Ashby Gentry

With My Life With The Walter Boys, Ashby Gentry shows audiences his romantic and nerdy side and proves that he knows how to portray the guy from next door effortlessly – and how to get the girl.

Ashby Gentry is a name you should remember now. He’s an incredible conversationalist as well as a richly talented emerging actor. Now he’s taking over the screens on Netflix as Alex in My Life With The Walter Boys based on the popular novel of the same name by Ali Novak. The series follows fifteen-year-old Jackie Howard after losing her family in a tragic accident. Jackie leaves behind her life in New York and moves to Colorado to be with her guardian Katherine. Jackie is determined to stay focused on her dream of getting into Princeton all while wrapping her head around her feelings for two very different Walter brothers: the reliable and bookish Alex and the mysterious and troubled Cole.

The series seems to be all about a love triangle – at first glimpse – but for Ashby, it’s much more than that. It’s a portrayal of family, dealing with grief, finding hope again and navigating life when everything feels a little bit lost. He previously starred in Are You Afraid of The Dark – a teen horror series as Porter but Alex is Ashby’s first big role in a major setting. According to him, he’s here to stay and he’s not going anywhere. This is just the beginning.

1883 Magazine sits down for a chat with Ashby Gentry about his role in My Life With The Walter Boys, his life in New York, what he’s manifesting into the universe and more.

Firstly, congratulations on your role in My Life With The Walter Boys – your biggest role to date. How do you feel now a few days after its release?

It feels crazy. I sort of have no reference point for this. This is my first sizable project that’s coming out. I’ve only ever been very novel to all of this. I’ve only ever had one co-star, one guest star and now one series regular. So I have a very minimal amount of experience. And so this coming out, I was sort of like: Is this doing well, because it seems like it’s doing well, but I don’t know. I don’t know how to tell. I refresh my Instagram every 10 seconds and 100 likes are going through and I’m just like, I’ve never experienced anything remotely close to this. So excited. I feel very grateful. I feel extremely lucky. And I feel very proud of my cast and crew and the writers for doing such a thing that seems to me, for the most part, overwhelmingly positively received.

On top of that, I live with a friend from the show Corey Fogelmanis who plays Nathan, he’s my roommate. I was talking to him about it. And I was like, it’s weird, I feel kind of anxious all the time. Since this happened and I’m just wondering, who’s seen it? Who’s talking about it? Which of my friends are talking about it? What are they saying? I’ll be walking around and people will glimpse at me or doubletake and I’m like, do they know? You wonder if they know who you are because they easily could, especially given that we’re number one on Netflix right now. If you open up Netflix it’s right there. He labelled it very nicely, it’s almost like a paranoia. I’m paranoid for a very good reason. That’s been super bizarre to experience. With this, it’s just very much its first encounter for me, this is my first big role. When I encounter things that I’ve never encountered before and do something for the first time, I’m usually very gracious with myself. I allow that stimulus or project or phenomenon to just be an exploration. I think press and publicity and reception and notoriety are no different in that regard. That, for me, is just something new that I’m exploring. It’s fun, that is the number one word to use to describe the whole situation.

That’s the main part, that it’s fun! I can only imagine the anxiety and the excitement that you’re feeling with the whole release. I remember when we set up the interview, I looked up your Instagram and I think you had about 2000 followers and now you have 90,000 and it just keeps going.

I just hit 100,000. I can’t even conceptualize that. That’s so many people that it’s hard to even imagine. If you thought about all those people in a room, it would be overwhelming but you can’t think about it so it almost doesn’t feel real at the same time. I just don’t know what that means. It is nothing short of shocking, to be completely honest. I don’t think there’s anything I could have done to prepare for how it would feel.

[Editor’s note: Ashby is now at 332k]

Let’s talk about the show. You play Alex and there’s a bit of a love triangle happening between Nikki and your character’s brother Cole. How did it feel to act that out?

