It’s a bit like Wonderland, walking into a contemporary art museum these days. You’ll be encountered with a surprising hotbed of activity: a variety of blips and beeps, neon lights, looped videos and sensation-blurring installations. Fall down the rabbit hole, and you’ll rethink the very definition of art.

The pioneers of this expanding artistic frontier came of age during Post-WWII America. The last half of the century saw a swell of patriotic optimism following the war, as communities became more affluent, progress was gained from Civil Rights and the Women’s Movement, and technology ushered us into the Space Age—the artistic community naturally grew within these contexts. In a vast departure from realism, artists explored new media and subject matters, reaching meteoric success and commanding unheard of sums at auctions. See how these 20th-century trailblazers lit up the world and changed the way we can experience art.

Elaine de Kooning (1918–1989, Brooklyn, NY)
Elaine De Kooning, Les Eyzies (1985). Portrait by Timothy Greenfield-Sanders.

Demonstrating an interest in art from an early age, Elaine’s most important instructor, the Dutch artist Willem de Kooning, would later become her husband in 1943. It was rare for a woman to be part of the machismo Abstract Expressionist group (think Jackson Pollock), but she was accepted into the Eighth Street Club and was central to the artistic social circles of the bohemian heydays in the West Village. While also painting, she supported herself as an associate editor at Art News magazine, advancing her husband’s career while also becoming recognized as a critic. Her most significant commission was painting JFK during the final year of his presidency—she was chosen because her work reflected the Expressionist genre of the time, but also because she worked quickly. She once said, “A painting to me is primarily a verb, not a noun,” an essence which is captured through the swift brushstrokes in her work. While being shadowed by her famous husband, her work has received posthumous critical acclaim, and can be seen at MoMA, the Met and the Guggenheim, and she received a retrospective at D.C.’s National Portrait Gallery in 2015.

Robert Rauschenberg (1925–2008, Port Arthur, TX)
Robert Rauschenberg, Studies For Chinese Summerhall II (1984). Portrait courtesy of The Nationaal Archief, The Netherlands.

Robert Rauschenberg anticipated the Pop Art movement. His six-decade career embraced popular culture through painting, sculpture, silkscreens, choreographic collaborations with Merce Cunningham and Paul Taylor, a stint with NASA during its launch of Apollo 11 in 1969, a cover about the Vietnam War for Life magazine and the album art for Talking Heads’ Speaking in Tongues for which he earned a Grammy. After studying at art schools, he moved to NYC and became part of the Neo-Dadaist movement, resonating with the philosophy of Marcel Duchamp. He created work alongside Jasper Johns and Cy Twombly, traveling to Europe and creating collages out of trash. He’s most recognized for his “combines” which were collages that were part painting, part sculpture, turning found objects into something new, using newsprint, painting, taxidermy, pieces of clothing and debris. Anti-elitist and always investigating “the new,” Rauschenberg’s work welcomed in the world. Coming from a working-class family in rural Texas, he became a global art star by the end of his career, and even inspired a play by Charles Mee called bobrauschenbergamerica.

Garry Winogrand (1928–1984, Bronx, NY)
Garry Winogrand, Muhammad Ali, Oscar Bonvena Press Conference, New York City, 1970 (1983). Portrait by Judy Teller, courtesy of Greenwich Entertainment.

With a gravelly Bronx accent and a mug that beckons a film starring Benicio del Toro, Garry Winogrand was a standout in his generation of street photographers in the 1960s and ’70s. Growing up in a working-class family of Jewish immigrants, Winogrand lived in a time where photography wasn’t a career-maker—at best in the “Mad Men” era, a person could earn a living through photo-journalism or advertising. Winogrand studied painting at City College and Columbia University, but he quickly latched onto photography and lived his life through a lens thereafter, taking more than a million photos (many of which were developed posthumously). His quick, almost haphazard style of taking a photo, and his gifted eye for spotting choreographed scenes, produced raw, candid shots of real life and turned Winogrand into a sensation, pushing the notion that photography could reach the heights of the other fine arts.

