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How A Painter's Insatiable Curiosity Led To A Bright Future

When Riley Holloway painted his first portrait, he was nervous and a bit unsure of what lied ahead. Now Holloway is getting shout-outs from celebrities and showing at Miami Art Week.

by Hady Mawajdeh 17 Nov 2016 6:45 PM
Riley Holloway

The 27-year-old painter is a self-taught multimedia artist who primarily works with oil paints, pens and chalk. His work mostly consists of large-scale portraits painted on 6-foot-tall, self-built panels. The people in Holloway’s paintings are the people he knows. In fact, his most recent solo exhibition at Fort Works Art was titled “The People I've Come to Know” and featured his mother, Dallas rapper Topic, Holloway’s wife and other people from his life. Holloway has spent time in Italy studying portrait painting at the Florence Academy of Art. He was Artist in Residence at The Fairmont Dallas. And he's showing work at SCOPE during Miami Art Week this November.

Jump to the Q and A


Welcome to the Art&Seek Artist Spotlight. Every Thursday, here and on KERA FM, we explore the personal journey of a different North Texas creative. As it grows, this site,, paints a collective portrait of our artistic community. Check out all the artists we’ve profiled.

Riley Holloway is quiet, almost shy. He’s always been that way.

“I was a cautious kid,” says Holloway. “I would take drawing and painting inside the house versus going out.”

When most kids were building forts or looking for trouble, Holloway says he avoided it. “My cousins were a little bit looser than I was. Like they’d be like, ‘Let’s go over there!’ and I’d be like, ‘But they can’t see us over there.’ I was that kid.”

His love for art was passed down by his mother who he says was a natural artists.

"My Mother" - Riley Holloway

“My Mother” – Riley Holloway

“She painted a lot. She was also a sculptor and sewer,” says Holloway. “She actually made clothing from scratch. But her real job was with JC Penny. She was a page layout artist back in the day.”

Holloway says that his mother was always encouraging his artistic abilities. She even played with him, so that he knew that art was important.

“We were doing watercolor painting when I was really little. And instead of buying me coloring books, we would make drawings together and I would color those in,” says Holloway.

At 27, Holloway is still thoughtful and vigilant. That approach put him on a path many artists would envy.

“As far as Riley goes, I think that the opportunity that he has is a potential game changer,” says Lauren Childs.

Childs has known Holloway for three years and recently her gallery Fort Works Art began representing him.

A shot of Holloway's solo exhibiton, ""The People I've Come To Know" at Fort Works Art in April, 2016.

A shot of Holloway’s solo exhibiton, “”The People I’ve Come To Know” at Fort Works Art in April, 2016.

At the end of the month, they’re headed to Florida for Miami Art Week where Holloway’s work will be featured at SCOPE – an art fair visited by thousands, including collectors, dealers and celebrities.

She says his reserved approach sort of helps him out.

“I don’t think he realizes how many eyes are going to be on him,” says Childs. I think that’s good. I think if he realized what was about to happen that he might be a little bit more nervous, so it’s probably a good thing.”

Childs believes that Miami Art Week has the potential to really expand Holloway’s reach as an artist.

“Potentially this could shift and impact his entire career and put him on a whole new level,” says Childs.

That’s something that Holloway seems happy about, but Childs says his cool temperament doesn’t allow for him to overly enthusiastic.

“Riley is very non-effusive with people, so the excitement doesn’t come across. Like when Swizz Beatz posted on Instagram about his artwork we talked and he seemed extremely proud, but after the excitement died down, he went back to being himself. I think that’s important for him,” says Childs.

Despite Holloway’s protective nature, he’s always been open to learning – it’s a passion.

“It’s always been like this big curiosity for me,” says Holloway. “I’ve always collected books on learning art and things like that.”

Holloway says he has hundreds of books about art and about painting portraits. The fascination started at a young age, but desire to really learn how to do it really took hold in 2011, while he was studying motion graphics at Art Institute of Dallas.