It’s interesting because when you think about the form the show takes, it is very much a love triangle story, right? That is the primary conflict this season, who knows what it will be in the future? I think that overall, holistically when we look at the show itself, the love triangle is not necessarily the primary conflict. The primary conflict is that Nikki lost her family and she is learning how to find her bearings again and find a new family in a new situation, despite that tragedy, I think there’s a colloquial misconception about the show that she’s choosing to be involved in this love triangle. And to me that’s false. It’s a false projection. Falling in love is not a choice that a person makes, it’s something that happens to you. Just like the tragedy that happened to her. So, the illusion that she’s choosing a love triangle when she should be grieving for her family is entirely that, it’s illusory.

What’s happening is she’s grieving and then all of a sudden these other emotions start filling in that void. I was very cognizant to not reduce the show to that of a love triangle show, but rather to view the love triangle as an addition to the underlying conflict, which is that this girl has to restructure her reality. I think two things can be true at once and it can be true that the foundation of the show is rather tragic. At the same time within moments of tragedy, there are also specificities of lightness and humour and cute adoration. With the love triangle, I always view it as an extension rather than a subtraction or a reduction. It is a part of the show, but it is not just the show, and I think that’s what makes us unique, at least in the reception I’ve received from audience members. That’s what people seem to like about the show. That there is more to it than that but I think it’s real. I think everything that happens to her is so real. I think it’s important to highlight that these things are happening to her, they’re not things she’s making happen.

I have not watched the whole show yet but it reminded me of The Summer I Turned Pretty when I first heard about it.

Yeah, we’re compared to them a lot. I think they’re similar elements, especially the weird coincidence that they’re both brothers. I think one of them gets punched at a bonfire too or something. I do think they’re very different shows, though. I think that the only similar element to their show is the love triangle which, again, is an interesting and super fun conflict to explore. I think that our show is also much much greater in scale. There are more characters, and more plots going on, which is not a diss to them at all. I think you can do both. I was initially nervous about that because I was worried people would think we were just copying them and so far, it seems like the inverse has happened where their fans are like: “Yay, we have another one.” I’m like: “Great. You can watch them both.” I don’t view us as competition to them. I view both shows as mutual support to each other, which is great. This is a little-known fact, I met Lola from The Summer I Turned Pretty at the SAG-AFTRA after-party this summer, and she’s really lovely. We took a selfie together.

When two worlds collide!

That would be crazy, wouldn’t it? A cross-over episode.

I think this is why the show took off so quickly because everyone loves teenage shows and love triangles nowadays no matter what age you are.

Yeah, because again, I think the reason for that is, these things happen to us, we don’t do them and they can happen to you at any age. I’m sure there are love triangles amongst the seniors at the old folks’ home, maybe they should make a show about that. They did one, The Golden Bachelor, I don’t know if you’ve heard of that.

I have! I was never involved in a love triangle and I don’t know if I want to be, to be honest.

I’m sure you don’t. It’s not a pleasant experience all the time. I’m telling you that. It was juicy though, it is juicy. [Laughs]

But they for sure are everywhere! 

And it’s so funny that people immediately put us in contrast to The Summer I Turned Pretty when there are millions of shows. Was there not a love triangle in Never Have I Ever? There are plenty of love triangles out there. The Vampire DiariesTwilight. I do believe that is the only similar element between our shows and their show. But it is impossible to talk about our show independently from theirs.

I think there will always be comparisons to other shows. It’s unavoidable. Let’s talk about your character Alex. I read that you love Star Wars and Lord of the Rings and Alex does too. What other similarities do you have to your character?

I think both of us are very intentional about things and almost bordering on the point of neuroticism, Alex can be very specific. There’s a scene where we all go bowling and he’s very particular about the lane and the time. We have to be there and I booked us a lane exactly like at 2:30 so that by the time we get there, we’ll have exactly 45 minutes in the arcade first, and he’s very specific with Jackie and with how he shows his care and I very much relate to that. I think a lot of what you’ve seen with him being in love with her is just the way that I am when I’m in love with someone. The biggest part of myself that I brought to the show was Alex in love. I think he doesn’t hold anything back and I don’t I do either. I think life is short and I’ve only ever regretted holding back when it comes to the love I have for another so I think that part of him is very much the same. And also we both have a good right hook. I don’t know if you made it that far yet but you’ll see. That right hook is mine in the show.

I’ll remember your words when I watch the scene. Why do you think viewers like Alex?

