A Lifetime of Being Asleep at the Wheel

Despite his Texas bona fides, Western swing superstar Ray Benson hails from a Jewish background in Wyndmoor.

At 6 feet, 7 inches tall, Ray Benson casts a large shadow even when he isn’t sporting a 10-gallon hat, spangled Western suit and cowboy boots. In mid-November, when he calls me from his recording studio in Austin, Texas, the baritone-voiced front man of the nine-time Grammy Award-winning Western swing band Asleep at the Wheel assures me he is dressed much more casually. In fact, he says, he is wearing the Merion Golf Club golf shirt he received about five years ago when he played in a tournament at the Ardmore club.

It seems fitting he is sporting a bit of Philly: The 64-year-old grew up in Wyndmoor, around the corner from where my own family lived. Known then as Ray Seifert, he was a childhood friend of my brother, Alan. So even though Benson officially moved away from the Philadelphia area in the 1970s — eventually landing in Austin at the urging of his good friend and golf buddy Willie Nelson — he is at heart a Philadelphian and a proud product of its Jewish community.

Although he was named Texan of the Year in 2011 and Texas State Musician in 2004, his considerable musical accomplishments have only just been acknowledged here in his hometown. A musician, singer, bandleader and songwriter, he’s been onstage with the likes of Bob Dylan, Dolly Parton, Charlie Rich and Emmylou Harris, and performed for Presidents George W. Bush, Bill Clinton and Barack Obama. Yet it was not until last month that he was named to the Philadelphia Music Walk of Fame, along with The Trammps (“Disco Inferno”), Jerry Blavat and The Roots. Benson, who was in town for the ceremony that gave him a bronze plaque on the sidewalk near the Kimmel Center, says it was “so cool” to be in such company. He recalls the reception he got from the audience at the event. “All of a sudden this big cowboy gets up and says, ‘I bet y’all are wondering how a Jewish kid from Philadelphia became a cowboy-singer. I can tell you in two words: Sally Starr.’ They all just died laughing.”

Benson’s answer elicited laughter, but he was serious. While other baby boomers his age likely watched Sally Starr’s Popeye Theater television show and delighted in the antics of Roy Rogers, Dale Evans and Fess Parker’s Davy Crockett on their shows, most quickly grew out of their cowboy fascination. Benson grew into his.

Perhaps it all began when he was 7 and his family took him to see Gene Autry when the star was making a personal appearance at WCAU on City Line Avenue. It was a moment Benson has never forgotten. Benson is in a reminiscing mood, trading stories with me about our shared idyllic upbringing in Springfield Township, Montgomery County, where he spent a lot of time outdoors in the woods catching toads, snakes and frogs and riding horses. The nostalgic look back has been prompted by his new, anecdote-filled memoir, Comin’ Right at Ya: How a Jewish Yankee Hippie Went Country, or, the Often Outrageous History of Asleep at the Wheel (University of Texas Press, 2015).

When the publisher first contacted him, Benson quickly agreed to work with writer David Menconi because he thought it was time — after 25 Asleep at the Wheel albums and four decades of live performances — to share his life story. He explains, “For 45 years, I have existed as this guy who everybody thinks was born on a ranch in Texas and is probably Baptist.” When he would point out that he was Jewish, the once skinny, red-haired Benson was often told he neither looked nor sounded Jewish.

Benson also agreed to the book because he had taken more than 70,000 words worth of notes throughout his career that were just waiting for a professional writer to turn into a book. Among the improbable anecdotes he tells in Comin’ Right At Ya is the story of how he coaxed Janis Joplin’s rental car into starting when Big Brother & the Holding Company was playing in Philadelphia, and how he bummed cigarettes from the Grateful Dead’s Jerry Garcia — both of which happened when he was a teen. He even showed up at Woodstock, although he and his friends left before they heard any music.

Benson’s own career as a performer began at age 10, when he and his sister Sandy performed with a folk music group called The Four G’s. Benson, who played guitar, found himself hooked on performing when the children’s group played with the Philadelphia Orchestra in front of 5,000 people.

While he excelled at music, mastering the sousaphone and bass and playing in orchestras and marching band, Benson had a tough time in school; although highly intelligent, his attention deficit disorder made it hard for him to concentrate, and he frequently got in trouble for talking in class.

After graduating from Penn Charter in 1969, Benson enrolled in Antioch College in Yellow Springs, Ohio, as a filmmaking student, but dropped out in 1970 to start Asleep at the Wheel with friends Reuben Gosfield and LeRoy Preston. The idea was to bring everything they loved about Western swing music, which developed in the 1920s in the Southwest, to a new generation of fans who would appreciate its combination of jazz and blues accented by trombone, trumpet, clarinet, guitar and steel guitar. Benson describes it as “a great amalgamation of Afro-American, jazz, blues, swing and Texas country fiddling.”

Some 100 musicians have played with Asleep at the Wheel over the years and today Benson remains its only original member. His son, Sam, 32, has produced the group’s last two albums and plays guitar on them. Son Aaron, 29, edits movie trailers in Los Angeles.

Like his friend Willie Nelson, who just turned 80, Benson has no plans to retire. He neither feels his age nor acts it, and still spends quite a bit of time on the road, traveling in his tour bus to appearances. Every 18 months or so, he and his band will do two shows at the Sellersville Theater.

He says, “The only time I’ll stop is when it stops me. If I can’t do it or people stop coming or my fingers don’t work, or my voice don’t work.”

Gail Snyder recently put Asleep at the Wheel into her Spotify.