At the time, he didn’t care much for the design work he was doing in school, so he looked for people in North Texas who could help him obtain the knowledge needed to paint with oil.

“I remember a lot of the professors at Art Institute doubting me,” says Holloway.

Eventually he began to teach himself using YouTube videos and DVDs. He says there’s actually a painting he completed that he credits for giving him the power to drop out of the Art Institute. He still keeps it in his studio.

Holloway’s studio is located in Dallas’ design district. The walls of the studio are lined with his paintings. The paintings are six foot tall portraits of people from his life. Mostly black and brown people. He walks past all of them to a stack of paintings in the corner and pulls out a small green canvas.

“This is it right here,” he says. The portrait is unlike almost every other portrait that Holloway’s painted since he’s become a professional. He says that when he first began painting it that he was nervous and a bit unsure of what lied ahead.

“It was like a first date or something. It was like, ‘I don’t know what this is gonna be like but we’re both about to find out what I can do,” says Holloway.

After that, he wanted to know more about painting darker flesh tones, about properly lighting his subjects and he wanted to take his study of the figure to the next level

“For me it started inside out,” says Holloway. “You know learning to draw anatomy was a big thing. I was so curious with drawing anatomy and the language of that – of how to draw a figure.”

He filled sketchbooks with arms, torsos and drawings of friends. Then came an opportunity to study in Italy. At Florence Academy of Art, he studied anatomy in depth.

“Some of the things I was doing in the sketch book that I was kind of felt like I was making up, I was seeing there!” says Holloway. “It got to the point where they were telling me like, ‘If you come to the school and you graduate you could be the professor of anatomy here.’”

That experience gave him the confidence to apply for a residency in Dallas.

The video above is from 2013 when Holloway was Artist in Residence at Dallas’ Fairmount Hotel. 

“So that’s when I really felt like okay well I’m going to try this professional career at art. That’s when I really gave it a go,” says Holloway.

In the almost four years since, he continues to focus on portraits, but his style has matured.  He’s moved away from mixed media and incorporating poetry into his work.

An example of the mixed media artwork that Holloway was doing in the beginning of his career.

An example of the mixed media artwork that Holloway was doing in the beginning of his career.

“I had a lot of emotions and didn’t know exactly what to do with them and so I just threw them all on the canvas,” says Holloway of his earlier work. “At that time I had no balance. Now it’s more thought out and I think that’s just part of growing.”

Today, Holloway works to paint his subjects – friends and family – more truthfully. It’s an approach similar to that of his mentor, the painter Sedrick Huckaby.

"Sedrick Huckaby" - Riley Holloway.

“Sedrick Huckaby” – Riley Holloway.

Holloway says Huckaby has plenty of advice to lend him, and it’s not always about putting paint to canvas.

“He sees me as a young artist trying to figure out the career side, so he kind of coaches me on that aspect. He would like me to go back to school for that,” says Holloway.

Holloway might do that one day.  Right now, he’s concerned about providing for his wife Kelsey and their two children. He does a lot of freelance design work, but selling his work gives him a new appreciation for painting.

“The fact that it’s helping me feed my kids kind of strengthen my love for it in a way. I loved it before. Unconditionally. But when it starts to take care of people you love, I think the work reflects that,” says Holloway.

Holloway hopes people will see that and feel that when they encounter his work.

How does being in North Texas affect the production of your art?

I’ve got to be honest and say I don’t know. I don’t. I would need more exposure to the outside. I haven’t done much outside of North Texas, so maybe that’s how it’s impacted my art? You know, cause I’ve only worked here so far. The first time I’ll be going out of the state [with my art], like the whole state, will be for SCOPE and that’s this month. Then I’ll know.

For me North Texas has been a platform though. It’s been great to start a career here. You know being able to get residency programs the way that I have. The grassroots organizations like ArtLoveMagic, where I was able to get reactions to my work from hundreds of people who come to their events. These people weren’t collectors, they were just general people having fun and enjoying art. That helped a lot. It helped me know what people like and it helped me know how they’d respond.

