Bob Dylan’s 2025 Outlaw Music Festival Covers: Route 66
The song: “(Get Your Kicks on) Route 66” Played May 13, 2025, in Phoenix, Arizona, the first stop of the 2025 Outlaw Musical Festival Tour.
The Hotel Monte Vista, 100 North San Francisco Street, Flagstaff, Arizona, just off Route 66 — Bob Dylan, Beaten Path series,
The Genesis of a Classic: Bobby Troup and “(Get Your Kicks on) Route 66”
The story of one of America’s most enduring road anthems begins with a journey, both literal and aspirational. The creative mind behind “(Get Your Kicks on) Route 66” was Robert (Bobby) Troup Jr., an American jazz pianist, singer, songwriter, and actor, perhaps best remembered by those of a certain age for his role as Dr. Joe Early in the 1970s television program Emergency!.
The moment of inspiration struck in 1946. Troup, accompanied by his then-wife Cynthia, embarked on a cross-country drive from their home in Pennsylvania to California. They traveled in their 1941 Buick with the dream of Troup establishing himself as a Hollywood songwriter. Their journey initially took them along U.S. 40, and Troup considered penning a tune about that highway. However, it was Cynthia who suggested the title, “Route 66,” as they transitioned onto the western highway.
The song began to take shape during their ten-day trek westward. Troup later recounted that the melody and the titular phrase, “Get your kicks on Route 66,” came to him with relative ease. The remainder of the lyrics, however, proved more challenging. It was only after arriving in Los Angeles and consulting a map that he filled out the song, creating a lyrical travelogue by listing the cities and towns that dotted the highway’s path.
A painting of the Gateway Arch, Saint Louis, Missouri and the skyline, Mississippi River view. Bob Dylan, Beaten Path series, 2023
The lyrics serve as a mini-travelogue, celebrating the romance and freedom of the open road by tracing the westward trajectory of U.S. Route 66 from Chicago, Illinois, to Los Angeles, California. The song name-checks a series of locales, inviting listeners to “get hip to this timely tip” and make the journey: St. Louis and Joplin in Missouri; Oklahoma City, Oklahoma; Amarillo, Texas; Gallup, New Mexico; Flagstaff, Winona, and Kingman in Arizona; and Barstow and San Bernardino in California, before reaching the golden promise of the Pacific coast.
The song found its initial popular success through Nat King Cole. The King Cole Trio recorded “(Get Your Kicks on) Route 66” on March 15 or 16, 1946, with its official release on April 22 of the same year. It swiftly became one of Cole’s signature early hits, achieving remarkable chart success by reaching number three on Billboard magazine’s Race Records chart and number eleven on its broader pop singles chart in 1946. This triumph was a pivotal moment in Cole’s career, elevating him from a respected jazz pianist to a bona fide pop superstar.
The song’s impact was immediate and far-reaching. The phrase “get your kicks on Route 66” quickly permeated the American vernacular, becoming a shorthand for adventure, excitement, and the quintessential cross-country road trip experience. The song’s release was perfectly timed, coinciding with the post-World War II era, a period characterized by a surge in automobile ownership, an optimistic national mood, and a burgeoning desire for leisure and exploration. Troup’s composition, therefore, didn’t just describe a highway; it tapped into and amplified a defining cultural moment.
“Route 66”: Charting a Course Across 1960s America
The iconic television series “Route 66” captivated audiences from 1960 to 1964 with its tales of two young men, Tod Stiles and Buz Murdock (and later Lincoln Case), traversing the highways of America in a Chevrolet Corvette, seeking adventure, work, and a deeper understanding of themselves and their country. The CBS drama, which aired for 116 episodes, was notable for its on-location filming, a rarity for its time, which provided a rich and authentic backdrop to its stories.
Painting of White Bus ‘El Trovatore’ belonging to the Trovatore Motel, Kingman USA. Home of the ‘longest map in the world’ [of Route 66] Bob Dylan, Beaten Path series
Diverse Interpretations Across Genres
The robust melodic structure and evocative lyrical journey of “(Get Your Kicks on) Route 66” proved to be fertile ground for musical reinterpretation. Since its debut, the song has transcended its jazz origins to become a true standard, covered by a vast array of artists across numerous genres, each version reflecting different musical sensibilities and eras.
