Gregory Siff: The Art Of Paying Attention
Gregory Siff still remembers hearing the Mister Softee jingle from blocks away in Brooklyn. He’d chase the truck down the street, anticipation building until he could get close enough to see the colorful menu and decide what to order. That childhood ritual still finds its way into his paintings. It reminds him to keep a child’s sense of wonder and to be grateful for what a day brings. When he began showing his work and people started coming to see it, he felt a kinship with the man behind the window. “I felt more and more like the Ice Cream Man,” he says. “Everyone was coming to catch the vibe.”
After two decades of painting in Los Angeles, the artist, a 2026 Men Of The Year honoree for Deluxe Version Magazine, is starting a new studio in Las Vegas. The move has changed how he sees a familiar image in his work. He’s long painted dice that add up to seven in honor of his father, a restaurateur and avid craps player who lived in Las Vegas. The dice now mark the place Siff calls home, too. Painting them makes him feel closer to his father.
The title painting of his exhibition To Understand Time changed how Siff thinks about a day’s work. After a long day of painting, he was lying in bed when he exhaled the words “today in my eyes.” He heard them as a message from God and recognized that their initials spelled TIME. He describes looking down at his paint-marked hands and reading the day in the paint that landed there. It was a way to pay attention to the moment he was in, even when he felt the urge to force the next one.
“The sky and your heart have a much clearer vision than the mind.” — Gregory Siff
Painting live on the runway for Pyer Moss gave Siff a different lesson in staying present. The garments moved under his brush as the models walked. He recalls misspelling words and seeing lines run off a jacket and onto a pair of pants. In the moment, they felt like mistakes. When he saw the photograph in The New York Times Style section, the marks looked exactly right to him. “It takes more paint and play to make it yours,” he says.
For his 2026 exhibition Find Your Star at TF Gallery in Dallas, Siff tipped his hat to the Lone Star State. The title also evokes a moment he describes as the instant someone meets your eyes and everything makes sense. In the triptych In the Company of Icons (The Constellation of Dallas), those ideas come together in what he describes as a constellation of people and prayers across time and space.
Siff has committed to making something every day and sharing it, whether it’s a drawing, a painting, a mural or a poem. The habit keeps him ready to work and gives him a way to draw attention to causes he cares about. Among them is Arnold Schwarzenegger’s After-School All-Stars, whose programs give young people in underserved communities a safe place to spend the hours after school. For Siff, the chance to help those kids feel inspired is one of the most fulfilling things his work can do.
The 2026 Men Of The Year recognition from Deluxe Version Magazine comes after a year that taught Siff to slow down and ask for guidance. He’s learning to give up the reflex to say, “I’m the Man! I got this!” As he starts work in Las Vegas, he wants to “let Jesus lead my brush and path.”
