Damon J. Gillespie

The soft tones of guitar paint the stoney walls, creating a sanctum against the cold streets of Manhattan. The atmosphere at photographer Jill Greenberg’s studio feels like a warm chai-latte against frozen fingers, inviting and untroubled. Under these strict conditions of comfort we meet Damon J. Gillespie, 25-year-old actor, acrobat, musician and dancer who effuses stardom in his essence. It is hard not to be beguiled by Damon’s Southern drawl and intriguing ascent within the world of performing arts. The tangential element of the conversation is certainly not tedious as Damon unflinchingly bounces between defeating bullies, playing multiple instruments, knitting and being whisked away to the world of ballet.

As Damon whirls in his chair, he shares the story behind his performance as headstrong but heartfelt Caleb in the new Netflix Drama Tiny Pretty Things, an adaptation of Sona Charaipotra and Dhonielle Clayton’s work of fiction. Never stagnant, his ever-expanding artistic portfolio earned Damon a place on Broadway, aged 20, and later on Inside Amy Schumer and NBC’s RISE. Growing up as a professional Hip-Hop dancer, Damon reflects the narrative of a character who is not easily defeated, whilst embarking on his journey of self-assessment during lockdown.

In the studio, toasty lights glimmer against the autumnal colours that stylist Jamie Ortega lays on Damon. There is an uncanny air of authenticity as Damon travels between outfit changes in coffee-break-perfect knits, soft tailoring and earthy hues. It is a controlled dance move here, a buoyant laughter there, an airy chord on piano leading the devil-may-care kick-flip. "My circus teacher always said keep filling your bag of tricks," Damon laughs. "People don't remember what you do for them, they remember how you made them feel." Nothing is too subdued as we peel away the beautiful gift and curse of being an artist.

Let’s start with the essential. Who is Damon?
I am a Southern boy from Tennessee. Growing up, I did everything: mixed martial arts, piano, guitar, bass, drums, football, basketball and baseball. I always find something new that I can learn as much as possible, the best I can. That's kind of who I am.

You never seem to be still.
No, never. I can't sit still. I don't like sitting still unless I am sleeping.

During lockdown we were put on pause, it must have been hard for you.
That's actually why I started to dive deeply into my music. I was learning more about it because I never got to study it, so I taught myself. I watched Youtube videos over and over, through trial and error - while annoying the absolute hell out of my roommates! During lockdown I also learned to trust my gut. I learned how to self-assess and identify what I'm feeling - when you're alone with your thoughts for hours on end, you start to discover a lot more. You had to just sit with whatever is going on in the world or going on in your life.

Music is your getaway. I heard that you're working on an album at the moment. What can we expect from that?
I've been working on this album for a long time. I'm finally in a place in my life where I feel comfortable doing it. I don't know when it's going to be released because I'm just now getting to the point where I can write stuff that I'm proud of. But it's going to be a conglomerate of different styles: rap, rock, r&b.

What was holding you back before?
The knowledge. A lot of the stuff I was writing before was repetitive and simple. Initially I wanted to learn how something is written, why it's written this way, where it came from and how can I simplify a sound to the ear.

That kind of comes across in my music through the addition of blues and jazz. When I started adding different elements - drumming is probably my favourite, I think I'm a percussionist first - I added more complicated rhythms and I started to gain confidence.

You grew up as a professional dancer, starting at the age of three. In what ways has this shaped you as a person?
It has taught me a lot about myself and how flawed I am. It has taught me a lot of self-discipline within the last 10 years. Growing up as a dancer, I didn't realise how fragile the body can be. So I've learned more and more about the body and how to take care of it.

How is it shaping you as an artist?
I used to act through my body because that’s how I tell stories. So depending on whether I'm in theatre, television or film, I have to be able to maintain that discipline to either be big or very small, but still be able to tell the story and connect with other people.

