How Jason Farley is doing what he loves

It is a warm Saturday in April that I lean back in an office chair in an artist’s studio. The studio is located in his apartment where the living room would have been, if not lined by blank canvases. Today, I sit across from an incomplete oil painting placed beside a cherry red drawer of paints.

The painting is surreal: the faces of three different women diverge from one body, and behind them is a white horse mid-step with sections of blues, creams and maroon to create a vibrant backdrop.

The artist of this work, Jason Farley, is a portraiture surrealist artist living in Pilsen, Chicago. But Farley’s creative journey began far before becoming a part of Chicago’s cultural scene. 

Jason Farley lives in Pilsen, Chicago, and paints surreal portraits in his at-home studio. Photo by Sam
Freeman.

Raised in Northwest Indiana, Farley spent his Sundays watching cartoons with his brother while his father went to work in the steel industry. Farley’s mom suggested that, since he’s spending so much time in front of the TV, he should draw the characters. 

In school, Farley quickly became known as the kid who draws. From cartoons to celebrities, Farley was regularly picking up a pencil and paper to sketch, in addition to his many academic and athletic commitments. He continued to draw with hopes to attend art school but lacked the financial resources to do so. 

In 1998, Farley joined the Army to receive money for his schooling. He worked five days a week from 6 a.m. to 5 p.m., with the weekends and holidays off. During his deployment, Farley began to travel and experience the world, from surfing in the clear waters of Hawaii to wandering the streets of Japan. Nature had become an integral part of Farley’s life. 

“I mean, just seeing different nature and being out and traveling out in the middle of like, these places in the middle of nowhere. Just seeing my surroundings. I mean, that’s what I think that’s what inspires a lot of things: beauty,” said Farley. 

Many of Farley’s recent paintings are sold on Artist Replete, an online gallery that sells select works from
Chicagoan artists. Photo by Sam Freeman.

Farley’s art has evolved alongside his individual journey. While he attended the American Academy of Art, he was simultaneously working at an advertising agency, where he learned about the business side of art, including copyright laws and licensing privileges. 

Today, Farley is self-employed, and he spends most of his days painting alone. He draws from his own thoughts and ideas instead of collaborating with others, like he did at the advertising agency. According to the artist, it takes a specific type of person to be left alone with their thoughts. 

But that doesn’t seem to be a problem for Farley. 

“He’s a very serious person. So when he’s working, nothing can distract him, like he will stay in for weekends on end just to paint. And I think it shows in his work,” said Samantha DeCarlo, a Chicagoan artist and friend of Farley. 

Jason Farley uses digital references to create his paintings. Photo by Sam Freeman.

For a while, Farley’s work mirrored the pop culture movement of the 1950s – because that’s what sold. Now, he paints surreal portraits, such as the one currently propped up on an easel in his studio. The work is part of a larger series that he feels truly represents his artistic capabilities and his interests as an artist. 

“This—” he said, motioning toward his work, “—is what I want to do.” 

According to Farley, oil paints are forgiving, which allows him to go over the same color several times to
perfect the tone. Photo by Sam Freeman.

The piece he’s working on has taken him over a month already. Part of that is because he’s precise with his work, layering oils on top of oils to achieve the perfect tone; and part of it is because he’s working on other projects, such as illustration projects for hotels and restaurants. Regardless, his commitment to the craft is undeniable. 

“Art is life. This is not just a job for me,” said Farley.  

Farley uses a lot of the techniques that he learned from art school, including the golden triangle, which
draws the viewer’s eye to the center of the painting. Photo by Sam Freeman.

Art, nature and the beauty of the world provide him with an escape, and that’s exactly what he hopes to achieve through his art: to create an avenue for people to get lost in. 

As I sat there, looking at his art, the remainder of my questions suddenly seemed trivial and insignificant. Instead, I allow my eye to wander the depth and complexities of his work. I allow myself to escape within it.

Header image by Mei Harter