Country Music

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Country Music

THE FATHER HAD THE BAND FIRST. BUT HE HAD THREE KIDS AND A DAY JOB, SO THE MONTGOMERY DREAM PASSED DOWN TO TWO SONS WHO WOULD TAKE DIFFERENT ROADS OUT OF KENTUCKY. Before John Michael Montgomery had “I Swear,” before Eddie Montgomery had Troy Gentry beside him, the music belonged to Harold Montgomery. Harold played guitar and fronted a weekend band called Harold Montgomery and the Kentucky River Express around Lexington dance halls and nightclubs. He even made it onto Ernest Tubb’s record-shop radio show in Nashville. The talent was there. The door was not. Harold had a wife, three children, and a day job he could not just walk away from. So the family band became the training ground. Carol Montgomery, their mother, stepped in on drums when the band needed one. Later, Eddie took over the kit and Carol moved to tambourine. John Michael joined at 15 as a rhythm guitarist and singer. Their sister sang too. The band changed names, played local rooms, and kept the dream close enough for the children to touch. Then the brothers grew into it. John Michael became the ballad voice that country radio carried through the 1990s. Eddie took the rougher road, the barroom road, the Southern-rock road, and later built Montgomery Gentry with Troy. The father never got to leave the day job for Nashville. But years later, his two sons carried the last name farther than the weekend band ever could — one through wedding songs, the other through working-man anthems, both still dragging Kentucky behind every note.

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HAROLD MONTGOMERY HAD THE BAND FIRST — BUT THREE CHILDREN AND A DAY JOB KEPT THE DREAM IN KENTUCKY UNTIL HIS SONS COULD CARRY IT FARTHER.

Before John Michael Montgomery had “I Swear,” the music was already in the house.

Before Eddie Montgomery had Troy Gentry beside him, the last name had already been carried through Kentucky nightclubs by their father.

Harold Montgomery played guitar and fronted a weekend band called Harold Montgomery and the Kentucky River Express around Lexington dance halls and local rooms.

The talent was there.

The timing was not.

Harold Got Close Enough To See The Door

He was not just a father strumming at home.

Harold made it as far as Ernest Tubb’s record-shop radio show in Nashville. That was close enough to feel the dream breathe, but not close enough to change the whole family’s life.

He had a wife.

Three children.

A day job.

The kind of responsibilities that make a man put the guitar back in the case even when part of him still wants to keep driving toward Nashville.

The Family Band Became The School

So the dream stayed local.

Not dead.

Just unfinished.

Carol Montgomery, their mother, stepped in on drums when the band needed one. Later, Eddie took over the kit, and Carol moved to tambourine. Their sister sang too. John Michael joined at 15 as a rhythm guitarist and singer.

The children were not watching music from a distance.

They were inside it.

Learning timing, crowds, songs, load-outs, and how a room feels when real people decide whether the band is worth listening to.

Two Brothers Took The Same House Different Ways

That is where the story splits.

John Michael grew into the smooth ballad voice country radio carried through the 1990s. “Life’s a Dance.” “I Love the Way You Love Me.” “I Swear.” Songs built for slow dances, weddings, and truck radios late at night.

Eddie carried something rougher.

Barrooms.

Southern-rock muscle.

Working-man pride.

The kind of sound that later made sense beside Troy Gentry.

Eddie Did Not Follow His Brother’s Lane

That part matters.

Eddie did not become a second version of John Michael.

He came from the same family stage, but he took a different road out of it. When Montgomery Gentry finally hit with “Hillbilly Shoes,” it did not sound like a polished love ballad from the 1990s.

It sounded louder.

Rougher.

More defiant.

Like Kentucky had kicked the door instead of knocking.

The Father Never Got The Big Exit

Harold Montgomery never became the national star.

He never got to leave the day job behind and turn the weekend band into a country empire under his own name.

But sometimes a dream does not end where the first man has to stop.

Sometimes it waits in the next room.

In this case, it waited in two sons.

What The Montgomery Family Really Leaves Behind

The deepest part of this story is not only that John Michael and Eddie Montgomery both made it.

It is that the road started before either one of them had a hit.

A father with a weekend band.

A mother on drums.

A Kentucky family learning music together.

One son becoming a ballad star.

Another building a rougher duo with Troy Gentry.

And somewhere behind both careers was Harold Montgomery — the man who could not carry the dream all the way to Nashville himself, but kept it close enough for his children to pick up.

One brother sang the slow dance.

One brother sang the working man’s fight.

Both were still carrying their father’s unfinished song.

