Makeup artist and entrepreneur Jillian Dempsey talks about her career, personal style and what she likes best about her Maine life.
If you ever sit next to Jillian Dempsey on an airplane, feel free to ask her for makeup tips. “I can talk beauty to you until you tell me to stop,” Dempsey says. “I will talk to anyone.” The makeup artist and owner of her own beauty line might even be departing from the Portland jetport; she and her husband, actor Patrick Dempsey, have a house in Southern Maine.
Dempsey, 53, has been working in the beauty business for her entire career. “I’ve been very attracted to the beauty business since I was very small,” she says. She’s calling from Los Angeles, having already gotten in her summer visit to Maine. “I started out with crayons and drawing little pictures of dolls.” By the time she was a senior in high school, Dempsey was selling makeup from a private line to her classmates in Los Angeles. “Everybody wanted me to cut their hair and do their makeup,” she says. She went on to beauty school in Los Angeles and was cutting hair when she met her future husband in the mid-1990s (he came in for a trim, she told Good Housekeeping).
But neither her curiosity or excitement about her career has abated. “I still go out makeup shopping,” she says. “It’s the word artist that makes me get up every day and explore options.” She sculpts in her spare time and makes rose gold jewelry as well. Julia Roberts wears her necklaces, as does Kristen Stewart. Both actresses have also been clients of her work as make-up artist for years—that smokey eye on the Stewart’s dramatic cover of Vanity Fair this month? Dempsey created it. She’s worked with a fleet of other well-known names, from Jennifer Lawrence to Kirsten Dunst to Rachel Weisz. Not to mention her husband, who she works with regularly on advertising campaigns, including one for Tag Heuer that debuted this spring.
“Milla Jovovich I met when she was 16 years old,” Dempsey says. “I have been fortunate to work with the loveliest of women.”
But when Dempsey started her eponymous makeup line in 2015 she intended to reach far beyond the movie star community. “I am really interested in serving and providing makeup tips to everyone,” she says. “I don’t think of anyone in terms of their celebrity and fame.”Her ideal client might be someone a lot like her, a busy mother (she and Patrick have three children, Tallula, 17, and twins Darby and Sullivan, 12) who wants to use organic products on her skin, loves to get made up for special events, but is equally happy not made up. “I love being makeup free,” she says. She feels most beautiful “when I’m looking at my kids and laughing at my kids. At the way they are super silly and natural.” As busy as she is in her career, she aims to give her family her focus. “I would hate for them to remember me as ‘in a mirror doing your makeup.’” That’s part of her motivation to make the products she does. “I think that is why I like to do everything on the vanity front as condensed and fast as possible. I call it ‘lazy girl makeup.’”
“I do my makeup in five minutes in my car,” she says. “I am using two hands to drive but at the stop signs, I am putting on my lip balm (a must). To me it is all about your skin.”
Her first products were an eyeliner and a line of lid tints in five colors, organically made and intended to be finger friendly. “I wanted to do something that was like a balm for my eyes.” Then she brought out a cheek tint and after that, what she calls a “hero product,” a mini-fan brush that can be washed and is cruelty free (Dempsey advocates for animals and has a small “farm” of her own in Los Angeles, with pets ranging from dogs to donkeys.)
She’s been regularly debuting new products in the line, the most recent of which, the 24 karat Gold Bar, has attracted a lot of Internet attention since it came out in December 2018. (It doesn’t hurt to have online demos from Patrick Dempsey himself, or shots of someone like Stewart getting sculpted by the Japanese-made device.) It’s a $195 gizmo that uses a battery to massage and contour the face. Or the neck. As she puts it bluntly: “If you feel like you have a gobbler under your chin,” this can help. “I flew to Tokyo multiple times to meet with them,” she said of the Japanese manufacturer, who used one of her rose gold bracelets as they refined their choice of metals. “I use it before every appearance,” she says. “I use it on all my clients.” It’s a preparatory step before beginning to paint a face, and is useful for integrating moisturizer into the skin. “It’s like going to a gym for your face,” she says.
Wife and husband are both athletic. She surfs, he drives race cars and has been known to do some boxing. She’s a beachy sort used to a warmer ocean experience and Maine doesn’t always deliver on that. “I have to say, I was impressed the last time I was in Maine,” she says. “I actually went swimming in the ocean.” It was at Goose Rocks Beach, she says, and for once, the temperatures were refreshing rather than freezing. “I gravitate toward the summer months,” she says, laughing. “But it is all so beautiful. And my husband loves it so much.”
Her husband makes more regular trips to the state, because of his work with the Dempsey Center for cancer patients and their loved ones. He and his sisters established the center in their native Lewiston in 2008 in honor of his mother Amanda, who died in 2014 after fighting cancer for nearly two decades. “Patrick is on his way there now,” Dempsey says. The couple and all of their children had just attended the premiere of a movie the former Grey’s Anatomy star executive produced, The Art of Racing in the Rain, and he’d arranged a special screening of the film in Boston to benefit the Dempsey Center.
But they’ll both be back to Maine together this month, for the annual Dempsey Challenge, the run, walk, cycle fundraiser for the Dempsey Center (Sept. 28–29). “I am very proud of him,” she says. “Aside from being the eye candy for a lot of women—and I am fine with that—it is deeper than just that with Patrick.” He loved his mother so much, she says, and what he and his family have done to honor her memory continues to impress her. “It is designed not for cancer, it is designed for people, people that are in need, who need guidance and advice and are scared,” she says. “What he has done has just been mind blowing.” Is she going to ride in the Dempsey Challenge? “Absolutely,” she says. “It’s a real mission for us.”
So is her mission of raising children who feel like they can express themselves creatively, and feel comfortable in their own skin (and, she says, “have nice manners”). “We are in this time and space where the new generation, they are growing up in a much faster-paced world with a lot of social media.” And carefully curated images. She considers it essential to make the difference between image and reality clear to this generation. “Really, internally, if you feel good about yourself, it reflects through the radiance of your smile,” she says. And while it’s fun to play with different images, “you have to take the makeup off at the end of the day.”
Mary Pols is the editor of Maine Women Magazine. She interviewed Patrick Dempsey for Maine Voices Live in 2018.