Country Music Highway consists of the section of U.S. 23 that runs through Kentucky from Ashland south through seven counties before reaching the top of Pound Mountain where it ends at Virginia’s state line.
Kentucky, known for its fast horses and pretty women along with the gold depository at Fort Knox, is geographically divided by its mountainous area in Eastern Kentucky and its low lying hills and rolling meadowlands in the central and western parts of the state.
While the bluegrass section has produced its share of famous thoroughbreds, Eastern Ky. has long been recognized for its roots in mountain music established by the early Scotch-Irish settlers.
The winding mountain roads that lead up hollers such as Butcher Holler near Van Lear where country music star, Loretta Lynn, grew up are plentiful. Lynn’s youngest sister, Crystal Gayle, was born in nearby Paintsville, before her family moved to Indiana when she was four.
Billy Ray Cyrus and The Judds (Naomi, the mother, and Wynonna, her daughter) grew up in or near Ashland, home of the Paramount Art Center, an Art Deco-style movie theatre build in the 1930s that has been converted to a performing arts venue.
Ashland, situated across the Big Sandy River from West Virginia, has long been known as an industrial city, home of Ashland Oil where Ashland High School’s Tomcats have fielded powerful athletic teams that have brought home several state championship trophies.
Cyrus who was vaulted to country music fame by recording such hits as “Ackey Breaky Heart” during the 1990s continues to perform both blues and country music. He has won two Grammys of the seven Grammy nominations he has received.
The Judds rose to national prominence in country music during the mid-1980s by recording such hits as “Girls Night Out,” “Have Mercy” and “Rockin’ with the Rhythm.” The mother-daughter duo won five Grammys of the seven nominations received.
The four-lane drive on U.S. 23 from Ashland to the top of Pound Mountain where General James A. Garfield posted his lookouts during the American Civil War will provide drivers with views of roadside signs that feature the following female country music stars in addition to the Judds: Loretta Lynn, Crystal Gayle, Patty Loveless and Rebecca Lynn Howard.
Male country music stars whose names are featured on special roadside signs beside U.S. 23 in addition to Cyrus are Chris Stapleton, the late Tom T. Hall, Ricky Skaggs, the late Keith Whitley, Dwight Yoakam, the late Frank “Hylo” Brown, Jr., the late Gary Stewart, Bennie Rose, Tyler Childers and Sundy Best, a duo comprised of Kristofer Bentley and Nicholas Jamerson.
Driving south from Ashland, one will pass signs honoring Hall, who was born in Olive Hill; Skaggs, who grew up in Cordell; Stapleton, who is from Staffordsville that has become the home of U.S. 23 Country Music Highway Museum; and Brown, who was born in River and grew up there near Paintsville in Johnson County.
Other signs honor Sundy Best, the duo from Prestonsburg; Rose, from Virgie; Childers, from Paintsville; and Stewart from Jenkins.
Hall, a prolific songwriter who attended Roanoke College via the G.I. bill after he left the U.S. Army that he had joined in 1957, worked as a DJ in Virginia before moving to Nashville where he became a member of the Grand Ole Opry in 1971. Many of his hits, such as “Watermelon Wine,” continue to be played on radio stations today, and his song, “Harper Valley PTA” reached No. 1 on “Billboard Hot 100.” Later, a movie by the same name was made.
Hall passed away on Aug. 20, at 85 in Franklin, Tn., three months after Roanoke College awarded him the honorary degree of Doctor of Fine Arts in May during its commencement ceremonies.
Stapleton, currently one of Nashville’s top recording artists and songwriters, had won four Grammys before winning number five in April when his album, “Starting Over,” was awarded the Best Album.
He is also winner of seven Academy of Country Music (ACM) awards and 10 Country Music Association (CMA) awards.
Skaggs, a household name in bluegrass circles, has won 14 Grammys. He made his debut as a mandolin player and singer at seven, performing with Lester Flatt and Earl Scruggs on television.
Howard was born in Salyersville on April 24, 1979, and she has won two Grammys, recorded seven singles that have charted on “Billboard Hot Country Songs” chart and formed Loving Mary, a country-rock band that she performs with as a vocalist and bassist.
Brown, who preceded all others who are honored by having their names on signage along Country Music Highway, began his career as a country music performer on WCMI Radio in Ashland in 1939. He earned the nickname “Hylo” because of the wide range of his voice.
In 1954, he signed a recording contract with Columbia Records, and by then, he had become a radio-syndicated entertainer who was helping bridge the gap between bluegrass and country music, two related fields of music that he excelled in as a vocalist and musician.
Both Lynn and Gayle rose to fame in country music from humble roots as daughters of a coal miner in Van Lear near Paintsville.
Gayle, who began her career in the 1970s, has won one Grammy and five CMA awards and recorded four songs that reached No. 1 on “Billboard Top 100” chart. She is known for such hits as “Don’t It Make My Brown Eyes Blue.” “Rolling Stone” named her as one of the best 100 female country music vocalists of all time.
