‘Half A Hundred Years’: Ray Benson Weighs in on the Last 50 Years of Legendary Roots Group Asleep at the Wheel

When Ray Benson told Jamey Johnson that his band, Asleep at the Wheel, was coming up on their 50th anniversary, Johnson responded, ‘That’s half a hundred years!’” This humored perspective got Benson thinking about the sacrifices made for the sake of this era-defining outfit. As he sat down with this new song title, highlights of his experiences—the places they’ve been and the people they met and played for—flooded into what would become the title track of Asleep at the Wheel’s milestone album, Half A Hundred Years.

Out on October 1 via Thirty Tigers and Home Records, the 19-track collection reunites the original band members and welcomes back friends and career-long collaborators, including Willie Nelson, George Strait, Lee Ann Womack, Lyle Lovett, and more. The guest list is just a sample of the rotating cast of musicians who contributed to Asleep at the Wheel’s ever-expanding legacy over the years and speaks to the defining nature of the band and their imprint on American music traditions. 

 It’s a story, Benson says, about how “a tall skinny Jewish kid from Philly” became a fervent purveyor of age-old music traditions and steady leader of an enduring American roots band over the course of five generations since their unlikely inception in 1970.

“Well, you’ve got to understand, it’s 1969, and hippies and rednecks did not mix,” Benson tells American Songwriter. At the time, Benson was enrolled at Antioch College in Ohio, Leroy Preston was studying in Boston, and Lucky Oceans was a college student in Columbia, Maryland. Oceans reached out to Benson and Preston about a friend whose father owned an orchard outside of Paw Paw, West Virginia, and had a log cabin that he deemed “perfect” to finally start their band.

“When people asked where we were moving, and I said West Virginia, they looked on a map and said, ‘You’re gonna get killed,’ Benson laughs. “The Peter Fonda film, Easy Rider had just been released and there was this great scene where they kill Dennis Hopper. But off we went into uncharted territory, and we fell in love with the place.”

Upon arrival, the recent Manson murders deemed the bounding trio of hippie teenagers as suspects in the small community. They moved to the next county over where they met some hippies working on a hog farm that invited them aboard their medicine ball caravan on the way to DC to play a few concerts. Benson’s brother joined them for harmonies, and they picked up a bass player along the way to Washington where they managed to open a show for Alice Cooper and Hot Tuna.

“It was pretty naïve and cool, which was what you would hope out of 19-year-olds,” says Benson.

Back and forth they went between their metro following in DC—where EmmyLou Harris would come to see them play—and their local honky-tonk gigs for the “hillbillies and rednecks” around Paw Paw. The contrast felt especially stark as the band adamantly opposed the Vietnam War. As a native of the Northeast with an educated background and left-leaning politics, Benson learned to navigate the disparaging division with poise. 

“My reaction was we need to take this music to my generation to show them it’s not the political posturing that is important, it is the soul of the music,” says Benson. “It was the same thing, except that it’s hard because nowadays, if you say anything on stage, about the current situation, the pandemic, the reaction, Trump, etc., you’ve got a political divide in the audience,” he says. “The one thing that works out is that music keeps it together. People come together, who have totally disparate opinions and enjoy the music together. So that’s the first step. If we can just get them to enjoy the music together, maybe they will realize that the beliefs that they hold are their own. And maybe there are no absolutes here.”

Asleep at the Wheel became a cornerstone of the Austin, Texas, scene upon its arrival in 1973. Steeped in the regional influence of Western swing and honky-tonk country, their soundscape expanded. By 1978, the face of the original band changed as most of the players decided it was time to hang up their hats. Facing a crossroads as he watched them exit, Benson committed to the group he started nearly a decade before and went looking for the right people to step into the roles.

“All I always kept doing was finding people who wanted to play music with me,” says Benson. “That was it; it’s pretty simple. You go find the people who have the ability to do what you want to do and convince them that they ought to come join you to do it.”

For 50 years, Benson has served as a constant figure in the face of an ever-rotating cast of talented musicians. The artist credits himself for Asleep at the Wheel being around all these years later. But as to why the group has garnered and sustained popularity, Benson says, “it’s because we’ve had the greatest singers and players.”

To ensure the continuity of the age-old music traditions, Benson was responsible for finding competent musicians that not only could play what was on the page but players who were also dexterous enough to jam along and work hard for little pay.

Understanding the roots and anatomy of the band allowed him to recruit the most fitting talent. He drove a hard bargain but was able to sell himself to prospective players for next-to-nothing because of his strong musical convictions. “Some people do that with financial incentives, but we had no money, so it was all musical incentives,” he continues. “I said ‘You want to play a kind of music that is really cool that nobody else is doing and nobody’s buying, and you’ll probably go broke?’ ‘Oh sure, let’s go do that.’”

Not to say there hasn’t been what many would define as financial and musical success over the years, but Benson resolves it’s been few and far between. The driving force, for five decades, has been an insatiable desire to deliver the music of America to a captivated live audience. “That’s the thing, it’s the freedom to do what you want to do musically, regardless of the consequences,” he says. “That’s what this band has always been about.”

Each of the countless players the band has hosted over the years instilled a dynamic element or influence to contribute to Asleep at the Wheel’s ever-evolving sound. “It was Americana before there was this ‘Americana Chart’ thing,” says Benson. “To play this American music on the road, in a different town every night, you need players who improvise. What people have to understand is there’s nothing written down; we’re not reading music and each solo that is played is improvised. So that is a tradition of American music that certainly worth preserving.”

Listen to Half A Hundred Years, here.