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In 1937, a cheap Sears and Roebuck catalog guitar arrived at a ferryman’s porch in Friars Point, Mississippi, for a four-year-old boy named Harold Lloyd Jenkins. The country was deep in the Great Depression, and the boy’s father, Floyd Jenkins, earned a modest living operating a ferry across the Mississippi River. Saving enough money to order an acoustic instrument through the mail meant trading away practical necessities for a household belief in a toddler’s ear. When Harold sat down with the full-sized guitar, its wooden body nearly hid his small frame, and his fingers could barely reach across the fretboard. Out on the front porch, his grandfather and his father patiently guided his hands through his first chords while steamboat whistles echoed off the water and the Saturday night Grand Ole Opry played through a battery-powered radio. Growing up in the Mississippi Delta, the boy also listened closely to local acoustic blues players and gospel choirs, absorbing the raw vocal grit that would define his adult voice. By age ten, after the family moved across the river to Helena, Arkansas, Harold used those early lessons to form his first band, the Phillips County Ramblers, and host a live Saturday morning show on radio station KFFA. Even when a contract offer from the Philadelphia Phillies and army service in Japan pulled him toward other paths, the habit formed on that oversized Sears guitar brought him back to music. Taking the stage name Conway Twitty, he turned that childhood foundation into a four-decade career with fifty-five Billboard number-one country hits and over sixty-five chart-toppers overall. Through all the years of sold-out arenas and his own Twitty City complex near Nashville, he still credited his ferryman father, his grandfather, and those afternoon lessons on the Friars Point porch for every note that followed.

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In 1937, riverboat pilot Floyd Jenkins ordered a mail-order guitar from the Sears and Roebuck catalog for his four-year-old son in Friars Point, Mississippi.

Born on September 1, 1933, to Floyd and Velma Jenkins, Harold Lloyd Jenkins received his first and middle names from a great-uncle who admired the silent film comedian Harold Lloyd. During the Great Depression, Floyd supported the household by farming cotton and piloting a small passenger ferry across the Mississippi River between Friars Point and Helena, Arkansas.

Money was scarce along the Coahoma County riverfront, and ordering an instrument through the mail required setting aside cash that would otherwise go toward household basics. When the full-sized acoustic guitar arrived on the front porch, its wooden body nearly hid the four-year-old’s frame, and his fingers could barely span the frets.

Out on that porch, Floyd and the boy’s maternal grandfather sat with him after ferry runs, placing his fingers on the neck until he could form his first chords. Before Harold was old enough to attend school, he was accompanying his father on the riverboat and carrying tunes he had learned at home.

Those afternoon lessons took place inside a rich Mississippi Delta musical environment. Every Saturday night, the Jenkins family gathered around a battery-powered radio to listen to the Grand Ole Opry broadcast out of Nashville, while daytime walks near the levee brought the sound of local acoustic blues players and African American gospel choirs.

In 1943, when Harold was ten years old, the Jenkins family moved permanently across the river to Helena, Arkansas. Within two years of settling on the west bank, he teamed up with neighborhood classmates to form his first country group, the Phillips County Ramblers.

Among his seventh-grade classmates and fellow band members was John Hughey, a young musician from nearby Elaine, Arkansas, who had also learned to play on a Sears acoustic guitar at age nine before switching to lap steel. Together with their school friends, the teenagers earned a regular Saturday morning broadcast slot on Helena radio station KFFA.

KFFA was already famous across the region as the home of *King Biscuit Time*, the daily midday broadcast featuring blues harmonica player Sonny Boy Williamson II and the King Biscuit Boys. Sharing station studios and local airwaves with working Delta blues musicians gave the young singer early microphone experience and a vocal phrasing steeped in both country ballads and rhythm and blues.

For a brief period after high school, athletics and military service pulled him away from Arkansas radio. Having graduated with a .450 batting average, Jenkins accepted a professional baseball contract offer from the Philadelphia Phillies, only to receive his draft notice from the United States Army before he could report to the team.

