Ray Benson

Swing Ambassador: 50 Years of Asleep at the Wheel
Ray Benson
Ray Benson: Brooke Hamilton.

“Why are you all playin’ that modern music?”
Asleep at the Wheel guitarist Ray Benson fielded the question from Harry, a regular at the Sportsmen’s Club in rural Paw Paw, West Virginia, after singer Chris O’Connell fronted their jazzy rendition of the Bob Wills favorite “Right or Wrong” as part of the band’s earthy retro-country repertoire that charmed locals wary of hippies, but to Harry, the ’20s pop tune sounded weird with its jazzy melody and changes.
“To him, it wasn’t hillbilly music,” Benson laughs.

“I had pretty lofty goals as an 18-year-old. I did say we were going to change country music. Our generation rejected country because of the political side – Vietnam, hippies, rednecks, whatever. Our thing was, ‘How could you reject Merle Haggard’s music just because of ‘Okie from Muskogee’ and ‘Fightin’ Side of Me,’ which maybe we didn’t believe in at that time? It was the roots of country music. That’s what we were concerned about – it was slippin’ away. We wanted to do our own version – play this music, but make it our own.”

Benson and childhood friend Reuben Gosfield, a.k.a. Lucky Oceans, both left college at age 19 to form the band in 1970. Joined by mutual friend Gene “Leroy” Preston, they settled in a cabin near Paw Paw to hone their talents.

Half a century later, Benson, co-founder, leader, vocalist and songwriter, reflects on five decades of triumph, setbacks, honors, and endless personnel (and gear) changes that helped revive Western swing. The road to eight Grammys (and 27 nominations) began in a comfortable suburban household just outside Philadelphia.

Benson’s ’51 Epiphone Zephyr, ’48 Triumph, and late-’40s/early-’50s Deluxe Regent.

Ray Benson Siefert, born in 1951, was one of four children. His parents and siblings were all music-oriented. After playing recorder and taking piano lessons, at nine he discovered his sister’s tenor guitar; a year later, he joined her and two other kids in a folk quartet called the Four Gs (each played a Goya nylon-string) – “The standard for suburban folksingers,” he laughs.

At one Four Gs performance, Benson remembers, “This guy had an f-hole archtop. I’m thinking ‘Wow! What’s that?’ He was comping chords as opposed to ringing chords. I was intrigued.”

As the Four Gs scattered in 1965, Benson dug deeper into music with Lucky, whose parents were kind of suburban beatniks.

“They knew jazz and collected 78-rpm records,” Benson said. “Their collection spanned jazz, blues, and folk.

Benson’s guitar bevy includes these Buck Owens and Merle Haggard tribute Telecasters.

“The journey was to hear people you like, and play their stuff – rock and roll, jazz – I learned how to play ‘Misty.’ I could read music because I was studying bass and tuba. A lot of worlds opened up.”

A neighbor taught him to play Lonnie Mack’s “Memphis” and his jazz interest grew through older brother Mike, a musician wired into the robust local scene.

Benson still owns his first steel-string, a Regal resonator he calls “not a great guitar.” As rock exploded at home and overseas, the 16-year-old worked as a lifeguard in the summer of ’67 to afford gear, starting with a Harmony 335 he played through his dad’s tape recorder.

“I plugged it in and pressed ‘Record.’ That was my first amp. It had a 4″ speaker!”

A Fender Bandmaster soon filled the void before he bought a Telecaster Custom for $125.

“That’s where I learned to play electric guitar. It had flatwound strings and I couldn’t bend anything; nobody told me wound strings are a lot easier to bend.”

Lucky’s love of blues enabled them to explore B.B., Albert, and Freddie King, Muddy Waters, and R&B. Ray also gravitated to the jazz virtuosity of Barney Kessel and Herb Ellis. They were both part of short-lived units like the Red Eye Blues Band, followed by Orange Juice – “a bad psychedelic rock band.”

Benson took paying gigs on bass and began writing. He’d often join Lucky to haunt the pawn shops on Philly’s South Street, adding, “I bought some incredible guitars I wish I’d kept.”

The friends absorbed Buck Owens, Ernest Tubb, Johnny Cash, George Jones, Hank Thompson, and Merle Haggard; Lucky’s 78s introduced both to Wills.

As graduation approached, he bought a Guild Thunderbird.

His Collings SoCo 16 LC Deluxe is now the only semi-hollow he takes on the road.

