Ashby Gentry

Since stepping into the role of Alex on My Life with the Walter Boys, the younger and somewhat meeker of the two brothers who form a love triangle with the show’s heroine, Ashby has transformed his approach to the character with each passing season, relying more and more on his intuition than the strategic disciplines that used to define his work. With more experience under his belt, he recognises acting as both a craft and an exploration, allowing himself to trust his understanding of who the character is in a given scene over rigid preparation. His approach is deliberate but fluid, reflecting a deep understanding of his job on a set and his desire to continually evolve—not just as an actor, but as an overall filmmaker as well.

For Ashby, the projects he takes on and the roles he plays within them always depend on the story being told. He finds himself drawn to those simply about life, viewing each day as an opportunity to observe, adapt, and draw on material for what he calls the “best stories.” Stories he will likely have plenty of, thanks to his penchant for spontaneity, of which he is aware and proud. His overall love of life and experiences comes across in the way he shares easily, the stories he chooses to tell and the overall flow of our conversation as we move along threads that focus on his past, the present, and what he hopes to achieve in the future.

Let’s jump right in. Right now, while you’re in between projects, what does your typical day look like?
It depends. My day-to-day in New York, or when I don't have anything to do, is pretty structured. The problem happens when you're in between projects; you always have something to do. Because your schedule is open, it fills up quickly. You have no excuse for not being somewhere. Does that make sense?

It does. I would say that’s mostly a good thing. But, I bet there are pros and cons.
There can be.

So you’re based in New York. I love New York. It’s such a big place. What are your three must-dos for anyone who has a day in the city?
You have to eat some New York pizza. You have to walk somewhere. I would recommend either the West Village, Times Square or the High Line. And you need to take a taxi.

A taxi and not the subway?
Actually, I will say the subway. I feel like you're going to have to take the subway. But hailing a taxi is a canon event.

Do you think you're good at it now that you've lived in New York a while?
I'm an expert. I think a mark of being a seasoned New Yorker is knowing the cross streets of a place and knowing what trains to take to get there. Or, when something goes awry on your journey, not having to put it in Maps and knowing how to correct the situation.

That's impressive. I don't think I've ever been able to do that anywhere. I'm very reliant on my Map app.
The trains are just like streets. I always explain it to people like that. The 405 is like the NQRW or the ACE, you know? The left side is the HOV lane, and the right side is the normal lane.

And you just learn it eventually?
Yeah, it's very similar.

What have you found to be the biggest difference between New York, Los Angeles, and Calgary, since I know you spend a lot of time there?
I think Calgary is a good middle ground between New York and LA. It's a lot smaller. Calgary is walkable, but you can also drive around there. LA is not walkable. New York is walkable. I like to visit LA, but I don't really have any desire to live there. New York is like a Red Bull. LA is like a matcha, you know?

[Laughs] That's actually a really good analogy.
New York is high energy. LA has a relaxed energy, I think.

For those who don't know, Calgary is where My Life with the Walter Boys is filmed. You’ve completed production on season three. What has changed most on set since the first season?
We all have so much more experience now, and it feels so much more familiar. For instance, this past year, I started learning lenses—the lens sizes they used during production. It got to a point where, during the last week of shooting, I could confirm which lens they were using for each shot with our camera operator, Ryan, and I knew what that meant for the frame based on where I was in relation to the camera. I don't think that's a skill that an actor needs. But for me, it was a sign of how much I've learned since season one. I think those little things—the little ins and outs of a film set—are what we've all picked up on a lot more.

That’s really cool.
Funny story about Ryan, our camera operator: Before shooting season three, he was in Europe shooting The Odyssey with Christopher Nolan, because Ryan is Chris's favourite camera operator. Ryan had to ask Christopher Nolan, "Hey, can I please leave production early because I have to go start this show?" And Chris was like, "Well, what's the show?" So, Ryan told him, and everyone on The Odyssey was making fun of him for having to leave for Walter Boys. [laughs]

Wow. What a testament to the team that puts your show together, in more ways than one.
Right? And you know what? I would have also made fun of him for leaving The Odyssey. But we're grateful to have him because he's the best.

As you learn from being on set, do you have any interest in stepping into any other positions?
Yeah, absolutely. I think acting scratches an itch that directing can't, and vice versa. They satisfy different creative parts of yourself. I’ve directed one thing before, and I’ve started to notice the more holistic part of myself that directing indulges is feeling neglected.

This is the cheesy answer that I've said to a lot of colleagues and contemporaries, but I mean it: I truly think of myself as a filmmaker. My goal when I'm working on something is to help the film get made. So that has, up to now, manifested in the form of acting. But my focus as an actor is not on me. It's about making the movie. I have a couple of projects in mind that I want to make, and I don't know what role I'll have in making them. They will need to be written, directed and acted in, and my role will depend on what season of life I'm in when I get around to actually making them.

I think the more that you know about what you’re doing, no matter what that thing is, the better off you will be.
For me, it’s all about the story. The source material is the most important thing. From there, the way I want to interact with the source material is an intuitive and circumstantial decision.

Speaking of source material, My Life with the Walter Boys is an adaptation. Do you find having full fleshed-out source material helpful as an actor, or does it hinder your typical process for figuring out a character?
I feel like building a character is like creating a soup. You can put too much of anything in a soup, and it turns bad, but also if you don’t have enough, it could be made better. It just depends. Anything helpful as an actor can be a hindrance in a toxic dose.

In this instance, I read the book. Actually, when I was preparing for season two, someone photographed me reading the book on the subway and put it on DeuxMoi. [laughs] I don’t read it anymore because I feel like we’re so far away from the book that it’s outlived its usefulness. But for the first few years, I was very diligent about trying to incorporate parts of the book into the character.