Stationed in Japan during the mid-1950s, he picked up his guitar again and organized a military band called the Cimarrons, playing country shows for fellow soldiers across service clubs. Discharged in 1956, he returned to the Mid-South, recorded early rockabilly sessions at Sun Studio in Memphis, and adopted the stage name Conway Twitty in 1957 after spotting Conway, Arkansas, and Twitty, Texas, on a road map.

Although his 1958 crossover hit “It’s Only Make Believe” turned him into an international pop and rock attraction for nearly a decade, he continued writing country songs in hotel rooms between rockabilly bookings. In 1965, partway through a nightclub set in New Jersey, he set down his guitar, walked off the stage, and left rock music behind to sing country full-time in Nashville.

The transition started slowly as several country radio programmers hesitated to play a former teen idol, leaving his 1966 country chart debut at number eighteen. When he finally reached number one on the Billboard country chart with “Next in Line” in November 1968, he called back to his Arkansas school days and hired his old Phillips County Ramblers bandmate John Hughey to play pedal steel guitar.

Hughey stayed in the band for the next twenty years, playing the signature high-register steel intro on 1970’s “Hello Darlin'” as Twitty accumulated forty Billboard number-one country hits and fifty-five number-one singles across all trade charts. Back in Mississippi, Floyd and Velma Jenkins remained close to the music as well, operating a supper club called Conway’s on Moon Lake near Friars Point.

Decades after the mail-order guitar arrived on the riverfront porch in 1937, the ferryman’s son was walking onto arena stages across North America with his seventh-grade bandmate from Helena playing steel guitar right behind him.

https://www.youtube.com/watch?v=d7FspsAHqfQ

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A polite hello from a former girlfriend on a street in Odessa, Texas broke through Roy Orbison’s quiet composure and inspired his 1961 classic, “Crying.” Raised around the oil fields of Wink and Odessa, Orbison grew up in a West Texas culture that taught men to keep their hurt to themselves. After a painful breakup, he let friends and family believe he had moved on, until he crossed paths with her in town. Shaken by her calm, distant greeting, he went straight to his songwriting partner, Joe Melson. The two turned that moment into a ballad about a man who thinks he is over a breakup until seeing her again brings everything back. In July 1961, Orbison recorded the track at RCA Studio B in Nashville with Monument Records producer Fred Foster, an orchestra, and the Anita Kerr Singers. The melody climbed across two and a half octaves to a soaring final note, forcing engineer Bill Porter to position Orbison at a careful distance on the studio floor so the full force of his voice would not overload the microphone. Released that August, “Crying” sold over a million copies, hitting No. 1 on the Cashbox chart and No. 2 on the Billboard Hot 100 behind Ray Charles’s “Hit the Road Jack.” In an era when male singers were expected to project tough confidence, Orbison stood still behind his dark glasses and let listeners hear a grown man break down. Elvis Presley later called him the greatest singer in the world. After Orbison lost his wife Claudette in a 1966 motorcycle accident and two sons in a 1968 house fire, the song took on an even deeper weight whenever he performed it, including his 1987 duet with k.d. lang. What started with a chance meeting on a Texas street stayed at the center of his music for the rest of his life.

In 1958, Roy Orbison used what little money he had to buy out his contract at Sun Records, trading a label deal for the back seats of parked cars. After his 1956 single “Ooby Dooby” charted, Sun owner Sam Phillips pushed the shy, nearsighted singer in thick glasses to shout and gyrate like Elvis Presley or Jerry Lee Lewis. Refusing to spend his career faking wild rockabilly on stage, Orbison paid his way out of the contract and walked away broke. His young wife, Claudette, was expecting their first child, and relatives urged him to quit music for a steady paycheck in the West Texas oil fields where his father worked. Orbison had studied geology at North Texas State College with that very path in mind, yet he chose to keep driving overnight between Texas and Nashville’s Music Row to pitch songs for Acuff-Rose and send small checks home. With no money for motels, he slept in the back of friends’ cars or on the apartment floor of his songwriting partner, Joe Melson, before smoothing out his suit each morning to audition ballads that executives called too slow for radio. A brief deal at RCA Victor brought more commercial failures, until producer Chet Atkins realized RCA did not know how to use Orbison’s operatic voice and steered him toward Fred Foster at the new independent label Monument Records in 1959. Back home in Odessa, Texas, Orbison and Melson sat for hours inside a car parked at the curb, building orchestral ballads around his natural range. After Elvis Presley and the Everly Brothers both turned down their new song, “Only the Lonely,” Foster let Orbison record it his own way with strings in the spring of 1960. The record reached No. 2 in the United States and No. 1 in Britain, proving that the quiet Texan standing still behind the microphone never needed to imitate anyone else.