“Muddy played one and Zal Yanovsky played one in the Lovin’ Spoonful, and mine was great but I pawned it in Oakland when I moved there in ’71.”

While studying filmmaking at Antioch College, he heard Commander Cody and his Lost Planet Airmen, with Bill Kirchen on Telecaster. Their madcap, twanging mix of country, Western swing, and rockabilly inspired his original concept.

Recruiting Lucky (who attended an Antioch campus in Maryland) and Preston, they settled in an unheated cabin near Paw Paw in March, 1970. Lucky, playing lap steel, coined the name Asleep at the Wheel. As musicians came and went, the Sportsmen’s Club remained a training ground.

“Four sets a night, you get to play everything – Ernest Tubb’s ‘Thanks A Lot’ and ‘Let’s Say Goodbye Like We Said Hello.’ Leroy and I sang Hank Williams and Merle Haggard. Our big numbers were Roy Acuff’s ‘Wreck on the Highway,’ Hank Williams’ ‘Settin’ the Woods on Fire’ and anything by Buck Owens, like ‘Cryin’ Time.’ We wrote songs in that form.”

“I turned to Lucky and said, ‘Man, I’m tired of just playin’ turnarounds. Let’s do some more Bob Wills stuff, where we can play all solos.’ For that, you had to practice, and we practiced every day.” They also landed a few gigs in Washington, D.C.

Late 1970 brought singers Chris O’Connell and Emily Paxton to Paw Paw, both from D.C. Emily soon returned home but O’Connell, able to handle swing, blues, and Loretta-Lynn-style country, remained.

“We took it seriously. We started out pretty raw and through hard work and playin’ all the time, got pretty good in a year and a half.”

Haggard’s 1970 album, A Tribute to the Best Damn Fiddle Player in the World (or, My Salute to Bob Wills), deepened their understanding of his music.

“It was a game changer,” Benson said. “Because of quality of the recording, we could actually hear the bass and other stuff we were missing on the 78s.”

Ray and Lucky also delved into the complex country-jazz instrumentals of Ernest Tubb’s band, Texas Troubadours. Starting with “Redskin Rag,” the pair emulated the incandescent team of guitarist Leon Rhodes and pedal-steel man Buddy Charleton.

Still in contact with the Berkeley-based Commander Cody, Asleep moved west in August, 1971. Settling in Oakland, they played local bars, briefly toured with country singer Stoney Edwards, and opened shows for Van Morrison. After he lauded Asleep in a 1972 Rolling Stone interview, major labels took notice and they signed with United Artists.

Benson onstage in ’77, testing the load limit of a blackface Pro Reverb.

Benson used some of the advance money to purchase a modified 1960/’61 Gibson ES-355 for $500. The seller claimed it was owned by Leon Rhodes, who favored Epiphone Sheratons (not Gibsons), but when Ray showed it to Rhodes, “Leon told me, ‘The frets are filed flat. I’d never do that.’”

Benson played it into the ’80s before selling it to the Hard Rock Café.

Comin’ Right at Ya, a 1973 country/swing effort produced in Nashville by ex-Bob Wills/Buddy Holly guitarist Tommy Allsup, earned praise, but poor sales led United to drop them.

The band met Doug Sahm and Willie Nelson in California, and both lauded Austin’s fast-growing music scene, adding that Asleep would fit in. After playing one gig in a year, they relocated and began touring nationally. A 1974 album mixing country, swing and vintage R&B also fizzled.

Writing an appreciation of Wills for Country Music Magazine, Nelson name-dropped Asleep, noting they “…do the old Bob Wills songs exactly.”

“We listened to the guys the Playboys were listenin’ to,” Benson says. “Who was (guitarist/arranger) Eldon Shamblin listening to? Charlie Christian. (Pianist) Al Stricklin was listenin’ to Fatha Hines. We went back to the source.”

A formidable, versatile singer, O’Connell also became a capable rhythm guitarist. “She was a solid chunker,” Benson says admiringly. “She had a bunch of guitars including a wonderful Gibson L-50.”

1975 brought a new label, Capitol – and success. Texas Gold was a seamless mélange that refined their blend of authoritative, confident Western swing, country, and R&B. The album and the barroom-weeper first single “The Letter that Johnny Walker Read” reached the country Top 10. A year later, they were showcased on the debut episode of Austin City Limits.