What was your experience as a male growing up in world that has traditionally been regarded as feminine, like ballet?
It was rough until I went to a performing arts school. And even then, it was rough. I got called names and was made fun of. There were times when I was even getting paid to do something and I was still being made fun of for dancing, singing or performing because it was considered corny. But then I started to realise what a gift I was given. I was a good-looking guy surrounded by a bunch of gorgeous women. It kind of felt like I had won the fight.

I started to understand how much strength I had. As I got older, I started to notice that my legs got much bigger than everyone else's. It kind of baffled me like, 'wait a second, why are my pants not fitting the way yours are?', and when I realised that dancing was giving me so much strength I stopped caring about others opinions. I'm so glad that I did and I finally understood the gift.

How do you overcome life’s moments of self-doubt?
It starts with the constant rejection. You see people who are completely different to you get the role that you went up for and so many things go through your head. There are a few methods that I started to adapt. One of them is to understand that your job as an actor is unpaid. That's how you have to look at it. Your job is getting an audition, an opportunity to play that character in your performance. If you book the job, that's the side hustle. That's what's going to pay your bills but your job as an actor is to act, tell a story and then let it go. Once you accept that acting doesn't pay, the side hustle pays, there's a lot less at stake. And that is what has helped me with the rejection part. I don't think I will ever accept when someone says that I couldn't do something because they were looking for a certain stereotype. I want to show them what I am capable of and prove them wrong. And it's not an arrogant thing - at least give me a chance. I always seek for a chance, not acceptance.

What drew you into acting initially?
When I went to performing arts school, I was a dance major. And I started watching a guy - who is actually one of my best friends now - perform as an actor, a dancer, and a singer. I started to hear different musicals, being in different plays and performing more. I started to fall in love with the idea of performing. And my mum always knew that I wanted to do that. That's why she put me in a performing arts school. Because of that, I started studying a lot more, reading more and I just fell in love with it. And if I don't have acting, at least I can still be an artist with something else, like my music.

What does it mean to you to be an artist?
You know, I think about this a lot. What is the purpose of an artist? I think it's our job to inspire people. And that's one of the biggest things that I've tried to lean into is that I don't want to lead people, I don't want to tell people what to do. I want them to be inspired enough that they can make their decision, they can get the confidence and then go after what they want and what they love.

How would you advise somebody that wants to do acting in their career? How should they approach it?
Read everything. Understand the history of everything. Start with Golden Age plays, then move on and find Pulitzer Prize-winning plays, then venture off and read some Shakespeare. You'll start to understand where a lot of the stories are coming from, and why they were written the way they were.

People don't remember what you do for them, they remember how you made them feel. So if you do something and impress them, they want to know more about what you can do. And they're gonna bring you back again. It's a chain reaction which starts with how you impress them with one thing and they want to bring you back in again. And then you keep impressing them and they're going to hire you. It may take a long time. But persistence is key.

Speaking of impressive, I was blown away by the dance scenes in the new show, Tiny Pretty Things.
And I truly can't say enough about our cast because they're just incredible. When I first got to Toronto where we filmed, I was blown away, too. I was asking our dance coordinator if I am in the right room. Are you sure you want me here? Because ballet is not my forte, I can do it but I need a lot of work. So I kept asking if they were sure? And they said yes. I was trying to make it my forte and keep up with everyone else because I was blown away by how amazing the cast was.

Tell me about your character Caleb, what is your favourite thing about him?
I think my favourite thing about Caleb is his loyalty. It's almost impossible to break his loyalty. In the show, he is always struggling with what's right and what's wrong. He's a very self-aware person. And that's what I can connect with - his loyalty and his self-awareness.

The show takes place in the highly competitive field of dancing. Having your own background in the industry, how were you able to relate to him?
There's something later in the season where Caleb has a moment with one of the faculty. He says a lot of stuff that I wish I could have said when I was in high school. But because of that competitive nature and rule to respect your faculty, you don't disrespect the room. You have to stay silent.