On February 22, 1968, Johnny Cash stopped his band in the middle of a song in London, Ontario, refusing to play on until June Carter agreed to marry him. Cash had been asking since they first met backstage at the Grand Ole Opry in 1956. Over the next twelve years, he proposed at least 30 times, and Carter always said no. When his addiction to pills and alcohol nearly killed him, Carter and her parents moved into his home, took away his drugs, and stayed up through the nights to watch over him, though she refused to become his wife until he got clean. By early 1968, Cash had turned his life around, recording his live album at Folsom Prison in January with Carter singing beside him. A month later in Canada, he carried a diamond ring in his suit pocket for days, waiting for a moment where she could not dodge the question or slip backstage. At the London Gardens arena, in front of 7,000 fans, he stopped their Grammy-winning duet “Jackson” and pulled out the ring. Carter had grown up performing with her family and knew how to handle any crowd, yet she blushed, clasped her hands together, and tugged at his coat sleeve, urging him to keep singing. Cash waited at the microphone while 7,000 people cheered for an answer. After she finally said yes, the two held hands backstage and decided to fly to the Bahamas the very next day. One week later, on March 1, 1968, they married at a church in Franklin, Kentucky. They stayed together on the road and at home for 35 years, until Carter passed away in May 2003 and Cash died four months later.

In 2003, Toby Keith stepped onto Willie Nelson’s tour bus in Las Vegas to celebrate their number one duet and ended up missing his flight the next morning. That week, “Beer for My Horses” was in the middle of a six-week run atop the Billboard Hot Country Songs chart. The two had gathered in Vegas for the Academy of Country Music Awards and a television special marking Nelson’s 70th birthday. After the show, Nelson invited his younger singing partner aboard his famed bus, Honeysuckle Rose. Standing over six feet tall, Keith carried the reputation of a burly Oklahoma powerhouse who could hold his own anywhere. He had actually quit smoking years earlier to keep up with his work schedule, yet nobody in country music said no when Willie Nelson offered to share on his own bus. It took very little to knock the younger star flat. Dizzy and overwhelmed, Keith made his way back to his room at the Mirage, slept for hours, and missed his plane the following day. Once he woke up aboard his own bus, Big Dog Daddy, he told the whole story to his longtime guitarist and co-writer Scotty Emerick. Laughing at the misadventure, the pair grabbed acoustic guitars and wrote “I’ll Never Smoke Weed with Willie Again.” Before releasing it, Keith played the demo for Nelson to make sure the joke landed right. Nelson laughed until tears came to his eyes and gave his full blessing. Keith included the recording as a hidden bonus track on his November 2003 album Shock’n Y’all, and fans requested it at his shows for the next twenty years. Even after Keith passed away in February 2024, that night in Vegas stayed with listeners as a favorite memory of a superstar who never minded making himself the punchline alongside his hero.

A week after September 11, Toby Keith wrote Courtesy of the Red, White and Blue in twenty minutes on the back of a fantasy football sheet. Six months earlier, in March 2001, his father, Hubert K. Covel Jr., died in a highway crash involving a bus with failed brakes. An Army veteran who lost an eye in service without ever complaining, Covel raised the American flag in his Oklahoma yard every morning. When the September 11 attacks occurred, Keith was still mourning that sudden loss and wondering how his father would have responded. At home with his guitar, Keith placed his father at the center of “Courtesy of the Red, White and Blue (The Angry American).” Initially, he refused to record it commercially, worried listeners would think he was profiting from his father’s death and national tragedy. He kept the song private, playing it acoustically only for young troops preparing to deploy. Late in 2001, Keith performed the song at the Pentagon and Marine Corps headquarters, where troops stood cheering in tears. Afterward, Marine Corps Commandant General James L. Jones put a hand on Keith’s shoulder and told him it was his civic duty to release the song for the nation. Keith released it in May 2002 as the lead single from his album Unleashed. The song hit No. 1 on the Billboard Hot Country Songs chart and entered the Billboard Hot 100 Top 25. Those early military performances also led Keith toward eleven USO tours to frontline bases in Afghanistan and Iraq. Written on scrap paper as a goodbye to one Oklahoma veteran, the song carried the memory of his father raising the morning flag to thousands of troops overseas.