Benson got to know other Austin talents, the Vaughan brothers among them. “Stevie and I were just friends and we’d jam. Watching the progress of a musician going from good to great is amazing; Stevie was going from good to great to legendary. “

Meeting and working with former Texas Playboys bestowed even greater education. “I stole from Eldon, absolutely. Just watchin’ him, sittin’ next to him, that was quite an experience. He was amazing. We did sessions with him, (fiddler/electric mandolinists) Tiny Moore, and Johnny Gimble. Eldon would say, ‘You play this, you play this, you play this and you play that.’ That’s what he did on the Wills band.”

Did Willie’s Django-inspired picking influence Benson?

“Absolutely! And of course, his phrasing, which is the same as his vocal phrasing – behind the beat, ahead of the beat, over the beat, whatever. I learned so much from Willie. He’s not a technical player. And Willie don’t read nothin’ – he’s a total by-ear player, but so sophisticated and so original. “

Despite four albums, Grammy nominations, and a 1979 win for their roaring big-band Western swing version of Count Basie’s “One O’Clock Jump,” Capitol dropped them.

“The ’80s were very rough – from ’80 to ’86/’87,” he recalls. “We didn’t have a record deal. Willie would let me go to his studio and record, so we had a record, but nobody wanted it.”

1982 saw Lucky marry and move to Australia; O’Connell departed four years later. New members came and went.

“About ’82, I had to bill the band as Ray Benson and Asleep at the Wheel because people were wondering, ‘Who’s gonna show up?’ I said, ‘As long as I show up, they’ll accept that this is Asleep at the Wheel.’”

Their 1987 album, 10, launched a turnaround by reaching the country Top 20 and yielding a Top 20 single with the ’40s tune “House of Blue Lights.” Two instrumentals – “String of Pars” and Hank Garland’s “Sugarfoot Rag” – earned Grammys.

After selling his 355 to Hard Rock, Benson used an ES-347 he calls “a great guitar” and an ES Artist with its active electronics disabled. Visiting the Samick booth at an early-’90s NAMM show, a solid guitar body hanging on a wall caught his eye. The company had just bought Valley Arts.

“I said man, that is gorgeous! What is it?” He had them complete the instrument and for years it served as his primary. They later built more for him and in 2005 he traded one to the Hard Rock to reacquire his beloved 355.

Asleep’s resurgence brought a series of Wills tribute albums beginning with Tribute to the Music of Bob Wills and the Texas Playboys, joined by contributors ranging from Dolly Parton and Chet Atkins to Haggard and Huey Lewis. One instrumental, “Red Wing,” earned Grammy number four. The album spawned two follow-ups – Ride with Bob, which also became a stage presentation, and Still the King.

An institution by the early ’00s, they performed at the White House for President George W. Bush and for 2008 Presidential candidate Barack Obama, who joined them onstage to sing a bit of “Boogie Back to Texas.” A year later, they teamed with Nelson for Willie and the Wheel, an album-length excursion into Western swing favorites by Wills and others.

Benson has an Epiphone Zephyr Regent and matching amp he’s used on records since 1975.

“I use a reissue Fender Deluxe on the road. I leave my ’67 version at home. I also have this 1938 National amp; instead of grillecloth, it has a Dobro cover.” And, there’s a 1970 Fender Princeton; “I still use it but not on the road.”

He also leaves his archtops at home except for the Collings SoCo 16 LC Deluxe. “I’m big, and I need a bigger guitar to get a little lower-end sound,” he said. I just love it. Collings is one of the top two guitar manufacturers in America – they’re perfectionists.”

String choices are consistent, and mostly wound – .012, .014, .017, .036, .040, and .052. – though he has an old ES-5 with flatwounds.

His favorite players are diverse. For lead he says, “Jimmy Wyble is who I wanted to be… (and) T-Bone Walker.”

Freddie Green and Shamblin remain his rhythm heroes. “I’m a chunker, man (laughs). I’m an okay lead player, but I’m a real good rhythm player. I love the Nashville rhythm players, but I was introduced to Freddie when I was 15, and playing bass. And Eldon is the best.”

He’s also a fan of amazing players outside the genre.

“Tommy Emmanuel is just amazing, and there are so many out there in the jazz world – John Abercrombie, Bill Frisell, Wes and Django and Barney Kessel, Johnny Smith and Herb Ellis.”

Behind the scenes, Benson’s son, Sam Siefert, produces the records and manages the band as head of Bismeaux Productions.

