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How Ricky Skaggs Redefined Bluegrass and Brought It to the Mainstream

Neotraditional star infused his Eighties hits with exceptional playing and Appalachian harmony

“Sounds just like the old days!”

That’s how Ricky Skaggs greeted fans and friends gathered for a one-off show in Nashville on Saturday, September 2nd. The “old days” to which he was alluding were part of the point of the show, staged at the Nashville Palace and touted as his first country performance in 20 years.

With a red Fender Telecaster slung around his shoulders for much of the night and in command of a full band, Skaggs delivered a barrage of best-known hits and deep cuts: “Heart Broke,” “You May See Me Walkin’,” “Honey (Open That Door),” “I Don’t Care,” and “Only Daddy That’ll Walk the Line,” which he recorded as a duet with Waylon Jennings, among others. The playing, as one would expect, was exceptional, and his mountain tenor sounded just as pure as it did 30 years ago.

His low-key, conversational presence also ensured that the emphasis was squarely on his song selection as well as superior musicianship from all corners. It was both a joyful stroll down memory lane and a reaffirmation of Skaggs’ permanent place in the country and roots pantheon. Still capable of outplaying nearly anyone, Skaggs is also the artist who, at least for a brief spell, brought bluegrass straight into the mainstream.

Skaggs had his first country Number One, at age 27, in April 1982 with the weepy ballad “Crying My Heart Out Over You.” It kicked off an incredible run of 12 chart-topping hits, placing him in the first wave of country’s celebrated neotraditional movement along with George Strait, John Anderson and Randy Travis. He was invited to join the Grand Ole Opry in 1982 – the youngest performer to receive the honor at the time.

Originally recorded by Flatt & Scruggs in 1960, “Crying My Heart Out Over You” bore obvious traces of Skaggs’ musical past: Skaggs, a child prodigy on the mandolin, had once played “Foggy Mountain Special” with the iconic bluegrass duo on television when he was just 7 years old, and appeared on stage with Bill Monroe. As a teenager, he honed his instrumental chops and harmony singing as a member of Ralph Stanley’s Clinch Mountain Boys alongside fellow Kentucky native Keith Whitley, before going on to more progressive territory with J.D. Crowe and the New South, the Seldom Scene, Boone Creek (which featured Vince Gill and Jerry Douglas) and even Emmylou Harris’ Hot Band.

His mainstream country output in the Eighties reflected that pedigree, frequently packing dazzling bursts of instrumental wizardry into tight 3-minute songs or updating traditional forms with a more expansive, full-band sound. He’d taken a progressive stance with his vision of bluegrass – which, like the rest of country music, has its staunch purists – making the case that the amplified guitars of rock & roll and pop-literate songwriting could be presented through a bluegrass lens. Hits like “Heartbroke” and “Highway 40 Blues” were written by respected Nashville songwriters like Guy Clark and Larry Cordle, respectively, but Skaggs just as often selected material written by his bluegrass heroes like Carter Stanley and Bill Monroe, filling them with lonesome, multipart vocal harmonies straight out of the Appalachian Mountains. That ability to mix sources old and contemporary in a manner that didn’t seem stilted is evidence of Skaggs’ shrewd pop instincts, a keen understanding of his own journey and the flexibility of a good song. In 1985, at the height of his popularity, he was named CMA Entertainer of the Year.

Though he never left it completely behind, Skaggs returned fully to bluegrass with the 1997 album Bluegrass Rules!, stowing away the electric guitars and drums. Since then, he’s steadily churned out albums at roughly the pace of one per year, sometimes collaborating with fellow ace pickers or paying tribute to the work of his bluegrass forefathers. His later, more experimental explorations have included collaborations with jazz-influenced pianist and songwriter Bruce Hornsby, as well as Ashley Monroe and Jack White side project the Raconteurs on “Old Enough.” In 2015, he toured with Los Angeles-based guitarist Ry Cooder, another roots aficionado capable of playing in many different modes. He also served as producer on Lady Antebellum singer Hillary Scott’s family gospel project Love Remains. The instrumental prowess of bluegrass has a thread through all of these, but none of them hold fast to rules around tradition.

Many of Skaggs’ neotraditional contemporaries found other ways to address the changing landscape in country in the Nineties. George Strait recalibrated his sound slightly to remain one of the format’s biggest draws, John Anderson had a second life on the country charts with a more rock-tinged sound on “Money in the Bank” and “Seminole Wind,” and Randy Travis kept right on having hits through 2002’s “Three Wooden Crosses.” Both Strait and Travis are now in the Country Music Hall of Fame, while Skaggs is not, though you don’t need to exaggerate his accomplishments to make a case for him. He’s a crucial link between the bluegrass architects and country music’s present, with an astonishingly diverse body of work to his credit.

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In retrospect, Skaggs’ intersection with the country mainstream looks increasingly like the anomaly in his career – a reality made possible by a brief moment where country radio warmed to performers with a traditional bent, but thrilling nonetheless. His top-notch performance last weekend was a reminder of how much we’re lacking for that skill set in the present.

Now that we’re at a juncture when radio seems to be weighing its options about what sounds will dominate after bro-country, it’s hard not to wonder which bluegrass-steeped performers could find new ways to make it mainstream. There’s Dierks Bentley, a superstar who’s already put out a bluegrass album. There’s Charlie Worsham, a dazzling player and singer. Quickly rising is Carly Pearce, who led a bluegrass band as a teen. And, of course, there’s also Dan Tyminski’s last-name-only solo project Southern Gothic and its futuristic blend of country, bluegrass and spooky electronics. Each one of them has a unique vision of bluegrass-influenced country, something that wouldn’t have been possible without Ricky Skaggs.

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