How Greg Simmons’ Crate Challenge Paintings Made Him an Instant Star

After making an Instagram account during the pandemic, Simmons received a flood of attention when his Crate Challenge paints went viral.

Artist Greg Simmons in his studio. Courtesy of Greg Simmons

Towards the end of a chaotic and thoroughly transformative summer, for a brief moment in time, nobody with a smartphone could look away from the Crate Challenge, an irresistible prompt to scale milk crates arranged in a pyramid without falling off. The game led to daring feats of bravery and harrowing injuries, and the imagery became just as instantly indelible: quavering bodies poised on unstable bearings or else flying through the air, defeated. Greg Simmons, a painter based in Ridgewood, was instantly captivated by the challenge and decided to try to capture the spirit of the game on canvas. The results have earned him thousands of new Instagram followers, a flurry of print sales and a rush of gallery interest.

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‘Striving 4 Prosperity’ by Greg Simmons. Courtesy of Greg Simmons

It’s a rare thing when a cultural phenomenon is captured so perfectly, but Simmons had logged years of work leading up to this moment. “I’ve been painting since I was a kid,” Simmons told Observer. “I’ve always liked to look at things. I like doing realistic things, things I see in front of me. But once I started becoming a skateboarder I was definitely fixated on skate culture, and that’s a lot of what my subject base would be.”

When Simmons started skating in the 90s it wasn’t at all popular, but his fascination with the sport was undeterred. “A lot of the black skaters just really captivated my mind because they just seemed cool, they just really gave me confidence,” Simmons said. “Their features made me wanna draw them.” Simmons kept up his art practice over the years, and made his Instagram account during the pandemic. He also currently works with the Harold Hunter Foundation, which provides resources and opportunities for Black and brown skaters in New York City. 

Another of the artist’s Crate Challenge paintings. Courtesy of Greg Simmons

After finding out about the Crate Challenge on WorldStarHipHop, Simmons knocked out two paintings on Monday, August 23rd, mocked up some prints, and posted the images on Instagram. The reaction was instantaneous. “In one day it was like 1K in sales,” Simmons said. “And I was underselling myself to the point where my friend who’s in the art world, she DM’d me like ‘take those prints down;’ like scolding me almost, because I really was underselling them. But in just one day my Instagram just went from me following like maybe 300 people to having a few thousand followers, and some people with some credibility who I really needed to know.”

I reached Simmons in the direct aftermath of Hurricane Ida; he had just helped a cousin salvage some of her belongings after the roof caved in at her home in Brooklyn. Despite the random act of destruction, his mood was unflappably optimistic due to the response to his art.

“I was just very grateful to hear people’s feedback, and I was taken aback by the outreach of love and comments,” Simmons said. “People were saying it should go in the MoMA. Highsnobiety ended up reposting it and they said it might as well go in the National Gallery of Art. It was at that moment I realized that I should probably prioritize taking the art more seriously than I have.” 

How Greg Simmons’ Crate Challenge Paintings Made Him an Instant Star