GEORGE CONDO Though best known for his fiercely wacky portraits, the American artist George Condo is as much a portraitist as he is an abstract expressionist. “I love the idea of two incompatible worlds brought together—opposing forces harmonically melded,” he says. When he met Chastain, his plan was to create two artworks—and cast her not as their subject but as a character in them. “I wanted Jessica to become part of the painting and then appear to come off it, as if she were breaking free and leaving behind an empty space,” he says. “I liked that the paintings were 3-D.” To achieve that effect, Condo designed two simple canvas dresses for Chastain, taping them to the canvas and painting over them so that when they were removed, they would leave a blank space but appear to be a fragment of the piece. Standing in front of Condo's Abstract Conversations, 2012, with her red hair teased to eternity, Chastain blended into the cacophony of line and color, a member of the loopy crew. As Condo studied Chastain posing next to the other figures in the work, he began drawing a cluster of noisy characters close to her head to give the impression “that they were yelling into her ear.” While Chastain was having white makeup applied to half her face, Condo grabbed a scrap of paper and created an eye for her to use as a prop. “I thought if she just held it in front of her, it would give a real sort of Stanley Kubrick feel to the experience.” The result, of course, is suitably schizoid, just as Condo envisioned. “With that popped-out eye, there are two different sides to her face: one hysterical and the other soulful,” he says. “Multiple emotions at the same time.”


RINEKE DIJKSTRA There’s a breathtaking intensity to Rineke Dijkstra’s videos and large color portraits, perhaps owing to the way the Dutch artist and her subjects lock eyes and dare the viewer to look away. Dijkstra, whose midcareer survey earlier this year at the San Francisco Museum of Modern Art and at New York’s Guggenheim Museum won critical raves, focuses on people poised on the cusp of change: adolescents on the beach, mothers clutching newborns, bloodied bullfighters. Her subjects are aware of the camera but not practiced at manipulating whom it sees. Unlike them, of course, Jessica Chastain is well-versed in the art of presenting herself. Still, for Dijkstra, the process is always the same. Working with a 4x5 format camera, she places her subjects against a nondescript backdrop and waits for something to happen. “There has to be an interaction for the photograph to work,” Dijkstra says. “We have to be interested in each other.” Intrigued by Chastain’s porcelain-pale skin, Dijkstra wanted to shoot her wearing subdued colors that set off her red hair and blue eyes. But beyond the palette, the artist didn’t know what she was going to do until she and Chastain met in the studio. “I always work from observation and try to capture something from the clues I get,” notes Dijkstra, a master at conveying psychological nuance. “If you plan everything, there’s no room for interpretation. And Jessica was really open. She wasn’t hiding.”


CHANTAL JOFFE Chantal Joffe’s large-scale paintings celebrate the female form even as they distort it—to great effect—with thick, unfussy brushstrokes. Occasionally Joffe will paint her subjects directly from life or from photos she has taken of them, but more often, she borrows from fashion spreads, ads, and friends’ family snapshots. For her portraits of Chastain, Joffe tried something new: She simultaneously drew from photographs Max Vadukul had taken of Chastain in a bedroom at New York’s Gramercy Park Hotel, as well as from her own observations of Chastain, whom she directed in that shoot via Skype from her London studio. Joffe says the red-haired actress reminded her of nudes by Gustav Klimt, Egon Schiele, and Edvard Munch (“Her rawboned face seemed to me quite old-fashioned,” she notes), so the bed was covered with richly patterned fabrics. But when Joffe saw Chastain in person and in real time on her laptop, she says she glimpsed “a slight awkwardness to her that was sort of charming. I wanted to find a way to paint that—to know her slightly so I could hold onto the awkwardness and not make it too smoothed out or pretty-pretty. She had a way of slumping that was really natural. That felt like a blessing to me, because it’s hard for me to edit artifice out of my head.” Joffe first made watercolors to sort out details, then created enormous 10-foot works by using scaffolding. “As they go along, everything seems to become more exaggerated in the paintings. In one, she’s somewhat hunched and looks sort of startled and a bit annoyed; in the other one [above], she seems withheld—but in an empowered way, as if she’s in charge.”


MICKALENE THOMAS “What’s always intriguing to me is transforming my subjects into a character from another era,” says Mickalene Thomas, whose rhinestone-embellished collage paintings, photographs, and installations have regularly given African-American women a starring role. Posed as reclining odalisques, 1970s divas, and bold nudes, they express Thomas’s fascination with female power and stereotypes of black femininity. For this portfolio, Thomas photographed Chastain in one of the ’70s-inspired domestic interiors she had constructed for her recent retrospective at the Brooklyn Museum. She created “a performance inside a finished work of art” by instructing Chastain to “wait for your man to come home so you can seduce him.” Though Donna Summer blared from a record player and the set was reminiscent of the disco era, Thomas said her references ranged from portraits by Balthus and Edouard Manet to scenes from the 1983 film Scarface. She asked Chastain to channel her own version of the drug kingpin’s moll in that film (played by Michelle Pfeiffer) and had her blinged out from wig to toe in shimmering shades of gold. “I tend to gravitate toward characters who have a razor-sharp edge,” Thomas says. “I saw Jessica’s character as a woman who has conquered her environment. There’s a sense of triumph.” Throughout her career, the artist, who is African-American, has mostly painted “those closest to me—my friends and family,” but she insists that her choice of subject is not contingent on ethnicity. “I’m interested in their energy and the look in their eyes and the confidence they convey. It’s about the essence of their prowess.”