Ray Benson & Asleep at the Wheel Celebrate ‘Half A Hundred Years’

It seems like they have been around forever, yet at the same time it doesn’t seem like Asleep at the Wheel could possibly have banded together 50 years ago. The release of their Half A Hundred Years celebratory album, out October 1, is proof that the band has indeed been entertaining audiences with great music since 1970.

It all started when a 19-year-old Ray Benson, the band’s founder, wrote in his journal that he wanted to form a band to bring the roots of American pop music into the present. Benson had no idea that goal would take him and his group of dedicated musicians to stages around the world.

Benson, who was raised in Philadelphia, decided to drop out of college in 1969 to follow his dreams. He ended up in Paw Paw, West Virginia, where he and friends Lucky Oceans and LeRoy Preston became the roots of Asleep at the Wheel. The trio were known for playing real country music and took their sound to small bars in the Paw Paw area. Apparently their reputation spread beyond those humble beginnings, because to their surprise, in 1970 two hippie buses pulled up on the farm looking for this band they’d heard about. Inside were a group of musicians who went by the name the Medicine Ball Caravan. They liked what they heard from the Wheel and invited them to open a concert for them in Washington, D.C. It was Asleep at the Wheel’s first out-of-town show, but it wasn’t long before they were building a loyal fan base in the D.C. area.

“It was a pretty idealistic time,” Benson admits. “I was 19 and we ran around starving but happy, playing our music. We were playing these little bars in West Virginia, and they thought because we were hippies we wouldn’t fight. I stared down a few shotguns in my time, but I think it was the music that saved us because we were playing real country music.”

After their first visit to D.C., Asleep at the Wheel began playing rock-and-roll joints there. “We became known as hippies playing real country music,” Benson says. “We opened for Alice Cooper and Hot Tuna, and Emmylou (Harris) would come to see us. We played a double bill with Commander Cody and he encouraged us to give the Berkeley, California music scene a try.”

Never one to miss an adventure with their music, the group headed west, arriving in California in August of 1971. “We started booking clubs in the East Bay area and while doing a regular Tuesday night gig at one of the local clubs, Van Morrison came out to see us. He loved country music and asked us to do a show with him. During this period Rolling Stone magazine interviewed him and asked if he was excited about any new band he had heard. Morrison mentioned Asleep at the Wheel and the Los Angeles record companies came running.”

The group became the touring band for country singer Stony Edwards, one of the first black singers to have a presence in country music. They also joined him in the studio and played on his first release, “A Two-Dollar Toy,” for Capitol Records. Edwards loved the music of Bob Wills and working with Asleep at the Wheel was a great combination for him.

Asleep at the Wheel signed with United Artists and released its debut album, Comin’ Right At You and the first single off the album, and incidentally their first cover of a Bob Wills tune, “Take Me Back To Tulsa.” When released as a single, the song resulted in a good amount of airplay in Texas and Oklahoma. In February of 1973 the band moved to Austin, Texas, after being encouraged by Doug Sahm and Willie Nelson. Epic Records issued their second album the day they arrived in Austin, but it was a short-term association. They then signed with Capitol Records, and a song that would become one of their more popular tunes, “The Letter That Johnny Walker Read,” was released and became a top 10 country hit for them in 1975. In 1977 they were named the Top Touring Band by the Academy of Country Music and went on to win the first of 10 Grammys in 1979. 

When asked if there was ever a time when things got so rough he thought about quitting music, Benson admitted there were three or four times the challenges were great for the band. “After we had our big successes in the ’70s, then in 1981 disco hit and it was tough. We didn’t have record deal from 1981-1986, but we kept doing it because people kept saying how important the music we were playing was to them. I felt responsible for what we had started and that was when I knew what we were doing was more than a living – we were blessed with caretaking a form of music.”

In October of 1993, Liberty Records released Asleep at the Wheel’s 12th studio album and their first tribute album to Bob Wills, Asleep At The Wheel Tribute to the Music of Bob Wills & the Texas Playboys. Benson asked some of country music’s biggest artists to record with them, including Suzy Bogguss, Garth Brooks, Vince Gill, Merle Haggard, Huey Lewis, Willie Nelson, Dolly Parton, Leon Rausch, Riders in the Sky, Johnny Rodriquez and George Strait.

Their second tribute album to Wills in 1999, Ride With Bob, featured another round duets with artists including Clint Black, Mark Chesnutt, The Chicks, Lyle Lovett, The Manhattan Transfer, Tim McGraw, Reba McEntire, Lee Ann Womack and Dwight Yoakam. Their version of “Roly Poly” with The Chicks hit country radio in 2000, giving them the rare privilege of charting music across four consecutive decades.

The new album features several guest stars and includes new tunes along with some of Western swing standards. It also brought together some of the band’s former players (there have been 100 over the years) as guest players, including Chris O’ Connell, Leroy Preston, Lucky Oceans and Elizabeth McQueen. Among the guest stars are Emmylou Harris, George Strait, Lee Ann Womack, Johnny Gimble, Lyle Lovett and Willie Nelson.

The title track to the new album might not exist had it not been for singer/songwriter Jamey Johnson. Benson went to see Johnson at the Austin City Limits theatre and was telling him about it being the group’s 50-year anniversary. “He just looked at me and said, ‘That’s half a hundred years!’”

Great songwriter that he is, Benson immediately went home and started writing the song. “It came pretty quick; I think within a week I had it all down. I might have re-written a verse or two but it was pretty quick to write.”

The song is about the Wheel’s 50 years of music, sacrifices shared, the great experiences shared and places they’ve traveled to share their music with their amazing fans. Benson says he offered Johnson songwriter’s credit on the tune “but Jamey said ‘just mention my name’.”

The always popular “The Letter That Johnny Walker Read” features Lee Ann Womack, who Benson says is one of his favorite singers. He adds that he is not surprised that the song has held up so well over the years. “When me and Leroy wrote it we sent it to Porter and Dolly but they didn’t record it and I’m glad!”

Benson, Nelson and Strait do a great recording of “Take Me Back To Tulsa,” the song that got it all started for them. The recordings were done during the Covid-19 Pandemic, so most of them were done by each artist who sent their recording back to Benson. While Nelson did that, Strait came into the studio with Benson. “We opened a lot of George’s shows, and he just says he’s glad that we keep this music contemporary and around.”

Benson first met Nelson when he came out to see this band that played Bob Wills music. “He heard about us and came down to see us and over the years we’ve become great friends. We toured with him, Haggard and Ray Price and did an album with the three of them, Last of the Breed, released in 2007. (There is also a live-in concert video by the same name taped at one of their 2007 concert dates.)

While Benson says he has no idea what is ahead for the band in the next 50 years, he does know they will be busy through the end of the year. They kicked off the 50-year anniversary by playing Austin City Limit’s Music Festival in Austin October 1, and more dates in the West are followed by a return to Austin at the Moody Amphitheatre on October 15, where Benson promises a three-hour performance featuring very special guests and Asleep at the Wheel alumni.

Benson points to their live shows and great musicianship as reasons The Wheel has stayed around for 50 years. “I’m the reason we’re still together, but the reason it’s so popular is because we have had the greatest singers and players. That is all I have control over. When someone joins the band I say, ‘Learn everything that’s ever been done, then put your own stamp on it. I love to hear how they interpret what we do. I don’t know any other band that does the kind of music that we do.”