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Country Music

KIX BROOKS RECORDED “SACRED GROUND” FOR HIS OWN SOLO ALBUM IN 1989. THE RECORD DEAL WENT NOWHERE. THREE YEARS LATER, ANOTHER BAND RECORDED HIS SONG — AND TOOK IT TO NO. 2. Before Ronnie Dunn, Kix Brooks had already spent years trying to make Nashville work. He moved there in 1979 and discovered fairly quickly that his songs were getting farther than his voice. John Conlee took Brooks’ “I’m Only in It for the Love” to No. 1 in 1983. Two years later, the Nitty Gritty Dirt Band did the same with “Modern Day Romance.” Brooks still wanted his own recording career. An early deal with Avion Records collapsed when the label went bankrupt. Then Capitol Nashville gave him another chance. In 1989, he released the self-titled album Kix Brooks. One of its singles was “Sacred Ground,” written by Brooks with Vernon Rust. It didn’t break him. Brooks later remembered hearing from radio stations that Capitol wasn’t really working the record. He went directly to label executive Jim Foglesong’s successor, Jimmy Bowen? Actually Brooks identifies label head Jim Ed Norman? No—his own recollection names Mr. Crutchfield, and says the executive admitted he simply didn’t understand what Brooks was doing. Brooks’ response was unusual for someone still chasing his first major solo success. He essentially said: then let’s shake hands and part ways. His reasoning was practical. He was a songwriter. He didn’t want good songs climbing only into the lower reaches of the chart and dying because the label wasn’t committed to them. Not long afterward, Tim DuBois heard Brooks’ work and introduced him to Ronnie Dunn. Brooks & Dunn formed in 1990. Their first four singles became No. 1 country hits, and the solo career Brooks had spent years trying to establish was suddenly irrelevant. But “Sacred Ground” wasn’t finished. MCA’s McBride & the Ride recorded it for their second album in 1992, with Tony Brown and Steve Gibson producing. This time radio responded. Their recording climbed to No. 2 on Billboard’s country chart, becoming McBride & the Ride’s highest-charting Billboard single. The album Sacred Ground went gold and produced two additional Top 5 singles. The timing created a strange Nashville reversal. While Kix Brooks was becoming one half of the hottest new duo in country music, another band was simultaneously having its biggest hit with a song left behind by the solo career that hadn’t worked. Years later, Brooks could look back at that Capitol album differently. The artist on its cover never became the star he’d intended. But one of its songs did eventually find the audience it had missed the first time.

Country Music

DAVID BELLAMY WROTE A THREE-MILLION-SELLING HIT FOR ANOTHER MAN BEFORE THE BELLAMY BROTHERS HAD ONE RECORD OF THEIR OWN. Before the duo had a national hit, David Bellamy was writing songs between gigs and long drives. One of them was “Spiders & Snakes,” a strange, playful song that landed with singer Jim Stafford. Stafford recorded it. The record became a major hit and sold more than three million copies. David had not become a star from it. His name was on the writing side, not on the front of the record. But the success changed what was possible. It brought David and Howard closer to Los Angeles, where the brothers suddenly had access to producers, musicians, and rooms that had been far beyond two Florida performers playing regional shows. They entered a scene crowded with singer-songwriters and country-rock musicians — the world around Poco, the Byrds, James Taylor, Van Morrison, and Bob Dylan. The Bellamys were still outsiders, but now they were standing close enough to see how records got made and how one song could move a life. That connection mattered a few years later. When “Let Your Love Flow” finally reached them, David and Howard were ready. They had the studio contacts, the confidence, and a sound of their own. In 1976, the song became a No. 1 pop hit and carried the brothers far beyond Florida. But the first real opening had come from a song they did not get to sing themselves. David wrote the key. Someone else turned it first.

