LAST NOVEMBER, Matt Held was slogging through a serious case of painter's block. He and his wife, Joelle, had just had their second child, Astrid, and he had left his job as a postwar art handler at Christie's to be a stay-at-home dad.

"Everything was going wrong; I was in this total upheaval," Held, 37, explains. In his closet-size studio off the family's living room, a small model of a human skeleton sits in the window, overlooking a quiet street in Brooklyn.

"I couldn't paint to save my life," he says. He strokes his left arm, which is imprinted with tattoos—a pinup-style woman clutching an anchor and a stack of building blocks spelling out his 5-year-old son's name, Otto.

But then, late last year, his wife updated her Facebook profile picture. She posed in an "angry face"—pursed lips, brunette hair in tangles, a finger jabbing at the viewer—and snapped a shot using iPhoto, a program on Apple's MacBook that takes photo-booth-like pictures with a tiny lens on the top edge of the laptop screen.

Using the photo as a reference, Held painted her portrait with oil on canvas. Something clicked. The painter's block was gone.

Held scoured his Facebook network for more inspiring portraits, and within two weeks he had painted five of his friends' profile pictures. In late December, Joelle Held, an assistant at a private-equity firm, created a Facebook group called "I'll have my Facebook portrait painted by Matt Held," which now has about 3,500 members from which Held can choose.

He has created 45 Facebook portraits so far, all for free, in exchange for permission to use the portraits as he likes. He has painted friends—including fathers from Otto's local school and one maudlin-looking fellow enveloped in a pair of giant headphones—and strangers, too, like Peter Downes, deputy director at the Brooklyn Museum. In his portrait, he's grinning in a elaborately decorated shirt.

"I make no qualms about doing this for networking," Held admits. His goal is to finish 200 portraits by 2010.

Whatever his practical concerns, Held can wax poetic on his chosen vocation as well. "Throughout history, artists have always, consciously or unconsciously, made statements that are representative of their time," he wrote on his blog, portraitpainted.blogspot.com, where he and his wife chronicle the project. "The Internet and technology in general have made so many more things accessible to the general public that used to be limited to people who existed in higher economic classes. Considering I bend towards socialism, this project allows me to embrace the idea that everyone should be painted and memorialized."

Painted portraiture, which became popular during the Renaissance, used to be reserved for the elite, Held explains, back in his Brooklyn apartment. "That lasted all the way up to the invention of the camera. Still, it was expensive to get your photo taken, up until the snapshot camera was invented."

Digital media, from iPhone snaps to professional photos taken on fancy digital cameras, not only has made portraiture cheap, it has also revived the art form, he says. And, sure, Facebook has something to do with that, by providing a space for people to play with the whole concept of a portrait.

"Everyone and their mother can literally take hundreds of pictures of just a slight turn of your face and you can put it up and people can view it," Held says.

But modern, online "portraiture" is fluid. Most of us are constantly tweaking our Internet personalities—changing up our favorite bands and books, scripting eloquent "status updates" and switching profile pictures according to our mood. But in every detail, there's a little more of our selves revealed. Adding or deleting Lolita from a list of favorite books, or becoming a fan of Rahm Emanuel, tells a little bit more of our story. And the various photos posted by us or others—from the awkward karaoke shot to the elementary school yearbook photos, with '80s laser lights in the background—reveal even more.

Held considers all these other online "selves" before he starts painting. He browses his subjects' Facebook pages—checking out their occupation and where they live, as well as looking through their photo albums, to cobble together, as best he can, a sense of who people really are. He chooses which profile picture he likes best—he favors "quirky" shots, he says. Props, like a giant wine glass or ice cream cone, help, too. In a way, he has the ability to immortalize a person's personality in a time when it is ever-changing.

One of his favorite portraits is of his friend Shawn, who is flashing a crooked-tooth mug, waving a lit cigarette and sporting a trucker hat emblazoned with the slogan "I Love Sluts." "That is totally him," Held says. "He is this caustic rockabilly, you know, the most amazing person you'll ever meet because he's so much fun to hang out with." (We'll take his word on that!) In another portrait, of a stranger, he chose a picture of her making a silly face, with her fingers turned in upside-down OK symbols. Later, when he met her in person, he found out she was a very serious person.

Online Immortals

Held doesn't plan on just being the "Facebook artist with a gimmick."

"I am a serious painter," he says. "All I do is sleep and dream art, and I know it drives my wife crazy because it's all I talk about. So I do want to make this last and make sure these are seen."

He studied at the Rocky Mountain College of Art and Design in Denver, where he was raised. When his mother was diagnosed with cancer, he dropped out of school and moved to Seattle to take care of her. He tried a quarter at Cornish College of the Arts, but the place wasn't really his style.

"There's all these thespians in the hall practicing their lines and quacking like ducks," Held says. "I hated it, just hated it." He met his wife in Seattle and, in April 2006, they moved to New York, where Held got a job as a handler at an Upper East Side gallery and then, later, at Christie's. "After her maternity leave, I decided to just stay home and try to be an artist, which was probably the best decision I've ever made," he says.

He wakes up every day at 4am to start painting, and works until 6, when he has to get Otto off to school. He picks it up again at 10am, after Astrid goes down for her nap, working on more than one painting at a time. He finishes about two to three portraits a week. He has only sold one, but hopes to sell more so he can buy his own studio.

"I could paint these Facebook portraits until I'm 80," he says. "I'd never have this artists block to deal with because I could just go on to one of my friends' profiles and find a picture of them."

He hopes to see his portraits in a gallery, where his paintings could become an artistic representation of a web-based community.

"I'm offering people a chance at immortality," Held says. He mentions the famous portrait Madame X, by John Singer Sargent. The 19th-century portrait of Virginie Avegno sits in the Metropolitan Museum of Art.

"The layman doesn't know anything about Madame X, but you see this painting of her and it's just beautiful. So she will always be remembered. We're still wondering, after all this time, who was she in real life?"

Some of us wonder the same thing when we browse pictures on Facebook, aren't we?

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