Wyatt Oleff

2 September 2019

Photographer Hannah Sider
Fashion Olivia Perdoch
Words Sophia Razvi
Groomer Walton Nunez

Though it was all work and none of the play that made Jack a dull boy, one conversation with 16-year-old actor Wyatt Oleff and you begin to wonder if ‘Jack’ was in the wrong profession.

Since setting his sights on acting at the age of five, It star Wyatt Oleff craves a busy schedule and is most satisfied when devoting his days to an industry that takes no prisoners. ‘Energy is always so high on-set that I forget that it is work’, he confesses; ‘sometimes that’s a bad thing.’ Currently based in Pittsburgh where he is juggling filming for an eight-part Netflix series (an adaptation of Charles Forsman’s graphic novel, I Am Not Okay With This), turning 16, and whistle-stop trips to New York, Wyatt believes he is finally right where he is supposed to be.

Photographer Hannah Sider paints a perfect portrait of a perfect muse: the poster boy for the rewards of mixing business with pleasure. With the anticipated release of It: Chapter 2, where Wyatt will reprise his role as Stanley Uris, the young actor already has two major franchises under his belt (at age 10 he played the young Peter Quill in Marvel’s Guardians of the Galaxy). Opportunities rarely fall into one’s lap sitting idle though, something Wyatt knows only too well. He is part of a new age of actors that really are growing up on the job, and when faced with a sea of ‘no’s’ decided to make his own project. Stylist Olivia Perdoch matches his high-energy work ethic with versatile looks and quirky details.

Wyatt will be gracing our screens in IT: Chapter 2, which hits cinemas worldwide this week.

You recently turned 16 - happy belated birthday! How did you celebrate? What are your goals for your 16th year?
I took a trip to Laurel Caverns with a couple of friends and it was amazing: it was everything that I could have hoped for. My goal is probably to get my license, which I think is everyone’s goal when they’re 16! I feel like that is essential when you reach this age.

How would you describe yourself and who are you?
I am a passionate worker who loves to work on - mostly film - projects. I am someone who tries to enjoy their time to the fullest. As I’m growing up, I’m realising how fast time passes and I try to really engage with the moment. That is something that has helped me in social situations: knowing what to say; being with friends and other people. That is mostly an internal thing that I’ve been developing.

What makes you happy?
Being with friends and family is one thing. Having a lot of free time is always nice. And sometimes after being with a lot of people for a while, it’s nice to just be alone for a bit: listen to music that I enjoy. A lot of things make me happy, but I’d say what makes me happiest is being with friends and just laughing at stupid stuff!

When did you realise you wanted to be an actor?
I guess when I was around 5, I was asking my mum to be on the TV shows that I saw as a kid; and I didn’t really know what that meant, but we lived in Chicago at the time so my mum was like, absolutely not! Then we moved out to LA when I was 7, and I asked again, ‘can I do it?’ and she said, "Fine…", so we tried it. I don’t really know what inspired me to act but I am just glad that my 5-year-old self was like, ‘this is it!’ because I love where I’m at right now and I feel like I could do this for the rest of my life.

It is one of the most iconic horror films of our time and one of Stephen King’s best-selling books. How did you prepare for the trauma when filming the scary scenes?
Well, I think the easiest way for the director and producers to do that was to just not really tell us what was going on in those scenes! They’d say, "So someone is going to be behind you but we’re not really going to tell you when… So good luck!". That factor of the unknown really helped because I was actually scared in those moments where I didn’t know what was going on. It's to the movie Alien, where they had the actors walk around the hallways and the alien would just appear. That kind of philosophy: telling someone you’re going to let go on three but let go on two. Stuff like that.

How did that experience compare with your expectations of what filming would be like?
Actually, I thought there would be more jump-scares, or just being scared in general! Half of our shoot was just us being kids and that was not what I expected - but I love it. I’m glad that that was the case because it really makes you care about the characters before you put them in danger, and that’s what you want: you don’t want to see your characters getting hurt. So when we had to film those scary moments, it wasn’t as familiar and that’s the best part. It felt like a normal summer but then some scary stuff happened, and that’s basically the movie as well.