Shortly after Nat King Cole’s hit, Bing Crosby, accompanied by The Andrews Sisters, recorded their version in 1946. It climbed to number 14 on the Billboard chart, demonstrating the song’s immediate and widespread appeal beyond Cole’s initial audience.
As music evolved, so did “Route 66.” Rock and roll pioneer Chuck Berry included a driving, energetic version on his 1961 album New Juke Box Hits. Berry’s take infused the song with a new rhythmic vitality and became a significant influence on subsequent rock interpretations. This influence was clearly heard when The Rolling Stones featured the song on their 1964 self-titled debut album. Having learned it from Berry’s recording, their rendition became one of their most popular early in-concert numbers and is often cited as “the most famous rock version” of the tune, introducing it to a global audience during the British Invasion.
Betty Boop Route 66. Another view of the El Trovadore Gas Station behind the motel of the same name. Bob Dylan, Beaten Path series
U.S. Route 66: The Mother Road of America
Parallel to the song’s journey through musical history is the story of the highway itself — U.S. Route 66, a ribbon of asphalt that carved its way into the American psyche.
U.S. Route 66 was officially commissioned on November 11, 1926, as part of the nation’s first Federal highway system, launched by the Bureau of Public Roads. Oklahoma highway official Cyrus Avery played a significant role in its initial mapping and in securing the “66” designation. Rather than being an entirely new construction, its path was a pragmatic cobbling together of existing local, state, and national roads.
The original intent behind Route 66 was to connect myriad rural towns to each other and to major urban centers like Chicago and Los Angeles. This approach was envisioned to benefit farmers, manufacturing companies, and local merchants by providing improved access to markets and attracting new revenue to often isolated communities. The U.S. 66 Highway Association actively promoted the route, famously advertising it as “the shortest, best and most scenic route from Chicago through St. Louis to Los Angeles”.
A painting of the Glancy Motel, 217 West Gary Boulevard, Clinton, Oklahoma. Bob Dylan, Beaten Path series
Stretching approximately 2,448 miles, U.S. Route 66 embarked on an epic journey across the American landscape. The highway traversed eight states: beginning in Illinois, it wound its way through Missouri, made a brief passage through the southeastern corner of Kansas, then cut across Oklahoma and the Texas Panhandle. Its final stretches crossed New Mexico and Arizona before culminating in California. The official starting point was Chicago, Illinois, and its western terminus was Los Angeles, California, with Santa Monica later becoming recognized as the iconic end-point.
During the Dust Bowl of the 1930s, Route 66 became the primary artery for the westward migration of hundreds of thousands of displaced farm workers and their families, often referred to as “Okies,” fleeing ecological devastation and economic hardship in search of a new life in California. It was John Steinbeck’s seminal 1939 novel, The Grapes of Wrath, that immortalized this desperate exodus and famously dubbed Route 66 “The Mother Road, the road of flight,” cementing its place in the national consciousness as a path of both suffering and hope.
During World War II during the 1940s, the highway assumed a critical strategic role. It was used extensively by the War Department to transport troops, vital equipment, and supplies across the country. Furthermore, Route 66 facilitated one of the largest wartime mobilizations of labor, as thousands of jobseekers headed to defense plants on the West Coast, contributing to the war effort.
The post-war boom of the late 1940s and 1950s saw Route 66 transform again. With increased automobile ownership following the war and the lifting of wartime travel restrictions, traffic along the highway surged dramatically. It became a vibrant symbol of newfound American freedom, economic optimism, and the quintessential family vacation. The catchy phrase from Bobby Troup’s song, “getting your kicks on Route 66,” became inextricably linked with this burgeoning tourism experience, beckoning a generation to explore the nation’s diverse landscapes.
Wigwam Motel Holbrook AZ. Bob Dylan, Beaten Path series
Icons of the Roadside
The increased traffic along Route 66 spurred the growth of a unique roadside culture. “Mom-and-Pop” businesses — motels, diners, gas stations, and an array of quirky roadside attractions — sprang up to cater to the needs and curiosities of travelers. This entrepreneurial spirit gave rise to many iconic landmarks, some of which still stand today as testaments to that era: the whimsical Blue Whale of Catoosa, Oklahoma; the interactive public art installation of Cadillac Ranch in Amarillo, Texas; the World’s Largest Covered Wagon in Lincoln, Illinois; the distinctive architecture of the Tower Station (U-Drop Inn Café) in Shamrock, Texas; the historic Ariston Café in Litchfield, Illinois; and the Threatt Filling Station near Luther, Oklahoma, notable for being one of the few Black-owned businesses that served African American travelers during the era of segregation. This vibrant and often eccentric roadside culture became a defining characteristic of the Route 66 experience and a visual symbol of American ingenuity, local entrepreneurship, and folk art.