Alex isn’t attractive. I mean, this is up for debate. If you look online, there’s some debate about this. But Alex isn’t necessarily attractive in his content. He’s not attractive for what he is, he’s attractive for how he is. It’s his behavior and it’s his form that makes him a candidate for Jackie. I think viewers will like him because of the way he cares, because of the way he looks at her, because of the way he talks to her, because of the things he does and the choices he makes. I think that’s a reason to like Alex and I do think there’s some validity to his content. I’ve always said that Alex can’t win at Coles’ game. Alex has to play a different game to win. He can’t beat Cole at being Cole. He has to be something else and that’s the advice he has to use from his brother. He says you have to be Alex, you can’t be Cole. That’s very true. No one can be what Cole is. Alex has to do that. He has to play a different game to win. I think the more he leans into that, the more attractive he gets.

Not to be biased but I am team Alex. Can you tell me about your favourite moment of filming?

I think that, in general, it’s the way we bonded on set. I think people can see that we care about each other a lot. I think the moment that comes to mind for me is there was this one day when we were shooting a scene of episode one. This really quick scene where we all leave the house early in the morning to do chores, so we were in our chore clothes and the chore clothes are dirty. When we were filming this scene, there was a baseball bat in the corner of the room. I grabbed it and I said: “Hey guys, do you think if I leave the house with this baseball bat, anybody will know? Do you think they’ll say anything to me? Like why do you have that baseball bat?” Nobody said anything to me in the hopes that they were going to instigate bad behaviour or rather mischievous behaviour. So anyway, I did it. I left the house with a baseball bat.

Then, we moved on to tighter coverage, And I was like, “Oh, okay, so the baseball bat is in the show, it’s in the scene.” After that, the director Jerry Ciccoritti came up to me and he’s like: “So when you came out with a baseball bat, I thought, oh, now that’s interesting.” But that’s not my favourite moment. My favourite moment was after that, because I didn’t get my mischief fix we all went out. Back to behind the house, into the field. We took apples from the kitchen, and we threw the apples up and batted them with the baseball bat. We got three apples in before the wardrobe department started sprinting over to us saying: “Stop, you’re gonna get apples all over your clothes.” And I said, “These are my chore clothes.” And replied with, “Well, you still have continuity, Ashby.” So I think that was my favourite moment from the set because it highlights the spirit of what made the project so enjoyable, which was all the shenanigans we pulled while we were filming it.

That sounds so fun! Did you do anything special to prepare for your role?

It was a very primary experience for me. I did everything I possibly could, anything I could think of to do for Alex, I did. A lot of that just has to do with the foundation of any job as an actor within the text. So, rereading the script over and over and going over the lines over and over. I’m doing various things that I always do with any project, like analyzing the script and the scenes and the character’s intentions and stuff like that. Beyond that, I read The Lord of the Rings. I watched the Star Wars movies. I would ride horses. I had horseback riding lessons. Any week that I wasn’t shooting, I had a lesson on the off days so I learned a lot about horseback riding and caring for horses and I would make the food we would have in the show. I had a condo in Calgary and my condo had a nice kitchen, so I’d figure out what I was going to eat for the week. I thought, “Well, we’re having chili in episode one, so why don’t I make chilli and so I would do that.” I don’t know if it helped me play the character any more than it would have otherwise, but it was nice and it added some spice to my life because it gave me meal ideas for the week.

I would listen to a lot of music, there’s a lot of different parts to Alex. I would listen to a lot of Phoebe Bridgers but I listened to Sufjan Stevens, those are more of his romantic side. Then when it comes to the cowboy side, I listened to Bob Dylan, Townes Van Zandt and Blaze Foley and I think there’s this often hidden side of Alex that is very boyish and competitive in the way that Cole is. And for that I would listen to Drake. I would always say that Alex listens to Drake, but he doesn’t tell anybody that he listens to Drake. Other than that, a bunch of random ideas, anything I could think, I threw up a wall because I had no clue how to play this character. I just tried everything.

You put a lot of effort in. I haven’t heard of that kind of commitment before!

