Ricky Skaggs Will The Circle Be Unbroken

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“Scroll down to the end of the article to listen to music.”

Introduction

There are songs that entertain, songs that inspire, and then there are songs that feel like they’re stitched into the very fabric of life. Will The Circle Be Unbroken is one of those. It’s more than a song—it’s a thread that connects past to present, earth to heaven, and sorrow to hope.

This gospel hymn has been sung by countless voices, from country legends like Johnny Cash and The Carter Family to bluegrass pioneers and church choirs around the world. It’s a song of mourning, yes, but also one of deep, unshakable faith. At its core, it’s a question—will the circle be unbroken?—that resonates with anyone who has ever lost someone they love.

With its simple yet powerful lyrics, the song paints the picture of a funeral procession, a loved one being carried away, and the aching question of whether we’ll see them again in that “better home awaiting in the sky.” But what makes this song truly special is the way it turns grief into reassurance. It reminds us that love and faith can transcend even death, that the circle of life, of family, and of music itself never truly breaks.

Over the years, Will The Circle Be Unbroken has become more than just a gospel standard—it’s an anthem of unity. The song took on a whole new life in 1972 when the Nitty Gritty Dirt Band collaborated with country and bluegrass greats to record an album by the same name. That version wasn’t just about faith—it was about bridging generations of musicians, preserving tradition, and passing the torch of music from one hand to the next.

Whether it’s sung in a quiet church, at a funeral, or belted out at a bluegrass festival, this song has an uncanny way of bringing people together. It’s a reminder that even in our sorrow, we are not alone. The ones we’ve lost are never truly gone, and someday, somewhere, we just might meet again—singing together in perfect harmony

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“HILLBILLY SHOES” STARTED AS SOMETHING CLOSER TO BLUEGRASS. MONTGOMERY GENTRY TOOK IT INTO A KENTUCKY BASEMENT, TURNED UP THE GUITARS — AND USED IT TO BREAK OPEN COUNTRY RADIO. Before Columbia knew exactly what to do with Eddie Montgomery and Troy Gentry, label people came to Lexington and listened to them where the music already lived. According to longtime band member Bo Garrett, representatives from Nashville sat in the basement of Troy Gentry’s mother’s house with a small handheld recorder while the group worked through songs that would become Tattoos & Scars. One of them was “Hillbilly Shoes.” The demo they had received was not built around the hard guitar attack listeners would later recognize. It was much closer to bluegrass. That mattered because Montgomery Gentry were arriving at an awkward moment for that kind of sound. By 1999, country radio was packed with polished crossover records. Eddie and Troy wanted something rougher — Merle Haggard and George Jones on one side, Lynyrd Skynyrd and Charlie Daniels on the other. Eddie told Radio & Records they wanted Nashville to let them be themselves: no smoothing, no “doctoring,” just the music they already played in Kentucky bars. Producer Joe Scaife largely let them have it. “Hillbilly Shoes” came out with sawing fiddle, a heavy guitar riff and enough rock weight to separate the duo immediately from the softer end of late-’90s country. Radio reacted before the machinery was ready: the single entered Billboard’s country chart two weeks ahead of its scheduled release, and demand became strong enough for Columbia to move Tattoos & Scars forward to April 6, 1999. The album did not abandon traditional country to get there. “Lonely and Gone” carried an older honky-tonk ache. “Daddy Won’t Sell the Farm” put rural resistance against suburban expansion. Charlie Daniels himself appeared on “All Night Long.” Critics heard Marshall Tucker and Southern rock, but also Haggard, Jones, Hank Williams and Dwight Yoakam underneath the volume. A year later, the consequence became unmistakable. At the 2000 CMA Awards, Montgomery Gentry won Vocal Duo of the Year, ending Brooks & Dunn’s eight-year hold on the category. That trophy was bigger than one successful debut. A bluegrass-leaning demo had passed through a Kentucky basement, acquired electric teeth, and helped make room on mainstream country radio for a sound that would become increasingly familiar in the decade ahead — country music with mud on its boots and Southern rock still humming through the amplifiers.

