Phases and Stages: A History of Country Crossovers

By Jason Jones / December 16, 2017

Traditionally country is the music of rebels and sweethearts born in the South and westward bound who’ve suffered a damn good story to tell. It is the music of loving and longing, mastery and insecurity, wonder and outrage, of hometowns and highways. It’s about hitching trains and picking up hitchhikers, about speaking the truth and singing the blues. It’s farm-fresh harmonica and the twang of pedal steel, it’s turquoise and tobacco, it’s barrooms and church ladies, and it’s cuttin’ out just like it’s cuttin’ in. Yes, country music’s as sensitive as it is sturdy, and as vulgar as vulnerable; it’s high, low, sexual and wise. “Three chords and the truth—that’s what a country song is,” Willie Nelson said. And whether you’re running from the law or missing your mama, it makes no difference, when the truth hits you there is no mistaking that country sound.

Country music is the establishment & the outlaws, it’s a cowboy in a long black Cadillac, a tough mama in a tight spot, and the images are indelible it seems, from Jimmie Rodgers to Jason Aldean, from Mother Maybelle to Shania Twain, but being as it is, at the crossroads of colliding forces, country has picked up its fair share of wayward hitchhikers and carried them down that crooked road—and some of them got to calling it home.

It’s these hitchhikers to whom this series pays homage: the artists who had not typically trafficked in country music…until they did. There is a long history, one that traces back to the earliest days of popular music, of artists who usually worked outside of Nashville, often established in other genres, moonlighting, coming from places like California, Canada, and England, who made legitimate country albums, some of which have since become embedded in the fabric of the establishment itself. Some of the names and albums I will cover in this series will not surprise most of you: Ray Charles’ Modern Sounds in Country and Western Music, The Byrds’ Sweetheart of the Rodeo, and Ween’s 12 Golden Country Greats are well known forays into country. But did you know a Monkee made a seminal leap into country rock? Or that Leon Russell took up a pseudonym and crowned himself a honky-tonk hero? Or that The Byrds were less than well-received by the Nashville elite when they arrived on the scene? I will introduce these stories and more, plus historical commentary and a look inside each of the albums featured, in a comprehensive chronology covering many of the most remarkable and unforeseen plunges into country music.

To begin with I will discuss three of the earliest detours into country, those taken by Bing Crosby, Ray Charles, and Bobby Darin.

Bing Crosby

Cowboy Songs (1939); Under Western Skies (1942); Don’t Fence Me In (1946, featuring the Andrews Sisters); Cowboy Songs Vol. I (1947); Cowboy Songs Vol. II (1948); Bing Crosby Sings the Great Country Hits (1963)

 Bing Crosby first experimented with country music in the early 1930s, just a few short years after country music’s cornerstone artists—the Carter Family, Jimmie Rodgers, Charlie Poole, and Gene Autry—made their first recordings, and not even a decade after the first Grand Ole Opry broadcast, the show which went on to help establish country as a mainstream genre. Crosby also beat many foundational artists to the punch. He released his first country recordings ahead of Roy Acuff, Eddy Arnold, Lefty Frizzell, Bill Monroe, the Stanley Brothers, Ernest Tubb, Kitty Wells, and Hank Williams. Not only did Crosby serve as an early bridge from mainstream pop culture to country, he remained in touch with country music throughout his life, releasing a number of new recordings and compilations over the course of a historically prolific career that saw him sell more than a billion records.  

Bing Crosby strutted into country in 1933 with the release of several covers, one of them being “Home on the Range,” which won him great success, however, it was the release of Cowboy Songs in 1939 that cemented his crossover into country. During the Great Depression and in the time leading up to U.S. involvement in World War II, a period in which President Roosevelt authorized New Deal legislation and construction of the first atomic bomb, he also named Bing Crosby’s “Twilight on the Trail” one of his favorite songs. While I like FDR’s taste in music in this case, I prefer Crosby’s version of the Johnny Mercer song “I’m an Old Cowhand (from the Rio Grande).”  It was recorded in 1936 with the Jimmy Dorsey Orchestra and released on 1939’s Cowboy Songs. It exemplifies many of the tendencies we will see in later crossover artists. There’s subtle humor, an emphasis on songwriting and arrangement, and a commingling of phrases joyous and blue. Have a listen.