Have you been able to quit your day job?

I don’t have a traditional day job, but I work at the Fort Works Art gallery and I get an hourly wage. Luckily, I don’t always have to be there in person. It’s part time.

That being said, to float how I am living, I can’t do it only with art. So to afford my life, I do design work. I have like four design jobs that I have to do right now. I also do commission work. They’ve been rising a bit recently. I actually have had some come through from Instagram – “The Swizz Beatz Affect.” He posted a piece and people from New York wanted my art. I was like, “Thanks, Swizz Beatz.”

You know it’s funny, because people saw that Swizz Beatz had posted my work and people were calling me. And I don’t get on Instagram like that, so people were calling me and I was like, “Well, I only got 500 followers.” I’m not very excitable. I tried not to be rude, but I was telling people, I don’t think it’s going to change my life or anything like that. Not that he cannot have that affect, but I have been doing this my whole life, so it’s cool that he posted. It probably helped me get in to SCOPE, which is cool.

"Looking Forward (Kelsey) - Riley Holloway This is the image Swizz Beatz shared on Instagram

“Looking Forward (Kelsey) – Riley Holloway
This is the image Swizz Beatz shared on Instagram

C’mon you’ve got to be a little bit excited. Swizz Beatz works with Kanye West and Jay Z. He’s a big deal.

Yeah! But I’m just not excitable. I just seem less excited than people on the outside. You know when people don’t know what you’re going through on a regular basis, then they can think, “Ooh! If Swizz had posted my work, I would have reacted this way.” But it’s not like that. It benefited me, so I am not knocking it. I just have a cool temperament about it. You know?

Well, you may not know this, but I did a story about Instagram changing the art world. So this is a new perspective for me.

Well, it is changing the art world. I think its introducing art to a younger audience. The commissions that I’ve gotten from Instagram have been from like 28-year-olds. It’s very cool and interesting that they’re buying. You know? Maybe they don’t even go into galleries. Maybe Instagram is where they see the art. They go to the hashtag gallery.

Riley, when did you first start to call yourself an artist?

When people started interviewing me (laughs) and asking me if I was an artist. You know, at the time I wasn’t selling anything and that’s what I thought an artist was. I was doing anatomy and I didn’t have a title for myself. I wasn’t planning on doing anything with my sketch book. I had this sketchbook filled with my drawings and thoughts. And the sketchbook was supposed to be just for me. To this day I still won’t sell it, but I got people trying to buy it. They want the whole thing, but I’m like, ‘no.’ That’s my whole thoughts (laughs). Who buys a journal? It’s interesting. My daughter will probably end up with it.

I guess I started taking myself seriously as an artist after the Fairmont [Hotel] Residency. Before that, the whole time I was making artwork, it wasn’t even a thought.

Topic - Riley Holloway

Topic – Riley Holloway

Are you creatively satisfied?

Yeah. There’s been a couple times where I felt like I might have conformed to the business. And I can always tell early on [if I am doing something too crazy] and I’ve abandoned an approach I was taking, because I felt like I was doing what I was doing for somebody else. The only time you’re supposed to do that though is for a cause, or for a commission. I feel. So, yeah I’m satisfied. I just keep focused.

What have you had to give or sacrifice to pursue your art?

Nothing. I’ve only gained. That I can honestly say. For me, art has not been a thing where I have to give up anything. Not financially or anything. I mean, its $40 to build the [panel]. And depending where you get the paints, it’s not asking much. So did I give up something? Nah. I feel like when I was doing other things, that I was giving up this. This has only added to my life. It gave me things that I wouldn’t have had. Even this place [his studio]. I wouldn’t have had this and I really like this place. (laughs) This is like my little place for Zen, so yeah no I haven’t given up anything.

Interview has been edited for clarity and brevity.

  • beth ritter-perry

    I heard this interview this morning and was compelled to check him out. Beautiful work! Godspeed in all of your endeavors!!!