Did you have a post-filming routine to help you ‘de-Pennywise’?
It was pretty lucky for us because we filmed the ending part at the end of our shoot, so we could share those moments. It really wasn’t hard to come down from that: though we were all at a pretty high emotional place, we all came down from that together. Us all having each other was such a huge benefit.

You are currently filming for new Netflix series I am Not Okay With This in which you play Stanley Barber. Tell me about your character. What similarities do you and Stanley share?
So Stanley is this ‘so uncool that he’s cool’ kind of guy. He does not care what anyone else thinks about him, so he’ll wear whatever he wants; he’ll say whatever he wants; he’ll do whatever he wants. I really enjoy playing that kind of character. Stanley is a bit of a joker: he likes to mess around and doesn’t really take anything seriously, so I can relate to that. But he is also very deeply caring for those that he likes to be around, and he cares about peoples’ health and wants the best for those people. That’s how I feel: when I want someone to feel better I try my best to do that.

What has been your most challenging role so far?
Right now, it would probably still be young Peter Quill in Guardians of the Galaxy I. That was just a lot. A lot of crying and basically nothing else. I think it was three days of filming and it was really tough on the psyche at 10-years-old. I’ve had a lot of emotional moments in my roles, but overall, it was those three days of constant crying.

How do you deal with rejection in the industry?
I like that question. Well, you just get it so much that you become de-sensitised to it! Personally, that’s been my experience. In the beginning, it’s really rough to start out and have all these people say, "No, you’re not right for this role". For the past 3 years, I have just had a lot of ‘no’.

Luckily, I’ve finally been able to get this new project and it’s because I have been waiting so long and constantly auditioning, and trying to put myself out there, that I am able to find a role that fits me, and that’s the most satisfying moment to have. I feel like I have earnt this role. For them to be like, "Yep, you’ve got this part". It’s such a wonderful feeling after all those ‘no's’. It’s like that saying: there’s always light at the end of the tunnel.

In the new project, I am Not Okay With This, you play again opposite your It co-star, Sophia Lillis. Is that a happy coincidence?
Well, I got the audition through and in the break down we saw that Sophia Lillis had been cast as Sydney, so we thought, ‘okay, now we have to try really, really hard for this one!'. So, I went in and had a really good time with the casting director, and she loved my performance, and I got the role basically! It was just a really great experience.

How much of an influence is social media on your day-to-day life?
I like that question too! I try not to let it affect me too much. I find myself addicted to my ‘explore’ page more than anything else and that’s the biggest problem. I try often to take breaks from it, but in terms of social media, I feel like I have finally reached a balance of what to post and what to keep private. I feel like I have established this line that I haven’t crossed yet… I think. It takes a while to get used to.

As a boy growing up in Gen Z, what does ‘masculinity’ mean to you?
Everyone can have their own image of masculinity. Obviously, for me growing up in Gen Z, it’s very different from what it used to be. I think the best change is that we're going away from the idea that ‘boys don’t cry’. I can be a very emotional person and I grew up with my mum who always told me that you shouldn’t be afraid to cry; you should let the emotions out. Masculinity isn’t about hiding your emotions anymore, it’s about being able to express them in a way that can be positive, and not being afraid to admit when you’re in a tough spot. I think that’s a great form of masculinity that allows boys and men to have this voice.

Which leads me onto my next questions, is Wyatt able to talk about emotions easily?
I feel like I am sort of good at it! I am a teenager right now, so I’m in that spot where there is a lot going on and it’s kind of hard to narrow down on one feeling. I feel like I can pretty do that pretty well for someone my age, but I have some years to go.

Do you have any outlets for self-expression besides acting?
A good one is drawing. If you’re ever really angry and you don’t know how to cope with it, just scribble on some paper: I find it to be a good stress reliever. Drawing, in general, is pretty soothing for me, or sometimes just writing stuff down in a journal.