Perry Como, Frank Sinatra and Dean Martin are counted among the singers influenced by Crosby’s famous bass-baritone voice and magnetic style, and it would not surprise me if country greats such as Hank Williams and Johnny Cash knew a Bing Crosby track or two. After all, his celebrity and influence was widespread during his lifetime. He won an Academy Award for Best Actor for his portrayal of Father Chuck O’Malley in Going My Way (1944), has his star on the Hollywood Walk of Fame, and was a star of film, television, radio, and the stage. He was truly a multimedia sensation and he remains a pop culture icon. It is less known, but a substantial part of his legacy nonetheless, that Crosby released a number of country albums during his career, often scoring big hits with the singles. On his final country release, 1963’s Bing Crosby Sings the Great Country Hits, it’s clear that Crosby must have truly enjoyed country music (or maybe he was just talented enough to capitalize on it), as he pushed himself beyond the cowboy and swing styles from his earlier recordings, and embraced the tunes of Nashville’s next generation of great songwriters, including Bill Anderson, Jenny Lou Carson, Hank Cochrane, Don Gibson, Harlan Howard, and Willie Nelson. Glen Campbell was also a member of the recording band.

Here’s Crosby’s cover of Willie Nelson’s “Hello Walls.”

So, here’s to a white Christmas and an updated legacy for Bing Crosby—he’s more than just that Christmas guy—he’s one of the most versatile artists in the history of show business, and one of the first to crossover into country music. It just so happens that his final country release occurred just after Ray Charles released Modern Sounds in Country and Western Music, the critically-acclaimed breakthrough that pioneered the modern era of switching lanes into country music.

Ray Charles

            Modern Sounds in Country and Western Music (1962)

Ray Charles’ career in music began in the late 1940s, but it was not until the 1950s that he began to score hits. “Mess Around,” “It Should Have Been Me,” and “Don’t You Know” were early successes for the soul star. Later in the decade he had hits with “I Got a Woman,” “This Little Girl of Mine,” “A Fool for You,” “What’d I Say,” and more. His first foray into country music came in 1959, when he released a cover of Hank Snow’s “I’m Movin’ On.” But a proper dance with country would have to wait, as 1960 was the year in which Charles became a breakout star with the release of “Georgia on my Mind.” He took home a total of four Grammys for the song and album. Coming on the heels of his great success, however, were hard times for the singer, as he was busted for heroin possession while on tour in 1961. The charges were ultimately dropped, but this was the first in a series of missteps that ultimately led to his falling out of popular favor, though not the dismantling of his majestic legacy.

In 1962 when Modern Sounds was recorded and released, not only was Ray Charles straddling a mighty river, with one foot on the side of magnanimous glory and one on the side of hollow desolation, but the nation, nay, the world was standing over the throes of incredible forces of division. As it turned out, 1962 also marked the turning of an era for America and American music.

A plethora of culture shaping events occurred in 1962, many of which marked the end of a more primitive way of life and the beginning of this modern, technological, consumption-driven existence. The U.S. landed its first spacecraft, Ranger-4, on the moon, putting America abreast of the Soviet Union in the space race; the first Wal-Mart opened; Nelson Mandela was arrested under apartheid policy; Johnny Carson assumed the desk at The Late Show; the first James Bond film, Dr. No, starring Sean Connery, premiered; Andy Warhol debuted his groundbreaking exhibition Campbell’s Soup Cans; the Civil Rights movement gained prominence; the Cuban Missile Crisis put the planet in the crosshairs of dissolution; and Marilyn Monroe died.

1962 was also a year of seismic importance in popular music. Or, as rock-prophet Col. Bruce Hampton put it during his interview with Jarrett Bellini, published to Youtube on January 5, 2016, “1962 was the worst year of music ever, right before the Beatles and all the 60s renaissance happened. And so when it gets that bad, something changes.”

So what was happening in music the year that Modern Sounds premiered?

