Artist and creative director Donald Robertson has built an illustrious career out of capturing the Zeitgeist. His paintings pair fast and furious brush strokes of exuberant colour with a laser-sharp focus on the intersection of fashion and pop culture. A master of motif, Robertson generates graphic signatures riff on dripping lips, sardonic designer logos, galloping horses and stylized cowboys, and his work has an #iykyk vibe that conjures a milieu of fashion VIPs, effortless affluence and iconic Americana.

“It’s almost like I’m art paparazzi: I like to capture something that’s happening right now,” says Robertson, a prolific social media poster who has collaborated with prestigious fashion and beauty brands, upscale department stores and boutiques, and top newsstand magazines on a range of endeavours, from lipsticks and capsule collections to pop-ups.

Last year, Robertson’s paparazzi paintings included besties/Olympic commentators Snoop Dogg and Martha Stewart, athlete/tabloid regular Travis Kelce, attention-getting pop star Harry Styles, plus a mix of royals — of both the Windsor and the Hamptons sort. Collectors like Beyoncé (or the fans who snap up his work practically as soon as it appears on his Instagram) can’t get enough of it, and neither can the artist himself, a Canadian who now lives in Dallas, after stints in Toronto, New York, Korea, Japan,China and Los Angeles.

“I never wanted to be a starving artist,”notes Robertson, who started his career in the late 1980s after dropping out of Toronto’s Ontario College of Art to work with then up-and-coming MAC Cosmetics.

At MAC, the young artist developed creative concepts that led to his love of iconography. “That’s where the lips came from,” he says of the glam motif he has slapped on countless canvases — a car, even a building exterior in Nashville.

It also honed his instinct for finding the next new thing. “I got my green card, moved to New York and started in publishing next— and that’s where the celebrity obsession came from. My generation, we were putting celebrities on magazine covers, which was, at the time, unthinkable,” says the father of five and a former creative director at top U.S. fashion magazines like Marie Claire, Glamour and Cosmopolitan.

“I was in publishing for a long time and I got addicted to news leads. It was just something that was drilled into us. If something was news, newsworthy or new, it would hit. And that’s always been something that I’ve liked to incorporate into my art,” he explains.

Recently, that included chronicling pop culture’s unofficial Family of the Year. It all began with a painting of Donna Kelce (mother of football and podcast starsTravis and Jason Kelce) as she spectated at Superbowl LVII, where her two sons played on opposing teams.

“I remember thinking at the time, This woman is incredible. And I painted her on a cereal box and called it ‘Special K.’ It was just something that captured a moment.She was new to my people, my followers, but likeable…so I painted her. Then she immediately reached out to get it. The next thing you know, she sent me a picture of her holding the box,” says Robertson.

This social media connection continued through the year. “I sort of befriended the family. And when Jason was made [a finalist in People magazine’s] Sexiest Man Alive, they called me to do a painting of him to tease him; it created this whole news thing. Then Taylor Swift showed up and it was just “Game on.” It just exploded.So, it was a series of newsworthy things that became this really, really fun year of documenting the craziness that was the Kelce family and the Swifts.”

Robertson’s visual hot takes have earned him 227,000 Instagram followers, many of whom are eager to snap up his art, much of which is made quickly and sells quickly.

This immediacy — and the direct line to tastemakers, collectors and fans — is something Robertson has valued ever since his oldest daughter convinced him to grab an iPhone and venture onto Instagram.

“Next thing you know, I was having. back-and-forths with Carine Roitfeld and working with Colette,” recalls Robertson, referring, respectively, to the influential former editor-in-chief of Vogue Paris and the chic Parisian boutique.

“Instagram made the world very small and very accessible. It was wonderful andI got addicted to that community. It’s changed and become a big giant beast, but there’s still community. I’m like an old dad and Marc Jacobs is popping onto myInstagram and liking stuff. “When I was in [print] magazines, [that] would’ve been virtually impossible.”

While the artist is far from obscure now — you know you’ve arrived when Assouline publishes an eponymous tome on your life and work — Robertson relishes the gatekeeping that social media dismantled.“When I was young and hustling, I had a pain-in-the-ass portfolio that I had to drag to Europe. I had letters of introduction thatI had to hide when I was going through customs. And then people would cancel meetings…and by the time you finally got to meet with somebody, you were just so frustrated if it didn’t go well. Those days are gone. It’s been a great equalizer and it’s been very exciting,” says the artist who uses social media to showcase, and solicit, new work. (“I’m paying for college tuition with this stuff,” he quips.)

Over the years, Robertson’s self-diagnosed “trend FOMO” has driven him across America and Asia where he has designed global marketing campaigns— (he was senior vice president creative director at Estée Lauder for several years),collaborated with renowned artists and brands and honed his art. But Dallas maybe where he takes a breather…at least for a little while.

Social media is now his favoured career conduit. “It’s a way of doing my corporate job and incorporating my art at the same time. It’s a nice overlap. Also, it’s really hard to hustle content for Instagram. But if you can paint, it makes it so much easier.I don’t have to go to exotic locations to get pictures. I can just paint them. I can literally create content all day long in my studio,” he explains.

Of course, the next paintable meme always beckons. As an example, Robertson recounts the story behind his Internet-famous Snoop and Martha Stewart series.

“When Snoop Dogg showed up at the [2024 Paris Summer] Olympics, at the equestrian event, in that tuxedo suit, I was just like, Where’s my paint? Where’s my paint? Maybe I’ll just do the Olympic circles as smoke rings. Oh my God, that painting sold so fast. It was unbelievable.

“Then I did a picture of Martha withSnoop: the ultimate odd couple. It was just so sweet,” says Robertson, who in December posted an Instagram photo of Stewart holding one of his sold-out Snoop paintings.

After a four-decade-long career, Robertson knows to amplify a news hook when he sees one. “That’s the kind of thing that creates community through your art. But it also makes something irresistible. You know whatI mean?

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By Yuki Hayashi — *This article originally appeared in Insight: The Art Of Living Magazine – The Connection Issue.