Route 66 at 100: How Artists Have Captured the Mythical Highway

Art World Route 66 at 100: How Artists Have Captured the Mythical Highway John Steinbeck immortalized it, Bob Dylan painted it, and Ed Ruscha photographed it. Here's how the Mother Road reshaped the artistic imagination. The Pacific Coast Highway may have the views and Route 50 the sheer span, but it’s Route 66, one of the U.S.’s first national highways, that has captured the imagination of writers, musicians, and artists across generations. On November 11, the iconic highway will be a century old. Made from a collection of pre-existing local roads, the trail began at Chicago, zigzagged through Missouri, Oklahoma, New Mexico, and Arizona, before reaching Santa Monica in California. Over the course of its life, Route 66 carried Dust Bowl migrants west, fueled America’s automobile tourism boom, and gave rise to the classic roadside motel. Route 66 was decommissioned in 1985 after years of decline, but segments of it remain preserved as National Scenic Byways. The legacy of the route has also been enshrined in the American cultural fabric: John Steinbeck called it the “Mother Road” in his seminal 1939 novel The Grapes of Wrath, Nat King Cole sang about rolling down the highway in “(Get Your Kicks on) Route 66” in 1946, and visual artists from Robert Indiana to Bob Dylan have mined it for inspiration. As the Route 66 Centennial celebrations kick off across the U.S., we take a short tour around some of the best-known artworks inspired by the Mother Road. Robert Indiana, Route 66 (1962) The self-professed “American painter of signs,” Robert Indiana had a long relationship with the road. “It seemed that half my life was spent in the automobile,” he said of his childhood in 1963. “We were always driving some place for something.” He also associated Route 66 with his father, who was born the sixth child in the family on the sixth day of the sixth month, and who worked for the energy company Phillips 66, named after a speed test at 66mph on Route 66 in 1927. When Indiana was 10, his father abandoned his family by driving down Route 66. The highway system first appeared in a couple of works in the 1960–61 series “The American Dream,” which commented on the “superficiality of American life” by nodded to such icons as pinball machines, neon signs, and highways 29, 37, 40, and 66. The legendary route was more overtly referenced in Route 66 (1962), in which Indiana captures the industry of America in large stenciled letters. The layout of the small painting—”USA” atop a monumental “66”—appears to take its cue from the Phillips 66 sign, which Indiana described as “one of the most fascinating visual objects in my entire youth.” Indiana never shook the subject. In 2002, he returned to Route 66 with US 66 (States) / US 66 (Cities), a diptych for which the artist revisited the signs he encountered while traveling down highways as a child. The paintings’ circular emblems name-check Texas, Missouri, Chicago, Flagstaff, and other stops along the route, while encircling a large number “6.” Ed Ruscha, Twentysix Gasoline Stations (1963) In 1956, Ed Ruscha journeyed down Route 66 from Oklahoma City to Los Angeles to attend the California Institute of the Arts, and the rising billboards and neon signs he saw would profoundly shape his work for the rest of his life. In 1962, he was back on the highway, traveling it in reverse from L.A. back to Oklahoma, and snapped 60 photographs of gasoline stations he encountered along the way. Twenty-six of these images were collected in his first artist book, simply titled Twentysix Gasoline Stations. Each image in the volume was plainly captioned with the station’s name and location. So, we get stops from “Union, Needles, California” to “Flying A, Kingman, Arizona” to “Knox Less, Oklahoma City, Oklahoma.” The minimalism of the book was entirely purposeful as Ruscha sought an “absolutely neutral” form with as little text as possible—a style that carries on through his later books. “My pictures are not that interesting, nor the subject matter,” he said in 1965. “They are simply a collection of ‘facts.’ My book is more like a collection of readymades.” Bob Dylan, “The Beaten Path” (ongoing) The one highway Bob Dylan has immortalized in song is Route 61 (the so-called “Blues Highway“), but his love for Route 66 is all over his visual art practice. For his ongoing series of works known as “The Beaten Path,” he has painted open roads, back roads, and country roads that wind across America. Most interesting for our purposes are his quiet, observational scenes along Route 66, including the historic Blue Swallow Motel, Grandview Motel, an abandoned garage, and a defunct Gulf station. “The common theme of these works having something to do with the American landscape—how you see it while crisscrossing the land and seeing it for what it’s worth,” Dylan wrote of the works when they went on view in 2016. “I believe that the key to the future is in the remnants of the past.” So, what’s Route 66 to do with Dylan’s past? Not much, unless you buy into his self-made lore that he spent his childhood in the railroad town of Gallup in New Mexico, which sits along the Mother Road. Highway 61, by contrast, originates in the artist’s very real home state of Minnesota. Then again, Dylan has always been more interested in mythology than geography. Ant Farm, Cadillac Ranch (1974) In 1974, a group of artists half-buried 10 Cadillacs just west of Amarillo, angling the automobiles on a 60-degree angle that mirrors that of the Pyramid of Giza. Titled Cadillac Ranch, the monumental installation by Chip Lord, Hudson Marquez, and Doug Michels—collectively known as Ant Farm—was designed to map the evolution of the Cadillac’s tailfin across the buried models, which span between 1948 and 1958. (Texas businessman Stanley Marsh 3, who commissioned the work, sourced and bought up the used Cadillacs via the classifieds in a local paper.) In a way, it’s a tribute to the golden age of the American automobile, one that likely zoomed down Route 66 in its heyday. The roadside attraction sat in a wheat field along Route 66 for decades until it was moved two miles to the west in 1997. Today, it is an iconic landmark that attracts more than a million visitors a year, many of whom have left paint and graffiti on the cars’ surfaces. The property is currently overseen by Stanley Marsh 4, who is looking into preserving the work. Lord, though, sees it another way. “With farmers, when a truck stops running, they put it out in a field and it rusts away. Just let it rust down to nothing, which eventually it will,” he said in 2024. “That’s the most logical end of Cadillac Ranch.”