THREE WEEKS AFTER BURYING HIS 13-YEAR-OLD DAUGHTER, GEORGE STRAIT WAS BACK ONSTAGE. MONTHS LATER, WHEN HE FINALLY AGREED TO SPEAK TO REPORTERS AGAIN, THERE WAS ONE CONDITION: NO QUESTIONS ABOUT THE ACCIDENT. By the summer of 1986, Strait’s career was accelerating faster than at any point before it. He had just won CMA Male Vocalist of the Year and Album of the Year, his crowds were growing, and he later remembered working close to 200 dates a year. The quiet Texas singer who had broken through only five years earlier was becoming one of country music’s biggest stars. Then, late on June 25, his daughter Jenifer went riding with three teenage friends near San Marcos, Texas. Shortly before midnight, their car entered a sharp turn at excessive speed, skidded sideways and overturned into a ditch. Jenifer, thirteen, was partially thrown from the vehicle and died at the scene. The other occupants survived. Alcohol was not considered a factor. Strait had been away working when it happened. The touring stopped, but not for long. According to a later Country Music Hall of Fame profile, he returned to the stage roughly three weeks after Jenifer’s death, carrying on through a schedule that had already been relentless before his family’s life changed overnight. What changed more permanently was his relationship with the public. For several months he stopped speaking to the press altogether. When interviews resumed, reporters were told that questions about Jenifer and the accident were off limits. The man whose career was becoming increasingly visible began guarding his private life with unusual intensity—a boundary that would remain part of George Strait’s public image for decades. That October, the industry placed him back under its brightest lights. Strait won CMA Male Vocalist of the Year for the second consecutive year. This time, he accepted the award in Jenifer’s memory. The family also created the Jenifer Strait Memorial Foundation, directing support toward children’s charities. Nearly four decades later, the foundation was still active, helping organizations that serve children’s emotional, educational and medical needs. George Strait’s career did not slow after 1986; commercially, it became even larger. But something else had quietly disappeared that summer. The increasingly famous singer would continue giving audiences records, concerts and awards for decades, while keeping one room of his life firmly behind a closed door. Jenifer’s name remained outside that door—not in interviews, but in the foundation that continued helping other children.

BY 1995, COUNTRY RADIO HAD MOSTLY STOPPED CALLING EMMYLOU HARRIS. SO INSTEAD OF TRYING TO SOUND YOUNGER, SHE HIRED THE PRODUCER BEHIND U2 AND BOB DYLAN — AND MADE ONE OF THE MOST IMPORTANT RECORDS OF HER CAREER. Emmylou Harris was 48, deeply respected and increasingly absent from mainstream country radio. Her 1993 album Cowgirl’s Prayer had failed to produce a Top 40 country single, and Harris understood what was happening. Years later, she described it plainly: she was no longer being invited to the party. Rather than chase whatever Nashville programmers wanted next, Elektra gave her unusual freedom to choose her own direction. Her answer was Daniel Lanois. Lanois was hardly the obvious Nashville choice. He had built atmospheric records with U2, Peter Gabriel and Bob Dylan, and Harris had become fascinated with both his solo album Acadie and Dylan’s Oh Mercy. She did not know exactly what kind of record they would make. That uncertainty was part of the appeal. They began building Wrecking Ball around texture rather than conventional country polish. The sessions moved through New Orleans, Nashville and San Francisco. Reverb hung around Harris’ voice. Percussion became heavier. Electric guitars drifted in and out of the arrangements. U2 drummer Larry Mullen Jr. played on the record, while Neil Young, Steve Earle, Lucinda Williams and others entered the project from different corners of American roots music. Harris even recorded Jimi Hendrix’s “May This Be Love” alongside songs by Dylan, Young and Gillian Welch. For listeners who knew her from “Together Again,” “Blue Kentucky Girl” or the Hot Band, the sound could feel almost disorienting. But the roots had not disappeared. Country, folk, gospel and bluegrass were still underneath the record; Lanois had simply changed the air around them. That distinction mattered. Wrecking Ball was not Harris abandoning country so much as demonstrating how far its emotional language could travel once the usual studio rules were removed. The album won the 1996 Grammy for Best Contemporary Folk Album and became a major artistic turning point for Harris. More importantly, its mixture of country tradition, singer-songwriter material and experimental production arrived just as the modern Americana movement was beginning to take shape. Three decades later, the Recording Academy selected Wrecking Ball for the Grammy Hall of Fame. By then, the record had acquired a significance no radio programmer could have measured in 1995. Harris had been pushed toward the edge of mainstream country. From there, she helped show an entire generation of roots musicians how much territory existed beyond it.

