Post-post-colonial Jamaica, the pollution crisis in China, and the inked up working class of Ohio seem like unusual choices for an art show, and that’s the point.

A search for the unconventional has been a success, as the Richard J. Demato Gallery prepares for its last show of the summer, “Shattered Boundaries.” The desire to find something edgy has left curator Eve Gianni and gallery owner Mr. Demato with a multifaceted show in the small, two-story Main Street space.

Phillip Thomas, who will be in Sag Harbor for the show’s opening reception on Saturday, August 23, is a 33-year-old artist from Kingston, Jamaica. Mr. Demato was introduced to the young artist by local painter Eric Fischl.

Mr. Thomas received his bachelor of fine arts degree from the Edna Manley College of the Visual and Performing Arts in Jamaica, and then, after receiving a grant, traveled to the New York Academy of Art to work toward his master’s degree. Mr. Thomas graduated top of his class and was awarded a fellowship.

It was during that fellowship that Mr. Thomas began using his art to discuss and comment on the real issues and problems in his native Jamaica. “Jamaica has been marketed to the world as paradise, a place of bliss and sheer exotic splendor,” he wrote in an e-mail on Friday. “This bliss is no doubt an exotic gaze, the cast of the non-Jamaican looking in and having very strict expectations of the culture.” According to Mr. Thomas, this has resulted in the inability to see the person before the citizen, the habits before the culture.

This has inspired him over the years, and continues to in his most recent works. Many of his paintings show empty suits—headless, handless bodies in suits, stripping down a national “catch-phrase,” presenting civility intertwined with sociopolitical violence.

Mr. Thomas has used images of matadors to represent the dualism of beauty and violence that is so rife in his home country. His work, he said, often references English and Spanish cultures “through a kind of reversal.”

“Bullfighting, then, is used only as a metaphor to talk about a kind of ‘orchestrated violence,’” he continued. “This glorified iconic ‘death dance’ presents itself in Jamaica in various ways.” The Caribbean island is known for its pristine beaches and beautiful flora, but also for its gang violence and drug warfare.

Even his media represent the chasm between the reality and perceived image of his home. “In painting, the material has been so entrenched in the history of art that its material has developed a kind of iconic presence regardless of the type of image it executes,” he wrote. Mr. Thomas has used oil paints as a signifier, he said, but the combination of that with other media has resulted in “a kind of network of idiosyncrasies.”

Ohio artist Frank Oriti’s oil portrait series also shows a network of idiosyncrasies, but in a very different way. When he found himself working at a Cleveland steel mill after receiving his bachelor of fine arts degree, Mr. Oriti was inspired to create something real.

“Frank’s work is also very much shattering boundaries of what we perceive as beauty,” Ms. Gianni said. “Most people think beautiful people in beautiful circumstances—he’s painting middle America.” Mr. Oriti often uses the quasi-destitute as subjects for his portraits, embracing and detailing tattoos, facial hair and looks of despair.

Mr. Oriti’s portraits will also be on display at a show supported by the Richard J. Demato gallery in Jacksonville, Florida, next month. The tatted-up figures which punctuate the gray, washed-out backgrounds of the paintings will be on show in an exhibition titled “Get Real: New American Painting.”

“Years from now, when you look back, this is really what our society looks like,” Ms. Gianni said. “And in addition to it looking like this, it also feels like this. There are a lot of people who are kind of challenged right now,” she said. “And that, in another way, kind of shatters some boundaries.”

An opening reception for “Shattered Boundaries” will be held on Saturday, August 23, 2014, from 6:30 to 8:30 p.m. The Richard J. Demato Gallery is located at 90 Main Street in Sag Harbor. For more information call (631) 725-1161.