The Beatles, under the tutelage of Brian Epstein, made their first recordings with George Martin in Abbey Road studios, bringing together the iconic Fab Four lineup for the first time; Bob Dylan released his eponymous debut and began the Freewheelin’ sessions; the Rolling Stones formed; and the Beach Boys scored their first hits. These landmark events, all precursors to the new and earth-shattering wave of change about to sweep through pop culture, do not, however, get at the heart of 1962. Psychedelics had not yet made a mark, the electric guitar was held in a different light, the folk revival was not yet prevalent; rock wasn’t even a thing yet, but rock n’ roll was still the thing in 1962, as it had been in the fifties…but not the only thing. True, alongside Ray Charles, Aretha Franklin, Herbie Hancock, Miles Davis and Nina Simone were offering the first glimpses at a new brand of music, however, the purveyors of the last generation of popular genres were still overwhelming the airwaves. Rock n’ roll stars past their hey-day, including Elvis Presley, Chuck Berry, Jerry Lee Lewis, and Bill Haley and his Comets remained at a commercial peak, while blues purveyors who began performing in the 30s and 40s, Howlin’ Wolf, Ella Fitzgerald and Dinah Washington for example, capitalized on the burgeoning blues revival. Yet style-setters of an even earlier generation, including Tony Bennet, Frank Sinatra, Johnny Mathis and Nat King Cole, also persisted in scoring hits at the top of the charts. So 1962 was truly a year of change and upheaval, but it mostly happened under the radar, thus making for one of those awkward listening phases, but setting the stage for Modern Sounds in Country and Western Music, an uncommon breakthrough in a strange time.

Meanwhile in 1962, over on the country side of the recording industry, Charles shared the airwaves with many of the stars of country’s golden age, including Bill Anderson, Chet Atkins, Johnny Cash, Patsy Cline, Ferlin Husky, George Jones, Loretta Lynn, Buck Owens, Webb Pierce, Jim Reeves, Marty Robbins, Faron Young, and more. Modern Sounds and the single “I Can’t Stop Loving You,” a Don Gibson cover, made a splash on the country charts and both were certified gold.

Listening to Modern Sounds, one comes to appreciate the anatomy of the songs, the arrangements, the timbre, the attitude: the very breath and pulse by which Ray delivers these classic ballads hangs by a thread and binds you to his soul. So much care is taken in these recordings that there are galaxies to discover just by carefully listening; it’s like auditing a dangerous workshop taught by “The Genius” himself. Keeping in mind the goings-on in the world at the time, one can point to a further awareness and deeper understanding on the part of Brother Ray, who made such a bold, barrier-crossing cultural statement, which was simultaneously a timeless triumph of artistic interpretation.

Much credit is deserved for the arrangements on the part of Gil Fuller, Gerald Wilson, and Marty Paisch, which added to the precision of instrumentation perfectly illuminating the lyrical emotion in the songs. The fleeting vocals, the interplay of instruments, the exuberance, and restraint, matched with these pristine country ballads makes for some of the most profound outpourings from the legendary musician. The perfectly designed moments created in these ballads is breathtaking. The Genius brings so many rootsy influences to bear on the polished gems on Modern Sounds, arriving like a tornado and plundering country’s tower of song, testing the integrity of the structure as its dwellers could never imagine nor dare, but only to learn and further prove that the tower was built to last. Here’s a heart-wrenching rendition of the Hank Williams standard “You Win Again,” in which Charles breathes new life into the timeless tune.

Not only does Ray Charles deftly handle one of the cleanest songs Hank Williams ever wrote, scaling the genre’s highest mountain so to speak, but he is able to transcend the limits imposed on what most people would consider traditional country music. Because of his knack for brilliant gestures, and in view of his racial identity and cultural awareness, as only a true artist is capable of, Ray Charles is sometimes able to elevate a country standard to a new level of meaning and resonance. When he sings Eddy Arnold’s “Just a Little Lovin’ (Will Go a Long Ways)” he infuses the song’s overstated sentiments with a dose of soulful irony that redefines the song’s cultural value, while aptly calling attention to the overriding racial inequalities that played into the song’s tone-deaf portrayal of reality. Charles singing “why don’t you put your arms around me / and I’ll be your slave” gives context and import to the original that makes Arnold’s version ring out hollow at best. In Ray’s possession, with his virile, sensual voice in all its glory, the song represents the flowering of American culture indeed, bringing to bloom so many seeds planted in the dark.

