By Claudie Benjamin

Jason Oliva has been creating paintings professionally for twenty-three years. He has spent the last six years working from Broadway on the Upper West Side.

Many artists take inspiration from a memory, a conversation, a passage from a book, the image of an animal, nature, or an object. Jason seems to take from all of the above and more. He doesn’t paint abstracts; he likes things to be things. After speaking with Jason, it is obvious that his sphere of interest remains huge. Yes, he’s moved by his father’s collection of Buddha sculptures, the result of growing up in a house filled with Japanese décor; filled with awe linked to space exploration, art history, and literature; awestruck by the majesty of lions and amused by the unlikely grace of giraffes and the quirkiness of the Zebra’s stripes. “I never repeat a painted image.” If he paints a lion, “that’s the best lion I painted at the time, and life is too short if you want to paint everything under the sun,” he explains that collectors have access to the painted images through the hundreds of hand-painted, limited edition works on Arches paper of that lion and hundreds of other images that appeared in his “sold paintings” but never alters the design or background. Throughout his 20+ years-long career, he has accepted many painting commissions, understanding that the meanings and associations with particular images may resonate in different ways from the meaning they have for him. One very popular image of a ladder, for example, “relates directly to something he read regarding when you get older, and there is less time left in life. If you are going to metaphorically climb a ladder, you better make sure it’s up against the right wall. So he painted a ladder as a reminder of that wisdom. Jason believes it is important to focus on people and especially individuals. He seems to measure success by how many new collectors he achieves in a given year as opposed to dollars, although he admits they do go hand in hand and strengthen a long career.

Ever amazed at the fortunate twists of life, Jason never imagined how his career has evolved, encouraging and supporting his approach to painting and achieving ongoing success. Yes, many people buy his paintings that Jason, as opposed to art, seems to constantly refer to them as “gifts.” More specifically, he creates these works for people to gift themselves or others. People celebrate their successes, new family members etc., and they like to buy and gift paintings and art as totems to remind them of those moments in life. The term “gift” takes pretension out of the art equation. Jason welcomes the very positive idea that he makes a living making gifts. He likes the aspect of commissions where a collector has an idea he’s never painted before. A recent example asked by one of his over 1200 collectors was for a painting of the vintage carousel in Asbury Park, NJ. Jason has traveled widely and sold paintings in over 30 countries and almost all 50 States. It becomes evident his overriding career goal is to sell art in every country and every state, and he jokingly complains about how patient he has been waiting on someone in West Virginia to purchase from him.

It’s Jason’s business approach that meshes with his abilities as a painter that has brought him success. Jason’s mother encouraged her son to go to business school as a backup to his interest in painting and drawing. Jason says my mother would tell me I already know how I like to paint, so go develop interests that would lead to what to paint.” It turns out he enjoyed college, earning a degree in finance from George University in Washington DC. He then worked for 12 years as an Options floor trader “yelling and screaming” as a member of The American Stock Exchange on Wall Street.

During this time, he was also working on his art and exhibiting work at ultra-cool places like John Allen’s Men’s Clubs, The Luna Lounge, and CGGB’s 313 Gallery. His studio during those years was in Battery Park, then after time in Europe, back to Tribeca. Jason currently lives and works on the Upper West Side in (what is now) the Apple Bank building. He also resides there with his wife, two stepchildren, and a dog they rescued post-Covid. The duplex, with outdoor space, offers an impressive long gallery for exhibiting paintings. He says he loves having a home studio where there is no need to go out somewhere to make art. “Someone once said, ‘If you want the muse to visit, you need to be there in your studio with all your tools handy,’” working from home provides that environment.

Jason was drawn to the city from the time he was a teenager. His spontaneity, enthusiasm, and outgoing personality helped him get to know some luminaries of the art and music world going all the way back to the late eighties. He was always inspired by the NYC artist-as-businessman model of the time, think Andy Warhol, Keith Haring, and then-NYC resident Mick Jagger. It was when Keith Haring was asked to provide art for a Chateau Mouton Rothschild wine label back in the 80’s that inspired him to want to create his own wine so that he could adorn the labels with his own artwork.

With a Keith Haring “ignore the gatekeepers” attitude, Jason joined forces with a Stellenbosch, South African wine producer, and Jason Oliva Wine was born in 2011. Sold in bottles with labels featuring Jason’s painting images on the label, they are well on their way to releasing twenty-six vintages (wine speak for the year a bottle is produced), one for every letter of the alphabet: (A)stronaut, (O)ctopus, (M)oose etc. the wine can be purchased online.

And beyond the South African connection, Jason’s baseball image was displayed at Bloomingdale’s flagship store in New York by the Ralph Lauren company, a place special to Jason because his mother worked at Bloomingdales for Clinique. This eventually led to Ralph Lauren commissioning eight images from Jason to be reproduced and used to decorate their children’s boutiques globally. Something Jason is particularly proud of, especially how it ties to his goal to have art in all 196 countries.

In what seems like an endless series of fortuitous moments in his long career, one that I particularly enjoyed was how two of Jason’s Astronaut “gifts” the Astronaut wine and his Astronaut t-shirt, wound up being given to famed Astronaut Scott Kelly, prior to his historic Year in space Mission in 2016. Scott Kelly honored Jason by bringing the Astronaut t-shirt up to the International space station, where it spent 342 days orbiting the Earth 5,440 times and traveled 17,500 mph for over 143,000 miles! This was all described on the Certificate of Authenticity NASA sent Jason when Scott Kelly returned the shirt autographed.

Follow these links if you are interested in learning more about his art, wine, shirts, and his time spent on the Upper West Side. In addition, if you are from West Virginia, Jason will offer you a discount!

– Profile Photo image credit Joe Johnston


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