You starred in and were an assistant director for short film Oh, Sorry. Can you tell us more about the project?
It was originally a feature film, but the writer, Maddy Coughlan, and my family and I just decided it would be better if we made a short. The project is about this one girl’s night and how it completely falls apart. It is kind of about being in that early 20s crisis - that obviously I don’t have yet - where a lot of people find that they are unsure of where they’re at. It explores that journey.

It’s our own little project. I have an interest in directing in the future and I thought this would be a good opportunity to be able to do that. Both my parents are executive producers on it. We thought, 'why are we waiting for a project to come to us? Let’s just make our own thing'. And luckily, we are in a position where we are able to do that. I’m really happy with it.

How was it to try your hand at directing?
It was very new. Especially as I was acting too, the first day was kind of weird for me: I had to make sure I was hanging out with the directors but also that I was ready for my acting parts. It was difficult to balance the two, but eventually, I was able to get the hang of ‘this is what it feels like to be directing and solving problems and making the scene’. It’s really interesting and I just love the process even more now because I have had that new perspective on it. I’m just excited to try and direct more and more things.

Let’s talk about your YouTube channel. It’s hilarious. What inspires your material?
Each video is very different. Some are parodies of things; others are just weird abominations of ideas.

The latest video, LOL, made me giggle.
That one is actually mostly improvised. My buddy Finn and his friend Josh were over at my house, and we were just hanging out and we thought, 'yeah, let’s make something', so we decided to improvise a scene. We only had one camera so we just had to follow the same beats and hope we matched them in editing. That film is edited by Finn but most of my videos are edited by me. I love making them.

How do you get yourself out of a dark place?
I feel like any time that I am in a dark place, it is usually because I am alone, and I am missing some sort of connection. So, for me personally, I try to connect with people that I know will help me feel better. I have this trust in people and I know the ones that will help me realise where I am at and stay grounded and be like, 'okay, I can get out of this'.

How do you practice self-care?
In the past, I used to have this self-esteem issue where I would make a lot of self-deprecating jokes and crack a little too many of them. That was mostly to try and put myself down. I wanted to stay humble, and I wanted to continue to stay humble… So, in my mind, I was thinking, ‘hey, if I put down everything I do as nothing then I won’t ever not be humble’. But my mum was talking to me about it and she was like, "That’s not how you should treat yourself. Of course, you should stay humble, but it should never be a case of 'oh, let’s make a joke about myself because I suck'". It was finding that balance - my self-deprecating humour still exists but it’s not in an unhealthy way like it used to be.

Making sure you don’t hurt your self-esteem or psyche too much is really important. Even if you think it’s helping you in one way, it could not be helping you in another. Trying to see multiple perspectives really helps.

Outside of acting, what are you passionate about?
I play a lot of video games, so I am pretty passionate about keeping up with the new stuff and also playing the retro stuff. I love drawing and writing down ideas. I have a lot of Rubik’s Cubes! The biggest one I can solve right now is a 5x5.

That’s a pretty niche interest! What’s your fastest time?
It’s about 50 seconds but I only know beginner techniques. For other people that’s fast, but for speed solving that’s pretty slow! Personally, I feel like I can improve but I also don’t want to learn the 200 plus algorithms to make it faster…

If you could send one message out into the world, what would it be?
Be kind to your planet. As most people know, we are in a crisis with global warming and I want to use my platform to tell everyone, ‘hey, our planet is on fire so we should probably do something about it!’. Any little contribution you can make is amazing, like use your own water bottle instead of plastic ones; it’s minor things but they really help in the long run.

I’ve spoken a lot about personal things here and having a healthy approach to self, but we must do what we can to help to make sure the world is healthy as well.


Above Left: Wyatt wears suit, shirt, boots, sunglasses by THOM BROWNE
Above Right: Wyatt wears shirt by WINNIE and trousers by WAN HUNG


Above Left: Wyatt wears shirt by WINNIE, trousers by WAN HUNG and boots by CALVIN LUO
Above Right: Same as before


Above Left: Wyatt wears shirt & trousers by ROCHAMBEAU and shoes by FILA
Above Right: Same as before


Above Left: Wyatt wears suit by DAILY PAPER and shirt by VICTOR LI
Above Right: Same as before

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