“HILLBILLY SHOES” STARTED AS SOMETHING CLOSER TO BLUEGRASS. MONTGOMERY GENTRY TOOK IT INTO A KENTUCKY BASEMENT, TURNED UP THE GUITARS — AND USED IT TO BREAK OPEN COUNTRY RADIO. Before Columbia knew exactly what to do with Eddie Montgomery and Troy Gentry, label people came to Lexington and listened to them where the music already lived. According to longtime band member Bo Garrett, representatives from Nashville sat in the basement of Troy Gentry’s mother’s house with a small handheld recorder while the group worked through songs that would become Tattoos & Scars. One of them was “Hillbilly Shoes.” The demo they had received was not built around the hard guitar attack listeners would later recognize. It was much closer to bluegrass. That mattered because Montgomery Gentry were arriving at an awkward moment for that kind of sound. By 1999, country radio was packed with polished crossover records. Eddie and Troy wanted something rougher — Merle Haggard and George Jones on one side, Lynyrd Skynyrd and Charlie Daniels on the other. Eddie told Radio & Records they wanted Nashville to let them be themselves: no smoothing, no “doctoring,” just the music they already played in Kentucky bars. Producer Joe Scaife largely let them have it. “Hillbilly Shoes” came out with sawing fiddle, a heavy guitar riff and enough rock weight to separate the duo immediately from the softer end of late-’90s country. Radio reacted before the machinery was ready: the single entered Billboard’s country chart two weeks ahead of its scheduled release, and demand became strong enough for Columbia to move Tattoos & Scars forward to April 6, 1999. The album did not abandon traditional country to get there. “Lonely and Gone” carried an older honky-tonk ache. “Daddy Won’t Sell the Farm” put rural resistance against suburban expansion. Charlie Daniels himself appeared on “All Night Long.” Critics heard Marshall Tucker and Southern rock, but also Haggard, Jones, Hank Williams and Dwight Yoakam underneath the volume. A year later, the consequence became unmistakable. At the 2000 CMA Awards, Montgomery Gentry won Vocal Duo of the Year, ending Brooks & Dunn’s eight-year hold on the category. That trophy was bigger than one successful debut. A bluegrass-leaning demo had passed through a Kentucky basement, acquired electric teeth, and helped make room on mainstream country radio for a sound that would become increasingly familiar in the decade ahead — country music with mud on its boots and Southern rock still humming through the amplifiers.

THREE WEEKS AFTER BURYING HIS 13-YEAR-OLD DAUGHTER, GEORGE STRAIT WAS BACK ONSTAGE. MONTHS LATER, WHEN HE FINALLY AGREED TO SPEAK TO REPORTERS AGAIN, THERE WAS ONE CONDITION: NO QUESTIONS ABOUT THE ACCIDENT. By the summer of 1986, Strait’s career was accelerating faster than at any point before it. He had just won CMA Male Vocalist of the Year and Album of the Year, his crowds were growing, and he later remembered working close to 200 dates a year. The quiet Texas singer who had broken through only five years earlier was becoming one of country music’s biggest stars. Then, late on June 25, his daughter Jenifer went riding with three teenage friends near San Marcos, Texas. Shortly before midnight, their car entered a sharp turn at excessive speed, skidded sideways and overturned into a ditch. Jenifer, thirteen, was partially thrown from the vehicle and died at the scene. The other occupants survived. Alcohol was not considered a factor. Strait had been away working when it happened. The touring stopped, but not for long. According to a later Country Music Hall of Fame profile, he returned to the stage roughly three weeks after Jenifer’s death, carrying on through a schedule that had already been relentless before his family’s life changed overnight. What changed more permanently was his relationship with the public. For several months he stopped speaking to the press altogether. When interviews resumed, reporters were told that questions about Jenifer and the accident were off limits. The man whose career was becoming increasingly visible began guarding his private life with unusual intensity—a boundary that would remain part of George Strait’s public image for decades. That October, the industry placed him back under its brightest lights. Strait won CMA Male Vocalist of the Year for the second consecutive year. This time, he accepted the award in Jenifer’s memory. The family also created the Jenifer Strait Memorial Foundation, directing support toward children’s charities. Nearly four decades later, the foundation was still active, helping organizations that serve children’s emotional, educational and medical needs. George Strait’s career did not slow after 1986; commercially, it became even larger. But something else had quietly disappeared that summer. The increasingly famous singer would continue giving audiences records, concerts and awards for decades, while keeping one room of his life firmly behind a closed door. Jenifer’s name remained outside that door—not in interviews, but in the foundation that continued helping other children.

