White Bear Lake Artist Captures Notable Rock Icons’ Attention With Colorful Portraits

Taylor Rae Hillestad captures 1970s and ’80s music icons on canvas.

It’s not every day you can say you’ve met a famous rock icon, let alone more than one. But so far painter Taylor Rae Hillestad can list Boy George, John Oates of Hall and Oates, Steve Hackett of Genesis, Kandace Springs, and Jon Anderson and the band Yes as music artists she’s met in person—and she hopes the list will keep growing.   

Hillestad, who grew up in White Bear Lake, has long been comfortable with a pencil and paintbrush thanks to several artistic influences in her life. “My grandpa was an artist and he taught me how to draw,” the young artist says. “I had that creative gene in my family.”

Pat Benicasa, one of Hillestad’s high school teachers, further inspired her to pursue art.

“I think I first learned how to paint from her,” Hillestad says. “She just noticed something a little different about me compared to the other students, just how passionate I was, and she urged me to go to art college.”

So Hillestad attended Kansas City Art Institute in Missouri, where she obtained a bachelor of fine arts in graphic design. Graduating in 2014, she worked as a graphic designer, and that same year took painting classes and began painting her one-of-a-kind musician portraits.

“John Oates from Hall and Oates had an album cover contest, and I wanted to paint him and do something different,” she explains. Though she didn’t win the competition, her work generated a lot of attention. “I ended up getting connected with [Hall and Oates] just by posting my stuff online. Next thing you know, I was meeting John Oates in Vegas.”

Hillestad has several completed portraits in her collection. “This is David Gilmour from Pink Floyd. And I’m doing Duran Duran, just kind of for fun,” she says. Portraits of Pharrell, Chromeo and Sam Smith also line her walls. “I’m really inspired by musicians,” she says. “They give you a good excuse to go crazy and abstract.”

A portrait usually takes two weeks to a month to complete. “Mostly I do older musicians from the ’70s and ’80s; that’s what inspires me the most,” Hillestad says. Prints of her work are for sale on her website, ranging from $75 to $200, depending on the size. Hillestad also does custom paintings starting at $300.

Her paintings are her way of honoring artists whose music has inspired so many fans. Through painting several portraits of Steve Hackett of Genesis she has become friendly with the guitarist and attended his concerts in Philadelphia and Los Angeles.

"I love Taylor's artwork,” Hackett says. “It is beautifully colorful, and she wonderfully portrays both physical appearance and personality of everyone she paints. Taylor is an incredibly talented and inspired artist.”

Hillestad hopes to display her work in her own gallery someday. “One day I’m going to paint Roger Waters; he was in Pink Floyd,” Hillestad says. “And I want to paint John Legend sometime.”

For anyone who wants to pursue their passion, Hillestad wholeheartedly encourages people to take that first step. “Follow your dreams, never doubt yourself; you can always prove yourself wrong,” she says. “Do what you like and [life] will be so enjoyable.”