In a cozy St. Paul apartment filled with art and stacks of the New York Times and New Yorker magazines, 96-year-old Doris Simonett sits surrounded by portraits that tell the story of her life. She wears chunky black-framed glasses, funky pants, and a loose black shirt, her face lit up with a big smile as she discusses the artwork covering her walls.

Among the collection are portraits of Doris and her late husband, former Minnesota Supreme Court Associate Justice John E. Simonett, painted during a European trip. There's one of her father that she created herself. But the centerpiece is a recent painted portrait of Doris, completed last fall by classically trained Italian fresco painter Charles Kapsner, an old friend from Little Falls, Minnesota.

"What's really most important is catching the essence of that person," Kapsner explains. "In the case of Doris and myself, we had this long history together."

Kapsner acknowledges that portraiture presents unique challenges. "People might see themselves very differently than what the artist does, even if you have an incredible photograph," he notes.

The portrait of Doris came about when her five children commissioned it as a celebration of their mother. Initially, Kapsner painted her blouse black, but it seemed too somber. "Then mom thought about it, and she said 'Let's change the color,'" recalls her daughter, Martha Simonett. The black became lavender.

Doris admits she was surprised by her likeness. "I was kind of shocked. I don't think of myself as having all those wrinkles and stuff. I think of myself as I used to be, you know?"

This sentiment touches on the profound nature of portraiture. While a picture may be worth a thousand words, a portrait can bare one's soul. The most famous portrait of all time, the Mona Lisa, commands its own room at the Louvre. People commission portraits for weddings and funerals, for friends, family, and even pets. There are portraits of politicians, judges, and CEOs. Artist Kehinde Wiley painted former President Barack Obama's official portrait, while President Donald Trump once demanded that a portrait of him in the Colorado State Capitol be removed because he felt it distorted his image.

In the California Building in northeast Minneapolis, artist Suzann Beck's studio is a shrine to portraiture. On a steamy July afternoon, prints from a recent funeral portrait commission are scattered near framed portraits of a Black woman with a flower in her hair and a delicate blue-eyed cat. Beck is busy creating a live portrait of Sarah Joy Bruce, a professional cellist.

"The strings are always the hardest," Beck says, concentrating as she looks at Bruce, switches tools, and draws a few more lines with charcoal. At the front of her studio sits a nearly finished portrait of Mojo Coffee Gallery owner Marko Fields with his guitar.

Beck, who ended a 30-year career in graphic design and marketing to pursue her passion, explains her longtime attraction to painting people. "I guess there was a painter inside screaming to get out because I would go to the museums and see the European portraits, and I would always get this urge to go home and do it myself."

Most of Beck's work comes through commissions. "When the person commissioning the portrait knows the subject, I find that likeness or accuracy is the most important thing," she explains. "If you're doing a portrait that is going to have public appeal, I think narrative is the asset that's most important. I have a high degree of accuracy, and so when that's important, people come to me."

Accuracy matters, but so does flattering the subject, Beck notes.

In Savage, Minnesota, artists Jon Swihart and Kimberly Merrill have found a quieter lifestyle after moving from Los Angeles in late 2022. Gone are the epic monthly artist community potlucks they hosted in their Santa Monica backyard. Now, the most prominent sound is cars whizzing down mostly empty streets.

Swihart, a California native, stumbled into portraiture accidentally. He began painting portraits in the late 1970s and early 1980s but kept it mostly quiet because portraiture is often associated with "selling out." However, the commissions kept coming, and today his star-studded client list includes actor Clint Eastwood, former U.S. Supreme Court Associate Justice Sandra Day O'Connor, and architect Frank Gehry.

"Especially when I've painted famous people, I realize they're just as self-conscious or wanting approval as I am," Swihart reveals. "I painted Walter Cronkite years ago, and when I was working on it, his secretary called me and was talking really quietly, and she said: 'You know, Walter asked if you could tame his eyebrows.' I was like, 'That's what he's self-conscious about!'"

For corporate portraits, such as a recent painting of the FedEx CEO, Swihart notes the different approach required. "It's about painting somebody the way people see them, the way they imagine them to be. I have to make them look confident. I can't paint the vulnerable side of them. People don't want to see that."

In a newly remodeled basement studio in south Minneapolis, artist Jonathan Aller dabs bits of orange paint onto a portrait he's creating. Aller grew up in Miami, with family roots in Chile and Brazil. As a child, he dreamed of becoming a Disney animator, but when the industry shifted toward computer animation, he changed course and studied in Florence, Italy, for three years, learning from masters of European art history. There he met his Minnesota-born wife, and they returned together to start a family. Aller also holds a Master of Fine Arts from the Minneapolis College of Art and Design.

"I'm drawn to portraits," he says. "There's something about a portrait, you know, through the eyes of a portrait of a sitter, that you can get so much from them."

He points to a portrait of a man sitting on a bed, his face hyper-realistic, eyes pointed downward, glasses on his face. In the painting, the subject's shoulders slump slightly, appearing somber, but a carpet with colorful dots and bright socks lift the mood of the piece.

"This was a guy I actually met through the city bus," Aller explains. "The more I talked to him, he told me he had Argentinian roots, and he just looks like, you know – we're both very light complexion but we're Latino, and I felt kind of this connection with him already."

Sometimes portraits are sparked by that sense of connection, but other times, it's simply about timing. At the Minneapolis College of Art and Design's annual art auction, recent Bachelor of Fine Arts graduate Wren Clinefelter, who uses they/them pronouns, drew three-minute sketches of anyone willing to pose during the busy evening event.

The atmosphere is much calmer on a July morning in their air-conditioned third-floor studio in south Minneapolis. Studio cat Wisty, a tabby, gently rubs against Clinefelter's legs. Rather than warming up by drawing portraits based on images from Pinterest ("the algorithm knows me," they joke), they start drawing the cat.

These warm-up sessions are crucial, especially for the live portraiture events Clinefelter has been exploring since graduating with a BFA in comic illustration.

"People would come stand behind me and watch me work," Clinefelter recalls. "That was something I had some experience with. In elementary school, people would be like: 'Can you draw me?' And then a crowd of people would gather around my desk. It was very surreal – it's like wow, I'm doing the same thing I was doing in third grade, but I'm getting paid to do it."

These Minnesota artists, from the 96-year-old subject to the recent graduate, demonstrate that portraiture remains a vital and evolving art form. Whether capturing the essence of a longtime friend, flattering a corporate executive, or connecting with a stranger met on public transit, each portrait tells a unique story while revealing universal truths about human nature and our desire to be seen and understood.