What do you want the audience to take from the story?
I want them to see that it's okay to challenge tradition and old processes. Ballet, dance, or being an artist in general is very competitive. We are the product as artists, so we have to give ourselves as a product. We're being judged on what we live with every day, so I want people to take away that there's nothing wrong with being "imperfect". Even as an artist, nothing is picture perfect.

Do you think that attitudes towards arts are changing amongst the next generation of boys?
Yes, I do. I think the outlook of what it means to be an artist is changing. Because of lockdown, we truly saw where artists stand. Without being shady or being a jerk, the performing community 100% saw how everything was handled.

I think shows like Tiny Pretty Things can help, especially with characters like Caleb. He is Southern bred from a military family and somehow, a curly-headed biracial dude is doing ballet! The stigma that people of colour can't do ballet, that boys can't be in that world unless they're gay, or extremely feminine, is an obsolete narrative.

What advice would you give to a boy who would like to explore the world of ballet, but doesn't have the confidence to do it?
I would say: 'Think about how it makes you feel.' And then look at everyone else. Do they actually seem happy? If not, then don't worry about it because they're projecting their insecurities and their unhappiness onto you. Go for it. The best way to defeat a bully is to show them exactly how flawed their logic is and how dumb they sound when they say certain things.

That's pretty good advice to any life situation. But what if the pressure gets really high, how do you decompress?
Especially during lockdown when I was extremely stressed, I would go to music. When my fingers would start to get numb or I couldn't lift them off the piano, I would turn to Avatar: The Last Airbender and that put me in a state of peace. It brought me into meditation.

You are quite the multitalent, but do you have a favourite creative outlet to relax?
I actually have two. I love getting on my computer and doing audio production. I've spent 12 hours mixing, mastering and recording a song in one day. I even ordered food in. It occupied my brain that much. By the time I sat up, it was 2:30 in the morning and I had to go to bed.

The other thing is knitting. I started six years ago because I didn't have money for Christmas gifts. So I bought a needle and some yarn and made my first scarf. I've been knitting ever since. That's what I do if nothing else is working. I'll throw on some television and or a podcast and just go to town.

How do you tune into a character?
When I get a script or a character, I tend to write everything down about him and create certain aspects: who does he love? What's his favourite food? Then I go through the script and identify what is the objective in every scene. Once I identify that, I take the characteristics and go, ‘how would Caleb go for this objective? Would he be aggressive or would he be sneaky? Would he be manipulative? Would he be damaging?’ And so I kind of figure that out and go from there.

I was also thinking about why it is important to be yourself, especially in an industry that is super competitive. How do you stay true to yourself?
I'm going to quote Snoop Dogg. Uncle Snoop said "Who can be you better than you.". That's why it's important to bring "you" to everything. The audience doesn't want to see the same thing. Eventually, they're going to want to see you. TV, movies and theatre all move us in some way. And sometimes, we can't just keep getting moved in that way: you need variety. That's why they want to see you in your most authentic self

It is easy to compare yourself to the people you're working with or competing against. How do you stay grounded?
That moment came when I finally just said I don't care anymore. I'm this nerd who loves video games, anime and will also rock out to Slipknot and Kendrick Lamar. You know the moment you just go: 'I like this and I'm okay with that' is the moment when you start to be authentically yourself. And it also brings yourself to a character or an audition.

Yeah, I actually saw this quote a few weeks ago that read ‘you can't change people's minds, but you can change how you react to them.’
And that's why I came up with this motto when I was in Toronto last year: to be assertively kind. You can tell people what you feel. And you can tell them what you want and what you don't. You can do it in a nice way that still gets the message across.

There's one more thing. I started to not worry about things by going through the worst possible scenario. When you think about it, you realise the worst thing that can happen isn't that bad. And that brings a lot of comfort.

Exactly! You just do it again, until it goes right. Like dancing: you do the jump until you land.
Yep. You go and you do the turn until you get that third, fourth or that fifth one and you've landed it perfectly.