Ray Charles lived his life like a country song, like a country singer. As a child he witnessed his brother drown and started losing his sight soon thereafter. He was born in Georgia, moved to Florida, then out west to Seattle. He died in California and Willie Nelson sang at his funeral. He climbed to the top of the charts and bottomed out, rose again and lives now in immortality. Like Bing Crosby before him, he is connected to the Academy Award for Best Actor, as Jamie Foxx took home the honor in 2004 for his portrayal of the Father of Soul in Ray. To some extent, however, Ray’s legacy has become dependent on this film, though his songbook and influence deserves more contemporary attention. Also like Crosby, Charles continued playing country music deep into his career.

Here’s a video from 1984 of Ray Charles and Willie Nelson performing the Troy Seals and Eddie Setser tune “Seven Spanish Angels.”

Bobby Darin

            You’re the Reason I’m Living (1963) 

Bobby Darin is an original rock n’ roll darling, a Grammy winner, a Rock and Roll and Songwriters Hall of Famer, and a prominent social activist—so much so that he was present when Bobby Kennedy was assassinated. He has his star on the Hollywood Walk of Fame and even won a Golden Globe for his role as Tony in 1961’s Come September, which co-starred Rock Hudson and Sandra Dee, Darin’s first wife. His first big break came in 1958, when he recorded “Splish Splash.” His next releases included hits such as “Dream Lover,” “Mack the Knife,” and “Beyond the Sea,” giving him international exposure.

The worst year in music ever is the gift that keeps giving, as 1962 just so happens to be the year Darin made his first country recordings, though You’re the Reason I’m Living did not appear until 1963. The timing and innovation of his first country exploration puts Darin in the discussion of being one of the true, early forerunners in the country rock revolution of the late 1960s, bridging the gap between the early days of original rock n’ roll and country. Ray Charles changed the game by putting Nashville’s best songs through R n’ B and cultural boot camp, completely transforming them in the process, but Darin’s contribution foreshadowed the union of country and rock that would go on to speak for much of the twentieth century. While many of his contemporaries were busy riding out the rock n’ roll wave, he was on the trail of the next big thing. Here he is interpreting the Hank Williams / Jimmie Davis song “(I Heard That) Lonesome Whistle.”

This track (and others) makes it sound as if the orchestration of Ray Charles’ Modern Sounds was a substantial influence on Darin’s crossover, however, it’s his traditional rock n’ roll leanings that provide an early context for country rock. A less emphatic use of horns, except for one notable section, on the rollicking cover of Don Gibson’s “Oh Lonesome Me” is a taste of a country rock sound that did not come to prevalence for another decade, yet it simultaneously hearkens back to the western swing era.

The title track, a Darin original, showcases his crystalline voice in a country register, while also highlighting his songwriting talents. The style alludes to Hank Williams, but the harmonica is a portent of country rock, and the layered, cinematic orchestration and bare vocals are remarkably familiar in the country revival of the 1990s. Compare Whiskeytown’s “Paper Moon” with “You’re the Reason I’m Living” and there are noticeable similarities.

Like Bing Crosby, Darin enjoyed international fame and a multimedia career that included starring roles in music, film, radio, and television and helped to give country a wider mainstream audience; and like Ray Charles, just as rock n’ roll was running out of breath, Darin realized the blossoming of genius occurring in Nashville—critically dubbed the golden era of country—and tapped it to make inspired and inspiring music. You’re the Reason I’m Living is a shining example of a country crossover album and an affirmation of his place in music history, but Darin had another major impact on country rock: he helped to discover and then mentored Roger McGuinn, who went on to found The Byrds. Their album Sweetheart of the Rodeo has long since become the gold-standard of country crossovers.

Join me next time for a fresh look back at The Byrds’ Sweetheart of the Rodeo, Judy Collins’ Who Knows Where the Time Goes, and Bob Dylan’s Nashville Skyline. 

About the author

Jason Jones

Jason Jones lives in St. Louis, Missouri. He holds an MFA in creative writing from Florida International University. Previous and forthcoming poems can be found in Cumberland River Review, The Ilanot Review, J Journal, Saw Palm, Wraparound South, and others.