While Benson was stricken with Covid-19 in 2020 as the pandemic curtailed tours and delayed recording projects, in early ’21 he toted his J-200 on small-venue tours as the Asleep at the Wheel String Band with the band’s two fiddlers and bassist.

“We got tired of sittin’ on our asses, and I figured, ‘Let’s go do what we can.’ We’ve all been vaccinated. We’re fine.”

Size notwithstanding, reflecting on the hundreds of musicians who’ve passed through over the past half-century, he concludes, “Anyone who plays the Wheel’s 100 to 150 shows a year gets better. It’s a muscle, man, you gotta use it!”

Asleep A-Listers

Past members reflect on their time in the band

Lucky Oceans

Lucky Oceans: lap and pedal steel 1970-1982

“It’s been a great ride with Ray, and getting to be a long one, too!” says Reuben Gosfield, a.k.a. Asleep at the Wheel steel guitarist Lucky Oceans, who gave the band its name. They “met” as children living in the Philly suburb of Wyndmoor.

With music-loving parents and their eclectic collection of 78s, Oceans delved into various styles, and the Byrds’ 1968 Sweetheart of the Rodeo album especially impressed him. Buying 78s introduced him to Bob Wills, and Leroy Preston further expanded his (and Ray’s) interest in country and vintage R&B.

His first live exposure to the instrument was lap-steel blues man Freddie Roulette with Charlie Musselwhite in a Philly club, and steel players on records became heroes, including various Texas Playboys along with Don Helms, Jerry Byrd, and L.A. Western-swing icon Earl “Joaquin” Murphey.

Oceans arrived in Paw Paw with a borrowed six-string lap steel tuned in E. He later traveled to Manny’s, in Manhattan, to buy a Sho-Bud pedal steel he tuned in E9. Sho-Bud co-founder Shot Jackson’s sons later gave him a doubleneck Professional model he still owns; Buddy Emmons became his pedal hero. He also acquired a Rickenbacker lap steel, tuned in C6.

The band’s name came to him by “mixing a trucker’s theme – ‘Don’t fall asleep at the wheel’ – with the idea humanity is hurtling forward with lots of momentum but not much thought-out direction.”

California and Austin were his turning points.

“With the addition of [bassist] Tony Garnier and pianist Floyd Domino in the Bay Area, and the assistance [in Austin] of Johnny Gimble and Tommy Allsup, the band was able to build on those rough-and-ready West Virginia beginnings.”

Texas Gold, he adds, was a bellwether that “solidified our eclectic approach and belief there was a unity of roots music,” especially between the hard-to-pigeonhole genres of Western swing and R&B. So far as his own great moments on record, he cites his C6 lap solo on “Take Me Back to Tulsa” from Comin’ and “Dead Man” from Asleep’s second album.

Oceans married and moved to Australia in 1982, where he remains, performing roots music with the bands Dude Ranch and Zydecats, while also hosting presentations and world music programs for Australian media. Distance, however, hasn’t eroded his ties to Asleep; he won a second Grammy for his work on their 1993 Bob Wills tribute album and appeared on their 25th Anniversary “Austin City Limits” reunion. A reunion album of the original band is in the offing.

“It was great fun and a privilege to learn as we grew up, and experience all those crazy times together. We were a team, but it was always Ray who had the vision and the dedication of how to keep the wheels rolling. And how amazing that it’s still going today, and we’re all still around!”

Chris O’ Connell

Chris O’ Connell: vocals, rhythm guitar 1970-’86

“Look,” Ray Benson counseled the unsure young woman who arrived unannounced at the band’s Paw Paw headquarters in the fall of 1970. “You either want to do this or you don’t. If you do, you need to get busy and learn songs.”

“A rhythm player was born,” Chris O’Connell warmly remembered.

She and her friend/singing partner, Emily Paxton, had seen Asleep open for California country-rockers Poco in Washington, D.C., on October 4, 1970. “We came out knowing the Wheel was infinitely cooler, way more captivating, and musically hipper.”

An Arlington native, her parents were jazz-minded; her father played alto sax in the ’20s and ’30s, her mother loved Ella Fitzgerald, Sinatra, the Mills Brothers, and Keely Smith.

O’Connell used Leroy Preston’s D-35 and Takamine acoustics until she bought a Gibson L-50 (nicknamed “Chester”) “…for a couple hundred bucks in Berkeley. I played it standing in front of a mic for years. I didn’t have to hear it. I could feel it, and came to love the driving power.