Lynn, a super-star of country music, began her career in the 1950s. After marrying at 13 and becoming a mother at 14, she defied all odds by her showing her determination as a songwriter and vocalist to become a country music star. In 1960, she sang on the Grand Ole Opry, and the performance led to her signing a recording contract with Decca Records in Oct. of 1962.
During her career, she won six Grammys, two CMA awards and three ACM awards, and the song she wrote about her father, “Coal Miner’s Daughter,” continues to be played on radio stations across the country. Also, a movie by the same name was made about her rise from poverty to fame.
Tyler Childers, a graduate of Paintsville High School, was nominated for CMA’s Best Country Solo Performance in 2020. He is both a musician and vocalist. His first album, “Purgatory,” led to his recent designation to be honored on a sign beside Country Music Highway.
In Floyd County that borders Johnson County to the south, Yoakam’s parents lived in Betsy Layne and worked at jobs in Pike County, one of the largest counties in the United States. Yoakam was born on Oct. 3, 1956, in Pikeville, but his parents soon moved from Floyd County to Ohio.
Yoakam attended Ohio State University for a while before dropping out and moving to Los Angeles to pursue his career as an entertainer and actor. He has landed roles in “Slingblade,” “Panic Room,” “Wedding Crashers” and “Bandidas.”
Johnny Cash paid tribute to Yoakam by saying that Yoakam, who currently owns a company, Bakersfield Biscuits, and is the winner of two Grammys out of 18 nominations, was his favorite county music performer.
Pikeville, was the home of the McCoys during the Hatfield and McCoy feud. The city that had an entire mountain removed to divert the flow of the Big Sandy River in order to prevent flooding is in Pike County, a border county to West Virginia where the Hatfields lived on the north side of the Tug Fork of the Big Sandy River.
Loveless, who grew up near Pikeville, has been honored by having her name on one of the official roadside signs near the end of Country Music Highway. Should a driver be traveling south near the end of Country Music Highway or near the beginning of Country Music Highway while heading north from Virginia, the names of Stewart, Rose and Loveless on roadside signs will greet them.
Rose, a native of Caney Creek, graduated from Virgie High School in 1976 in Pike County, and as a vocalist and guitarist, he formed his own band, Due South that was inducted on Nov. 23, 2014 into the Atlanta Country Music Hall of Fame.
Just over two years later on Nov. 26, 2016, the same hall of fame inducted him as an individual country music performer
Stewart was born in nearby Jenkins on May 28, 1944, and he played in a number of bands, including Charlie Pride’s band, the Pridesmen. Skilled as a multi-instrument musician, he mastered the piano, bass and guitar.
In 1974, his “Drinkin’ Thing” reached the Top Ten on “Billboard,” and in 1975, he released his first album, “Out of Hand.” The song, “She’s Actin’ Single,”the third and final single released from his album,” charted No. 1 on “Billboard.”
Stewart, 58, died in Fort Pierce, Fla. on Dec. 16, 2003 from a gunshot wound authorities believe was self-inflicted. Many of the songs that he wrote were recorded by other country music stars, songs that became hits for them before he became a successful vocalist and musician on the Nashville scene.
Whitley’s untimely death came at 33 from alcohol poisoning just three weeks before he would have been inducted as a member of The Grand Ole Opry. He had risen to fame during the mid-1980s when he recorded such hits as “Don’t Close Your Eyes.” Born in Sandy Hook, he died as the youngest of those who have passed away and are being honored via signage along Country Music Highway.
At the time of his death, he had been married to Lorrie Morgan for three years. Morgan continues to tour as one of Nashville’s top female vocalists.
Loveless, also a coal miner’s daughter, has won two Grammys out of the 11 nominations that she has received. On June 11, 1988, she was inducted as a member of The Grand Ole Opry, and Lynn was on stage to welcome her as a new member.
Sundy Best, a duo comprised of Kristofer Bentley and Nicholas Jamerson, both from Prestonsburg, was active from 2010 till 2018 when the duo broke up. The duo’s album, “Bring Up the Sun” was released in 2014, and it charted at No. 11 on “Billboard Top Country Albums.”
The duo is eclectic in that Sundy Best performs a blend of Appalachian, country, bluegrass, rock, soul and R&B. In 2020, the duo announced its intention to reunite.
The Kentucky Opry at the Mountain Arts Center in Prestonsburg was formed in 1990. Prestonsburg, the county seat of Floyd County, is situated on U.S. 23 between Paintsville and Pikeville.
The late Billie Jean Osborne, the music teacher at Betsy Layne High School who was a good friend of the Yoakam, founded the Kentucky Opry, and along with Yoakam’s support, she spearheaded the project that resulted in the city building MAC as a home for the Kentucky Opry where a number of those honored on Country Music Highway got their start or have performed.
“Cry Macho,” a movie produced by Clint Eastwood for HBO MAX, will feature Yoakam playing alongside Eastwood. The film is scheduled to be released on Sept. 17.
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