Ranch Kitchen Steak House Gallup New Mexico Bob Dylan, Beaten Path series
The Interstate Shift: The Beginning of the End
The passage of the Federal Aid Highway Act of 1956, strongly championed by President Dwight D. Eisenhower who had been impressed by the strategic efficiency of the German Autobahn during World War II, authorized the construction of the Interstate Highway System. These new superhighways were designed for high-speed, limited-access travel, and their routes often bypassed the small towns and Main Streets that were the lifeblood of Route 66. Over the subsequent decades, sections of Route 66 were gradually superseded, bypassed, or directly incorporated into these new interstates. For instance, Interstate 40 now roughly parallels much of Route 66’s former path through states like Texas and Arizona.
After years of being incrementally replaced, U.S. Highway 66 was officially decommissioned as a federal highway in 1985. This act marked the formal end of its nearly 60-year service as one of America’s principal transcontinental routes.
Both grassroots movements and official bodies began working to protect and promote the legacy of the Mother Road. Associations were formed to encourage travel along its remaining segments and to advocate for its preservation. States started designating sections as “Historic Route 66” and erecting distinctive signage to guide nostalgic travelers. Federal recognition followed with the passage of the Route 66 Study Act of 1990 (Public Law 102–400), which acknowledged the highway’s symbolic value as part of “the American people’s heritage of travel and their legacy of seeking a better life”. This legislation led to studies by the National Park Service and the eventual establishment of initiatives like the Route 66 Corridor Preservation Program, aimed at protecting and interpreting the road’s significant resources.
Today, many segments of the original Route 66 are still drivable, often maintained as state or national scenic byways. Decades after the highway’s peak and its formal removal from the federal highway system, and nearly eighty years since the song’s debut, both “Route 66s” — the musical anthem and the legendary roadway — maintain a potent hold on the collective imagination.
Both the song and the road evoke core American values and myths: the allure of freedom, the spirit of individualism, the narrative of westward expansion, the promise of reinvention, and the timeless appeal of the journey itself. “Route 66,” in both its forms, is not merely a historical artifact; it is a living, breathing part of an ongoing American story, a journey that continues to unfold.
Played live by Dylan before? Nope.
Other Dylan connections?
The Nat King Cole version “(Get Your Kicks on) Route 66” was played by Mr. D. on the “Street Map” episode of Theme Time Radio Hour way back in 2008. While his The Philosophy of Modern Song has chapters on 66 songs, none mention Route 66.
In one of his earliest radio appearances, on Oscar Brand’s “Folksong Festival” on WNYC in October 1961, a 20-year-old Bob Dylan made a notable claim about his origins. When Brand mentioned Dylan was born in Duluth, Minnesota, and asked if he was raised there, Dylan responded, “I was raised in Gallup, New Mexico,” a town situated directly on Route 66. Pressed further by Brand about the kinds of songs he encountered in Gallup, Dylan elaborated, “You get a lot of cowboy songs there. Indian songs. That vaudeville kind of stuff.” Dylan’s assertion was part of a broader collection of tall tales Dylan spun during this period, which included claims of being a hobo, an orphan, a descendant of the Sioux Nation, and having traveled with carnivals.
Associating himself with Gallup, New Mexico, and by extension Route 66, allowed Dylan to tap into the romanticized imagery of the American West — its ruggedness, its perceived authenticity, and its storied past. This resonated with the folk movement’s valuation of “roots” and hard-won experience, adding a layer of mystique to his burgeoning identity. The Gallup claim, though debunked by Newsweek magazine, persisted as part of his early legend.
On the art front, there are several artworks by Dylan that explicitly reference Route 66 or its distinctive landmarks, including those featured in this article. Dylan’s visual art demonstrates an explicit engagement with Route 66. “The Beaten Path” series, and particularly its dedicated “Route 66” collection, features numerous works depicting specific landmarks and evoking the atmosphere of the historic road. The pieces underscore a sustained and direct artistic interaction with the highway, suggesting it is a compelling subject for Dylan’s visual interpretation.