“I didn’t start deliberately listening to rhythm players until after I started in the band,” she admits, crediting Comin’ Right at Ya producer Tommy Allsup, himself a rhythm specialist, with guiding her through the 1972 sessions.

Ronnie Earl showed her chord progressions and patterns backstage at a Roomful of Blues show. “I’ll be forever grateful, not only for him sharing some cool stuff with me, but for embracing me as a fellow musician and not just ‘the girl.’”

Working with Johnny Gimble and other Texas Playboys was especially fulfilling. During the 1975 Texas Gold sessions, she says, “Gimble put a tenor banjo in my hands one minute before the tape rolled on ‘Fat Boy Rag,’ and said, ‘It’s only three chords! You can do it!’ And I did!”

“When I saw Freddie Green at an impromptu jam in New York City with a scaled-back version of the Basie band, I stood mere feet from him and watched his hands. I was transfixed.” Her Green-style comping is heard on the Grammy-winning “One O’Clock Jump.”

Now living in the Bay Area, she performed pre-pandemic with her band, The Smart Alecks, which includes former Asleep steel-guitarist Bobby Black. Her trusty ES-295 was stolen last summer, but she still uses her L-50.

“Only Ray has the secret to keeping the style going, with the revolving door of talent,” she reflects. “The Wheel is his baby, and his job is to protect it, nurture it, enable it to grow. I slept, played cards, drank, and chunked on my L-50. I never had to make a business call or arrangements to pull the bus out of a ditch.

“Asleep gave me a platform, and for the most part, free rein to sing whatever I wanted,” she said. “They gave me a space to feel authentic. It was music school, and I loved that part of it. As they say in Ft. Worth, ‘I wouldn’t trade.’”

Cindy Cashdollar

Cindy Cashdollar: steel 1992-2001

“I’ll give you six months,” Ray Benson told Cindy Cashdollar when he hired her to replace John Ely as Asleep at the Wheel’s steel guitarist. In nearly a decade of recording and touring, she earned five Grammys for her work on two of the band’s Bob Wills tribute albums.

Cashdollar took up steel very late in life and played around her native Woodstock with Levon Helm and Rick Danko before spending five years playing dobro with Leon Redbone. In Austin, she studied steel with Ely, Maurice Anderson (creator of MSA steel guitars) and former Texas Playboy Herb Remington. “Great teachers, all three of them,” she recalls warmly.

“Ray keeps the flame of Western swing, and in a way, he’s like Bob Wills. He’s bringing stuff to the public, but I think he’s in sync with what the public wants. He was the embodiment of Western swing – carried on where it left off and knew all about the horn-section sound, the fiddle, and the steel.”

Benson and other band members enlightened her as to the steel’s vital role.

“I had to think like a horn, and how a horn would attack, soften, or punch the note. The parts were set in stone. A lot of those arrangements would change. I didn’t read or write music. Still don’t.

“When I joined, I had a doubleneck, and realized I had to learn more tunings, so I got a triple-neck.”

She used a three-neck Fender Stringmaster, often with a Peavey amp through Asleep’s endorsement deal. Her tunings were E13, C6, and A6.

“Keeping one neck in reserve, I could try one riff out each night in a strange tuning until I got comfortable with it.”

Her horizons widened when she met former Texas Playboys Remington, guitarist Eldon Shamblin, and fiddler/mandolinist Johnny Gimble. All occasionally recorded and performed with Asleep.

“That was an eye-opener to watch Eldon and Herbie and Johnny in the studio – one take, usually. I remember Eldon came in one day, set up, walked over, and plugged his guitar in. I turned to him and said ‘What settings are you using?’ He said ‘Oh, hell, I didn’t even look!’”

Cashdollar departed amicably in 2001 and before covid, worked with them occasionally.
“I am so grateful to have had the opportunity to work for somebody such as Ray, who has such conviction. That band is his life. To work with such incredible instrumentalists with such history really was the opportunity of a lifetime.

“I was so happy for the opportunity to be in a band with an instrument slated for country music, getting to play jazz and swing, blues, covers, and everything under the sun that Ray had the good sense to do. I’ll always be eternally grateful to him for giving me a chance.”

This article originally appeared in VG’s August 2021 issue. All copyrights are by the author and Vintage Guitar magazine. Unauthorized replication or use is strictly prohibited.

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