Country Music

MARTY STUART WAS 13 WHEN HE GOT OFF A GREYHOUND BUS IN NASHVILLE. THE NEXT DAY HE CLIMBED ON LESTER FLATT’S TOUR BUS. BY THE END OF THE WEEKEND, HE HAD A JOB PLAYING WITH A COUNTRY MUSIC LEGEND. On August 3, 1972, Marty Stuart stepped off a bus in downtown Nashville from Mississippi. He was thirteen years old. Stuart had already learned guitar and mandolin and played with the Sullivan Family, but Nashville was still something he knew mostly from records and Grand Ole Opry broadcasts. Early that morning, he walked to the Ryman Auditorium before the city had fully come alive. Bluegrass musician Roland White soon picked him up in a 1965 Chevrolet Impala. The next day, White took Stuart to Lester Flatt’s tour bus in Hendersonville. They headed to a bluegrass festival in Delaware, where the teenager was given a chance to play with Flatt’s band. Flatt heard enough. By the end of the weekend, he wanted Stuart in the Nashville Grass permanently. After arrangements were made with his parents, Stuart joined the road at an age when most musicians were still learning songs in bedrooms and school gyms. A week later, he made his first appearance on the Grand Ole Opry. Stuart stayed with Flatt through most of the 1970s. The education happened night after night: long bus rides, festival stages, dressing rooms, radio appearances and hours beside musicians who had helped build bluegrass and country before he was born. When Flatt’s health declined and the band ended, Stuart moved on. He worked with Doc Watson and other musicians, then joined Johnny Cash’s band in 1980. Only later did he build a solo career of his own. “Crying, Waiting, Hoping,” “Hillbilly Rock,” “Tempted,” and his recordings with Travis Tritt helped turn Stuart from respected sideman into a country star. In 1992, he became a member of the Grand Ole Opry. In 2020, he was elected to the Country Music Hall of Fame. But those early years with Flatt left another mark. Stuart began saving the instruments, photographs, stage clothes and personal objects that passed through the country world around him. What started as a young musician holding onto pieces of his heroes eventually grew into one of the most important private collections of country-music history. The road job Lester Flatt gave him taught Stuart how to play the music. It also taught him how quickly the people and objects that made it could disappear.

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Country Music

KIX BROOKS RECORDED “SACRED GROUND” FOR HIS OWN SOLO ALBUM IN 1989. THE RECORD DEAL WENT NOWHERE. THREE YEARS LATER, ANOTHER BAND RECORDED HIS SONG — AND TOOK IT TO NO. 2. Before Ronnie Dunn, Kix Brooks had already spent years trying to make Nashville work. He moved there in 1979 and discovered fairly quickly that his songs were getting farther than his voice. John Conlee took Brooks’ “I’m Only in It for the Love” to No. 1 in 1983. Two years later, the Nitty Gritty Dirt Band did the same with “Modern Day Romance.” Brooks still wanted his own recording career. An early deal with Avion Records collapsed when the label went bankrupt. Then Capitol Nashville gave him another chance. In 1989, he released the self-titled album Kix Brooks. One of its singles was “Sacred Ground,” written by Brooks with Vernon Rust. It didn’t break him. Brooks later remembered hearing from radio stations that Capitol wasn’t really working the record. He went directly to label executive Jim Foglesong’s successor, Jimmy Bowen? Actually Brooks identifies label head Jim Ed Norman? No—his own recollection names Mr. Crutchfield, and says the executive admitted he simply didn’t understand what Brooks was doing. Brooks’ response was unusual for someone still chasing his first major solo success. He essentially said: then let’s shake hands and part ways. His reasoning was practical. He was a songwriter. He didn’t want good songs climbing only into the lower reaches of the chart and dying because the label wasn’t committed to them. Not long afterward, Tim DuBois heard Brooks’ work and introduced him to Ronnie Dunn. Brooks & Dunn formed in 1990. Their first four singles became No. 1 country hits, and the solo career Brooks had spent years trying to establish was suddenly irrelevant. But “Sacred Ground” wasn’t finished. MCA’s McBride & the Ride recorded it for their second album in 1992, with Tony Brown and Steve Gibson producing. This time radio responded. Their recording climbed to No. 2 on Billboard’s country chart, becoming McBride & the Ride’s highest-charting Billboard single. The album Sacred Ground went gold and produced two additional Top 5 singles. The timing created a strange Nashville reversal. While Kix Brooks was becoming one half of the hottest new duo in country music, another band was simultaneously having its biggest hit with a song left behind by the solo career that hadn’t worked. Years later, Brooks could look back at that Capitol album differently. The artist on its cover never became the star he’d intended. But one of its songs did eventually find the audience it had missed the first time.

Country Music

DAVID BELLAMY WROTE A THREE-MILLION-SELLING HIT FOR ANOTHER MAN BEFORE THE BELLAMY BROTHERS HAD ONE RECORD OF THEIR OWN. Before the duo had a national hit, David Bellamy was writing songs between gigs and long drives. One of them was “Spiders & Snakes,” a strange, playful song that landed with singer Jim Stafford. Stafford recorded it. The record became a major hit and sold more than three million copies. David had not become a star from it. His name was on the writing side, not on the front of the record. But the success changed what was possible. It brought David and Howard closer to Los Angeles, where the brothers suddenly had access to producers, musicians, and rooms that had been far beyond two Florida performers playing regional shows. They entered a scene crowded with singer-songwriters and country-rock musicians — the world around Poco, the Byrds, James Taylor, Van Morrison, and Bob Dylan. The Bellamys were still outsiders, but now they were standing close enough to see how records got made and how one song could move a life. That connection mattered a few years later. When “Let Your Love Flow” finally reached them, David and Howard were ready. They had the studio contacts, the confidence, and a sound of their own. In 1976, the song became a No. 1 pop hit and carried the brothers far beyond Florida. But the first real opening had come from a song they did not get to sing themselves. David wrote the key. Someone else turned it first.