To me, this is a full-time job. Even on my off days, I would work all day. I would take rest when I needed to and I would go out and have fun with the cast because I think that feeds the work. The point of life is to enjoy it and so if I’m not enjoying it, then why would I do it? But yeah, I worked all the time. I was terrified. I didn’t know how to do this and I felt such an immense amount of responsibility that it was only right to work as much as possible, in my opinion.

How does this project feel different from another project that you worked on previously called Are You Afraid Of The Dark?

I’m so grateful for that project because it was such a primer for Walter Boys. Like I said, I’m very new. I’m very much a novice and Are You Afraid Of The Dark was so serendipitous because I got that job and was there for three weeks in the Dominican Republic. It was a dream but it was at the same time such a valuable experience insofar as learning how to be on set, learning how to work with a director, learning how to navigate being on location for the first time and so it very much felt like a warm-up in a lot of ways to Walter Boys, but that’s not to be reductive because I certainly didn’t treat it that way. I didn’t know I was doing well. I got Walter Boys while I was on Are You Afraid Of The Dark. But every project is different. I don’t ever worry about that because the difference will come to me. I always approach them with the same level of intention.

Even with Porter, my character from Are You Afraid Of The Dark, I still worked all the time. For me, this is a full-time job and so I always give it everything I have, knowing that it will never be enough and that’s okay because I think the beauty and the uniqueness of a character lies within the imperfections that an actor encounters when it comes to performing them. They’re very much similar in a way, it feels very much like you enter into a little bubble for some time. You’re in a little micro world and then you come out of it back into reality. I’ve been very fortunate to be in both projects. I’ve worked with great people. I did another project after Walter Boys called Mooch which was a SAG Interim Agreement project. It was just wonderful people I’ve been blessed to work with and to be surrounded by fabulous creatives, and there’s never been a problem. I’m holding my breath and crossing my fingers because I know that’s a rare experience for an actor to have but I’ve never had a problem with anyone on set. I’ve never encountered pretension or arrogance. Everyone’s just had their arms open and been excited to work. I hope I can continue with this fortune in the future because it makes me look back very fondly on all of these things.

I read that the showrunner Melanie Halsall immediately wanted you as Alex after you auditioned. What drew you to the role and how did it feel like auditioning for it?

I screen-tested for it right here in my room. I felt auditioning for this project was interesting. It was very matter-of-fact, it was never exciting. It was never like that. I came in, I did the scene and then I left. It never felt like anyone was tremendously excited about me. It simultaneously never felt like I was doing anything wrong. It just felt very much like I would come in, I would do the scene, Melanie would say, “Thank you very much Ashby,” and then I would leave. It’s so funny that this is so often the case. All of the projects I’ve booked are projects that I’ve auditioned for and then completely forgotten about within a week and then they come back to you and you’re like, “Oh yes, I remember doing that.”

I think what makes the show unique is that it’s a sincere show about family at its core. As I said, I do think there’s a love triangle and I think that’s fun and exciting. I hope that story continues to develop in the future because it is so interesting. But I think at the core of the show, it’s a show about family. It’s a show about a girl learning to replace her old family with a new family, not to necessarily negate that older family, but rather how do you find the line that underpins kind of what the show is about? It’s about a teapot that Jackie has and it’s like nothing is ever so broken that it can’t be fixed. I think that’s a euphemism for her. Her struggle with her family. Just because they’re gone, doesn’t mean she can’t have a family even if it’s not that family anymore.

When I read the pilot, immediately I thought of that. I had no clue it was a love triangle. I didn’t know that was what the show was about at all when I got the part. It was only after I got the part that I started reading reviews on Goodreads because I was in the Dominican Republic and couldn’t get the book. That’s when I was aware that there was even a love triangle in the first place. I was like, “Oh wow, this is different.” But I think that element — that feeling of familiarity that I had when reading the pilot — is what made me excited to work on the show because I felt like this is something people can connect to and at least to my naive gaze, it does look like that. It looks like people are connecting to that element of it so it makes me very happy to have worked on this.

You mentioned that you’re always working but what do you do when you’re not on set?