I’ve heard other actors say that playing the same character season after season can be a marker of how they’ve grown either personally or professionally over the years. You change as your character does in ways that are either similar or different, and it's easy to compare and contrast. How do you think you’ve grown the most since you landed the role?
As an actor, how I work has changed, and my paradigms about acting have shifted slightly. This project has very much felt like grad school. I went to undergrad for acting. I have a BFA. Then, I went straight into this. So, it felt like a test of what I learned. I’ve learned what works, what doesn’t work, and how I like to work. I’m really eager to see how season three goes. I haven’t seen it yet. I’ve only seen little bits and pieces. I’m curious because I changed my approach pretty significantly in season three. I want to see if it helps.

What did you learn about how you like to work?
I’ve learned that, like most things in life, acting is an ultimately intuitive process. For instance, you’re a journalist, and you do interviews. You have your list of questions, but ultimately, the interview is conducted intuitively. If you feel like you want to ask a different question, you ask it. If you feel like maybe you shouldn’t ask something, you don’t. Just because you wrote a list doesn’t mean you stick to it. And so it is with acting.

What I really focused on in season three was making space for that intuition. My process, to put it simply, was to prepare to learn as much as I could, to make discoveries about myself, and then show up and just be that person on the day. I would do nothing before shooting. If I felt stiff, maybe I’d stretch out or warm up, but I wouldn’t do any preparation. I wouldn’t think too much. I would just go by feel and really let my intuition take the driver’s seat. If I got a note, then I’d start thinking more, but otherwise I deliberately left it up to my instinct. Whereas before, I might have set intentions or had ideas about the tools I could use in certain situations or scenes. This year, it was about trusting that I know who Alex is because I’ve played him for two years, and then allowing myself to play and pretend to be him.

How do you think the character has changed the most since season one?
In my opinion, the whole show for him is a maturation. But I don’t think we’ve witnessed that growth yet. Currently, he’s lost in the woods. I think he’s finding his way out. It’s kind of a sad arc, actually. [laughs] I hope he gets some redemption, but I don’t think we’ve seen the positive side of it yet for him.

It’s a slow burn.
Yeah. I think he’s finding out who he is. He’s growing. It’s interesting. He always feels like a new character every time I go back to it.

That keeps it fresh for you. Speaking of change, you’ve spoken before about how much your life has changed since the show took off. I think change is a good thing, but is there anything you miss from before?
Sometimes I miss feeling “fresh,” which feels kind of ludicrous because I’m still so young and green and have basically only done this show. When you’re anonymous, you’re almost like a jack-in-the-box. No one knows what you can do until you show them. I miss that sense of mystery. People didn’t have preconceived notions about what I could or couldn’t do. Now that this is out, now that I’ve revealed myself a little bit, so to speak, people immediately make judgments and observations and classifications about me, whether they realise it or not.

But I deliberately keep parts of myself private to preserve that feeling of potential. And honestly, I don’t think anyone really knows who I am. There’s only a very small part of my identity that’s been revealed through the show. But now, people think they know me. I miss not having that a little bit.

What are three words you’d use to describe yourself?
Counterintuitive. Pensive. Jovial.

Are those the same words you think others would use if you weren’t around?
“Pensive” is from someone specific. He calls me pensive all the time. If I had to guess how people would describe me, I would say I’m smart, funny, and surprising. But I’ve always said I’m unpredictable, but also unsurprising. Even to myself. I’ll do something I wouldn’t necessarily expect myself to, but afterwards it’s like, “Of course I did that.” Other people react the same way: “Of course he did that,” even if no one predicted it or could have predicted it.

So there’s a kind of consistency in the unpredictability.
Yeah, exactly. I’m consistent, but always moving forward. I’m kind of like a shark. I’m consistent but novel at the same time, and I think that’s the contradiction people struggle with.

Is there a specific moment you’re willing to share where you surprised yourself?
I’m supposed to be going to Coachella in a few weeks. I told Nikki [Rodriguez] and Noah [LaLonde] about it, and they were kind of like, “What? Why are you going to Coachella?” Because it's not at all my scene. And then I explained, “Well, I have some friends who were going, and they made the process really easy for me. My agent is getting me tickets, so it was laid out like eggs on a plate, and so I decided to do it.” That's how I am. I don't turn my nose up at that stuff. I'll show up to whatever if the door is open. That’s how I operate. Throughout my life, people have always been like, “Of course, he did that. Of course, that happened to Ashby. If it happened to anybody, it would be Ashby.”

The biggest example is the show and how it has played out. I was in drama school for four years. I was functionally miserable and arguably the worst actor in drama school. I was never in a single play. Then, basically immediately after, I’m on a show that millions of people watch. It’s contradictory. People will look at that and say, “Of course he did that.”

On this same kind of thread of telling stories, and to tie in what we were talking about earlier, of there being a couple of projects you would like to bring to fruition, what makes a good story to you?
I think the most interesting story is the one you live every single day. All good stories borrow from that. I was talking with a friend about this recently. I have some friends who are trying to be filmmakers. We've met a couple of times about it. We were talking about adaptations. And I said, “You guys should start reading because a lot of great movies are just adaptations of books.” For instance, when I read Cormac McCarthy, it feels like it's all right there in the novel.

I've always admired people who are capable of original thought in that way. Like, how did Cormac McCarthy think of this stuff? And then I realised they just steal from their life. You steal and hyperbolise. I think the best stories come from a person's life because having an interesting life is a choice. I believe you can’t control whether your life is happy or sad, but you can make it interesting. And that’s where the best stories come from.