Country Music

MARTY STUART WAS 13 WHEN HE GOT OFF A GREYHOUND BUS IN NASHVILLE. THE NEXT DAY HE CLIMBED ON LESTER FLATT’S TOUR BUS. BY THE END OF THE WEEKEND, HE HAD A JOB PLAYING WITH A COUNTRY MUSIC LEGEND. On August 3, 1972, Marty Stuart stepped off a bus in downtown Nashville from Mississippi. He was thirteen years old. Stuart had already learned guitar and mandolin and played with the Sullivan Family, but Nashville was still something he knew mostly from records and Grand Ole Opry broadcasts. Early that morning, he walked to the Ryman Auditorium before the city had fully come alive. Bluegrass musician Roland White soon picked him up in a 1965 Chevrolet Impala. The next day, White took Stuart to Lester Flatt’s tour bus in Hendersonville. They headed to a bluegrass festival in Delaware, where the teenager was given a chance to play with Flatt’s band. Flatt heard enough. By the end of the weekend, he wanted Stuart in the Nashville Grass permanently. After arrangements were made with his parents, Stuart joined the road at an age when most musicians were still learning songs in bedrooms and school gyms. A week later, he made his first appearance on the Grand Ole Opry. Stuart stayed with Flatt through most of the 1970s. The education happened night after night: long bus rides, festival stages, dressing rooms, radio appearances and hours beside musicians who had helped build bluegrass and country before he was born. When Flatt’s health declined and the band ended, Stuart moved on. He worked with Doc Watson and other musicians, then joined Johnny Cash’s band in 1980. Only later did he build a solo career of his own. “Crying, Waiting, Hoping,” “Hillbilly Rock,” “Tempted,” and his recordings with Travis Tritt helped turn Stuart from respected sideman into a country star. In 1992, he became a member of the Grand Ole Opry. In 2020, he was elected to the Country Music Hall of Fame. But those early years with Flatt left another mark. Stuart began saving the instruments, photographs, stage clothes and personal objects that passed through the country world around him. What started as a young musician holding onto pieces of his heroes eventually grew into one of the most important private collections of country-music history. The road job Lester Flatt gave him taught Stuart how to play the music. It also taught him how quickly the people and objects that made it could disappear.

Country Music

JOE DIFFIE HAD BEEN OFF THE CENTER OF COUNTRY RADIO FOR YEARS. THEN JASON ALDEAN RELEASED A SONG THAT HAD AN ENTIRE NEW GENERATION CHANTING HIS NAME. In 1994, Joe Diffie was near the height of his career. “Third Rock from the Sun” reached No. 1. Then “Pickup Man” followed and stayed there four weeks. Jason Aldean was still a high-school junior in Georgia, listening to Diffie and playing songs from that era before his own career existed. Aldean later remembered attending a Macon festival where roughly 5,000 people gathered for Diffie while only a few hundred watched a young Kenny Chesney on another stage. Almost two decades passed. By 2012, Aldean had become one of country music’s biggest stars. Songwriters Thomas Rhett, Luke Laird and Barry Dean were working on another song when the session changed direction. They built a track around 1990s nostalgia, filling it with references to Diffie records including “Pickup Man,” “John Deere Green,” “Third Rock from the Sun” and “Honky Tonk Attitude.” They called it “1994.” Aldean heard the demo while songs were being pitched for him and asked to hear it again. Soon afterward, he recorded it for Night Train. It became the album’s third single in March 2013. Diffie had nothing to do with making the record. Then he heard what they had done. His name had become the chant at the center of the song. Diffie said he was initially stunned, then realized what it meant: thousands of younger Aldean fans would suddenly be shouting the name of a singer whose biggest records had been released when many of them were children—or not yet born. The effect followed him off the radio. Diffie later said younger people began showing up at his concerts wanting to find out who the man from “1994” actually was. What surprised him even more was that many had gone backward into his catalog and learned the older songs. He called the attention a “shot in the arm.” Aldean had grown up playing Joe Diffie songs in Georgia clubs. Years later, some of Aldean’s own fans discovered those same records by moving in the opposite direction—starting with Jason Aldean and working their way back to Joe.