming this project, what has been your most memorable moment?
It’s gotta be Larry and Max at Uprise asking me if I wanted to help make this video in the first place. I am fortunate to have been accepted by this community and backed by Uprise. Their belief that I could pull it off was huge and helped me move more intentionally.
It provided me the opportunity to befriend the skaters as well, which is equally as memorable. At the end of the day, I’m proud of the people in this video and what we made. Chicago is an amazing city for skateboarding and if the community keeps pulling together it can only strengthen the culture here and at large.

Martin Garcia – Boardslide Pop-out, Photo by Danny Klein
Photo by Hunter Brown