That’s a tough question. For me, because I’m a workaholic, I always view everything I do as work. When you’re an actor, even going to movies is work. It’s hard to differentiate because acting is the art form of essence. It’s the art of being a human. When we weren’t on set in Calgary, we would do so many activities. It’s kind of funny. We never intended this initially but we were kind of method in the way that we hung out. When we did the Thanksgiving episode, we had a Thanksgiving at my house and everybody brought a dish and then we said what we were thankful for and all that stuff. I remember, when we were doing episode nine, there was a county fair. That was concurrent with the Calgary Stampede which is the biggest rodeo in Calgary. A lot of the activities that we did, even as a group were very much related to the show, and we sometimes intended that and sometimes didn’t intend that but just bond. When you’re living in Canada for six months, it’s lonely if you don’t hang out with each other, and also we liked each other a lot. Everybody likes each other a lot on that show. We’d go to bars and bars, we’d go dancing and hiking and horseback riding, we went to Calgary Flames games and have Thanksgiving and go to the Calgary Stampede. We would do all kinds of stuff.

Tell me about a picture that you posted on your Instagram that reads Thesus as well as your name. Does it have a story?

It was my final project in drama school, it was during COVID. So typically the way my schoolwork is, when you graduate you do this thesis project. You perform 10 pieces of theatre of your choosing and so it’s two classical monologues, two contemporary monologues, a scene, a historical figure, a movement piece, a wild card, and then two more that I forgot. But because of COVID, we couldn’t do it live. I was fortunate because of my friend Alex Tucci who’s a writer and who went to school with me. I was able to assemble a crew. We made a film version of my thesis. My friend Jake Philip Morris is an artist and they assembled that graphic for me as the cover and they created a little poster for me. That’s the poster for my final project for drama school. That was a significant project because I didn’t have the best time in drama school. I was never really in anything. It’s kind of ironic, I was by experiential standards, the worst actor in drama school because I was the only one who was never cast in a play in the four years that I was there. That project for me was my only catharsis as an actor in drama school because it was the only chance I had to showcase any acting ability.

It’s kind of crazy, coming full circle to what you asked in the beginning. A lot of what’s crazy about Walter Boys is, even for the people who I went to school with, it’s like the first time a lot of them have ever seen me act because I just didn’t do any acting in school. It’s very much an introduction to the world, not only for me as a human but for me as an actor simultaneously as if those two things were separate. They’re very much interconnected but it’s all super surreal and it feels very mythological in a way.

That’s so cool! Do you have any dream actors that you would love to work with?

Oh my gosh, absolutely. I mean the list is so long. I think the names that come to mind right now are Mahershala Ali. I would love to act with Frances McDormand. I would love to work with Timothée Chalamet. I think any young actor should mention him, especially actors that look like me because he’s very much our blueprint in a way. I’m excited about the recent work I’ve seen from Barry Keoghan, Florence Pugh, and Lupita Nyong’o. I could go on and on, this list is huge. I think the number one person I would love to be in a project with is Willem Dafoe. I think, as an actor, he’s my role model. I love the way he approaches his projects. I love the types of projects that he chooses. I love the way he’s able to transform, but simultaneously he doesn’t always do a complete transformation because that’s not what the role calls for. I love his epistemology when it comes to acting, the way he thinks about it from a philosophical standpoint and how he applies that to his practice. So, he’s my number one. He’ll always be my number one, I think.

I’m sure it will happen. I’ll manifest it for you.

Are you manifesting it for me? Thank you.

My manifestations always have become true so far.

Well, when it does happen, I will come back and talk to you about it. I think we should set a date for that! [Laughs]

Let’s do it! What is one of the greatest pieces of advice that you live by?

Always assume the universe is on your side because you’ll never know. You’re assuming either way. When you assume that the universe is on your side, you look for opportunities. Whereas when you assume the universe is out to get you, you look for curses, and it’s more advantageous to look for opportunities. I think it’s in everybody’s best interest to assume that things are happening for them, as opposed to happening to them. Even if that’s not the case, you should still assume it is the case. I think it’s a smart technique.

That’s a good one. I’m a big believer in the universe too. As you said, everything happens for you, not to you. It helps to navigate life better if you think this way.

I don’t know how you can experience what I’m experiencing right now and not think that way. Truly.

What is something that you want to manifest for yourself?