BY 1995, COUNTRY RADIO HAD MOSTLY STOPPED CALLING EMMYLOU HARRIS. SO INSTEAD OF TRYING TO SOUND YOUNGER, SHE HIRED THE PRODUCER BEHIND U2 AND BOB DYLAN — AND MADE ONE OF THE MOST IMPORTANT RECORDS OF HER CAREER. Emmylou Harris was 48, deeply respected and increasingly absent from mainstream country radio. Her 1993 album Cowgirl’s Prayer had failed to produce a Top 40 country single, and Harris understood what was happening. Years later, she described it plainly: she was no longer being invited to the party. Rather than chase whatever Nashville programmers wanted next, Elektra gave her unusual freedom to choose her own direction. Her answer was Daniel Lanois. Lanois was hardly the obvious Nashville choice. He had built atmospheric records with U2, Peter Gabriel and Bob Dylan, and Harris had become fascinated with both his solo album Acadie and Dylan’s Oh Mercy. She did not know exactly what kind of record they would make. That uncertainty was part of the appeal. They began building Wrecking Ball around texture rather than conventional country polish. The sessions moved through New Orleans, Nashville and San Francisco. Reverb hung around Harris’ voice. Percussion became heavier. Electric guitars drifted in and out of the arrangements. U2 drummer Larry Mullen Jr. played on the record, while Neil Young, Steve Earle, Lucinda Williams and others entered the project from different corners of American roots music. Harris even recorded Jimi Hendrix’s “May This Be Love” alongside songs by Dylan, Young and Gillian Welch. For listeners who knew her from “Together Again,” “Blue Kentucky Girl” or the Hot Band, the sound could feel almost disorienting. But the roots had not disappeared. Country, folk, gospel and bluegrass were still underneath the record; Lanois had simply changed the air around them. That distinction mattered. Wrecking Ball was not Harris abandoning country so much as demonstrating how far its emotional language could travel once the usual studio rules were removed. The album won the 1996 Grammy for Best Contemporary Folk Album and became a major artistic turning point for Harris. More importantly, its mixture of country tradition, singer-songwriter material and experimental production arrived just as the modern Americana movement was beginning to take shape. Three decades later, the Recording Academy selected Wrecking Ball for the Grammy Hall of Fame. By then, the record had acquired a significance no radio programmer could have measured in 1995. Harris had been pushed toward the edge of mainstream country. From there, she helped show an entire generation of roots musicians how much territory existed beyond it.

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BY 1991, MARK O’CONNOR HAD PLAYED ON SO MANY NASHVILLE RECORDS THAT HIS FIDDLE WAS EVERYWHERE — EVEN WHEN HIS NAME WASN’T. SO HE MADE AN ALBUM THAT TURNED THE SESSION PLAYERS THEMSELVES INTO THE MAIN EVENT. Country music was entering one of its biggest commercial eras. Garth Brooks was exploding, Vince Gill was breaking through, and a new generation of singers was filling radio. But behind many of those records sat another cast of musicians whose names rarely reached the audience. O’Connor knew that world from the inside. By his twenties, he had become one of Nashville’s most in-demand players, moving between fiddle, guitar and mandolin sessions while working beside musicians such as Jerry Douglas, Brent Mason, Paul Franklin, Eddie Bayers, Matt Rollings and Roy Huskey Jr. They were the people producers called when a record needed a particular feel, a certain lick, or a part that had to be right before the clock ran out. In 1991, O’Connor decided those players deserved more than another line of small-print credits. He gathered more than fifty Nashville musicians for The New Nashville Cats, deliberately building the album around the instrumental side of the recording scene. Bluegrass sat beside western swing, country beside jazz and rockabilly. On “Restless,” even Vince Gill, Ricky Skaggs and Steve Wariner stepped in — not to dominate the record, but to become part of the larger musical community O’Connor was documenting. The title carried its own piece of history. “The Nashville Cats” had already become shorthand for the city’s frighteningly good studio players after the Lovin’ Spoonful celebrated them in the 1960s. O’Connor’s version was effectively saying: another generation had arrived, and these were the hands now shaping the records America was hearing. The industry noticed. At the 1991 CMA Awards, O’Connor was named Musician of the Year, while Mark O’Connor & The New Nashville Cats won Vocal Event of the Year. The album later earned the Grammy for Best Country Instrumental Performance, and “Restless” won Best Country Collaboration with Vocals. Those trophies mattered for a reason larger than one fiddler. Country music history is usually remembered through voices: the singer, the song, the star standing beneath the spotlight. The New Nashville Cats preserved something easier to lose — the sound of the room behind them. And for once, the musicians who normally disappeared when the singer’s name went on the cover had an album with enough room for people to learn theirs.