James McGarrell (1930, Indianapolis, IN)
James McGarrell, Basso Continuo (1984). Portrait by Jonathan Williams.

For years, people have been enthralled by James McGarrell’s symbolist oil paintings. The eye certainly must travel in his vibrantly colored landscapes and interiors, giving off a kaleidoscopic effect of energy and texture. By observing his studied, layered technique, splashed with improvisational geometries, it’s no surprise to learn that jazz is one of his influences. Having earned a BFA, MFA and a Fulbright, McGarrell knows the rules well enough to break them, delivering sui generis works from the depths of his imagination. His mysterious narratives often use 20th-century artists as his subject matter, such as Billie Holiday and Charlie Chaplin, and have garnered more than 100 worldwide solo exhibitions. His work is part of the permanent collections at MoMA, the Hirshhorn and Centre Pompidou, among others, and it has been presented at five Whitney Annuals and Biennials.

Bruce Nauman (1941, Fort Wayne, IN)
Bruce Nauman, Human Nature (1983). Portrait courtesy of Phaidon.

Bruce Nauman is one of the world’s most compelling artists, who exploded the idea of what art can be. During his decades-long career, he has explored conceptual work in the genres of videography, performance, sound, sculpture and neon…his work must be experienced. Moving to San Francisco in the ’60s, Nauman started a studio with a tabula rasa approach, unsure of just what would be produced that day, but with the goal that every day must be spent making art. Believing that art doesn’t have to be “pleasant,” his installations are filled with absurdity and violence. An example of his creative genius is the Raw Materials exhibit at the Tate Modern in London (2004), which was a string of disembodied human voices and ambient tones that the attendees could walk through, listening to words like “OK, OK, OK” on loop, which were delivered in a variety of intonations and rhythms before morphing into something else. Nauman’s work isn’t complete without his audience, and he leaves us to interpret his creations as we see fit, appealing to our emotions as well as our intellect.

Robert Cumming (1943, Worcester, MA)
Robert Cumming, Apex Oculus (1986). Portrait courtesy of the Video Data Bank.

Robert Cumming’s career rose during the 1970s, becoming a renowned painter, sculptor, printmaker and photographer, having obtained his BFA at Massachusetts College of Art and MFA at the University of Illinois, Champaign. While in Los Angeles, he became obsessed with old photographs of Hollywood sets, which showed the mechanics of how scenes were artificially brought to life. While filmmakers focused on manipulating reality to create the perfect image, Cumming worked to expose those illusions. He built functionless sculptures meant for his black & white shots, using humor and absurdity as a commentary on how we receive and misperceive sensorial information, pushing the boundaries of narrative in photography. His work has been exhibited at the Whitney, MoMA and the Hirshhorn, and his most recent exhibit, The Difficulties of Nonsense (2018), is currently on tour across the country. Influenced by Duchamp and Rauschenberg, his work invites the viewer to take a closer look.

Jeff Koons (1965, York, PA)
Jeff Koons, Luxury And Degradation (1986). Portrait by Sebastian Kim/August Image, LLC.

Alchemists of yore would be stunned by Koons’ power to transform cheap inflatable balloons into gleaming metallic monoliths. Taking the art world by storm, his silver Rabbit sold for nearly $91.1 million this year at Christie’s, the most expensive artwork to date by a living artist. His colorful, playful themes are often humorous with a darker nod to mortality (those inflatables deflate, after all). At the cross-currents between Pop Art and Surrealism, Koons has explored the boundaries between art and marketing, hoisting pristine household items onto gallery walls, turning the objects we ignore into subjects worthy of contemplation. His process is a technologically complex amalgamation involving science, CT scanning and old-school techniques like lost wax casting—while his artworks may look simple, their creation and installation are never easy.

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