I’d love to take a step forward. That’s not to say that I’m obsessed with this idea of transcendence or progression, because I don’t believe that, but rather, I think this is the thing I want to communicate most clearly in my communication when it comes to the show and in the future. I would like to manifest a segmentation of my status as an actor in this industry. It’s really important to communicate to people that I’m here to stay and that I’m not one of these transient one-hit wonder types who fly by the night young 20-year-olds who are obsessed with fame and attention. I truly view myself as an actor and I’ve been an actor for years. I was an actor before I booked this part, and I’ll remain one for the foreseeable future. I think it’s important to manifest the fact that I’m not going anywhere. I think I plan to stick around for as long as I can.

I look up to Bob Dylan, I view him in some ways as a father figure. Less so now but much more so when I moved to New York and when I was really getting started and I very much feel like a kindred spirit to him when he moved to New York and started playing at folk cafes in Greenwich Village in 1961. He said something one time that I so resonated with. There are so many things Bob Dylan says that people resonate with but one of them is that he said, “I feel like I sort of snuck in the back door while nobody was looking, and now I’m here, and nobody can kick me out, and there’s no way I’m leaving now. I’m here to stay and I’m sticking around since I got in at all.” I very much relate to that. I feel like I snuck through the backdoor and got in just in the nick of time and I have no intentions of leaving anytime soon.

What would be a perfect day in New York for you?

A perfect day in New York. I would probably go get a bagel for breakfast. I would go see a park because there are so many beautiful parks to see. Prospect Park, even the little parks, they’re tiny little room size apartment size parks. Those are beautiful. I would go to Soho and buy something. I just came from the Marni store in Soho. I’m flying to LA tomorrow to do press for Netflix, so I bought my outfit for that. I would go to Soho and buy something. I would go to an art museum or a gallery. I would walk the Highline north and go to Sarabeth’s for brunch or something or lunch and then see some friends because I think New York is unbearable alone. It’s crucial to have people around you. Maybe get some Italian for dinner, I would probably go to Via Carota, I’ve heard it’s good. I’ve never been there so I would try that. I would go see a movie at one of the best movie theatres that we have in the country like Metrograph or Roxy Film Forum. Then, after that, late at night right before bed, I would go with my roommate Liam — we always do this — we would probably see a late movie past midnight and I would go to the doughnut shop on either Astor Place or Sixth Avenue 14th Street, which is a 24-hour doughnut shop. They have these croissant doughnuts there that are so good. Liam and I would go there and we would eat doughnuts until our heart’s content. Then take the subway home go to bed and call it a night. That’s like my ideal day.

Sounds like the perfect day. I’ll remember all the places that you mentioned and I will write them on my New York list. 

You better give me a Germany list in return. [Laughs]

Absolutely! I know that you’re going to LA tomorrow which is exciting. What else is ahead for you in the future?

I have this movie coming out called Mooch that I was a part of, which is an indie film that we shot during the pandemic. I have no clue when it’s coming out but my director Jeff has been very supportive of the Walter Boys’ success. He’s very excited about the show and we talk now and then but I have yet to bother him and ask “When’s the movie coming out, Jeff?” I don’t know if they’re announcing it. They were supposed to announce it but I have no clue if that’s happening, but that’s coming out and then we’ll wait and see what happens with Walter Boys. If we do a second season of that, then I’ll do that. I am very much eager to work on a new project. I don’t often set goals, especially when it comes to getting projects because that’s so out of my control as an actor, but I really would love to do some theatre. I would love to be in a play in the future so that’s something I’m craving right now. It’s the chance to step on stage because it’s been a long time since I’ve done that. I feel like I’m a horse standing at the gates and I’m just ready for the gun to go off so that I can sprint full speed ahead.

So there’ll be lots of exciting things happening for you.

Well, fingers crossed. I think it’s important to find excitement within the offseason too, and I try to keep life as exciting as possible even without all that, so when it does happen, it’s insane. That is what I’m experiencing currently.

My Life With The Walter Boys is streaming now on Netflix.

Interview Maja Bebber
Photography Chelsea Gehr
Styling Sara Attias
Editor Kelsey Barnes

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