Halfway through a 2014 concert on his Shut Up and Hold On Tour, Toby Keith stopped the music and invited a wounded combat veteran onto the main stage. Working with The Independence Fund, Keith surprised the soldier, who had lost both legs in service, with a $15,000 Action Trackchair in front of thousands of fans. Built with heavy treads instead of standard wheels, the chair was engineered to cross mud, sand, snow, and wooded trails where ordinary hospital wheelchairs could never roll. After handing over the keys, Keith leaned down to hug the veteran at eye level and stepped back from the microphone, asking the arena to stand and salute the man in the center of the stage. That night was not a single publicity stop. Through an ongoing partnership with The Independence Fund, Keith helped present tracked chairs to severely wounded veterans at multiple concerts across the country. That dedication came directly from the way he was raised. His father, Hubert K. Covel Jr., was a United States Army veteran who lost an eye during military service and died in a car accident in March 2001. Honoring his father’s memory, Keith spent years separating politics from the people in uniform, flying into remote bases on eleven USO tours to play for more than 250,000 troops in Iraq and Afghanistan. For the men and women who rolled off his stage in an Action Trackchair, the moment lasted far beyond a night of country music. Once they returned home, those treads meant a husband or father could head back into the woods, reach the edge of a fishing lake, or take his kids across a park without waiting for someone else to push.

In 1999, Nashville executives told Toby Keith that his new music had no commercial future, so he used his own money to buy back the album and walk away. At the end of the 1990s, Mercury Records wanted polished pop country built for easy radio play. Keith, a former Oklahoma oil field hand, had gone into the studio with something much louder. Working with songwriter Chuck Cannon, he had written a defiant track titled “How Do You Like Me Now?!” and built an entire album around that unapologetic sound. When he played the finished tapes for the label brass, the executives turned the project down flat, arguing the lead song was too brash to sell. Rather than letting the music sit on a shelf or softening his style to protect a major contract, Keith bet on himself. He used his own savings to purchase the master recordings from Mercury and walked out a free agent. Carrying an album that his old label had just written off, he met with producer James Stroud at the newly launched DreamWorks Records Nashville. Stroud believed in the recordings immediately and signed Keith, agreeing to release the project without changing a single note. Sent to radio in late 1999, “How Do You Like Me Now?!” caught fire with listeners from small town bars to highway pickup trucks. The single climbed to No. 1 on the Billboard Hot Country Songs chart, held the top spot for five straight weeks, and finished 2000 as the biggest country song of the entire year. A track written about proving doubters wrong ended up doing the exact same thing for the man singing it. By putting his own money on the line for those master tapes, Keith launched the defining decade of his career on his own terms.

At a remote desert outpost with no stage or sound system, young soldiers planted spent mortar shells in the sand to build Toby Keith a place to sing. Across eleven USO tours in Iraq and Afghanistan, Keith performed for more than 250,000 American service members. While many entertainers stayed at larger rear bases with full production crews, he repeatedly boarded military helicopters to reach small forward operating bases near the front lines. Many of those outposts had nothing ready for a visiting musician. At one desert camp, troops gathered empty mortar casings still darkened by powder and set them upright in the dirt. Inside the scorched metal tubes, they wedged flashlights aimed toward the night sky, turning a patch of dry ground into a makeshift amphitheater. Keith stepped into that circle of light with just an acoustic guitar. No security barriers stood between the performer and the unit. Sitting on an ammunition crate as red desert dust coated his boots and the neck of his guitar, he sang for troops who were mostly in their early twenties. As the evening went on, the yellow beams from the shell casings lit up dusty uniforms and quiet, homesick faces gathered shoulder to shoulder. Keith stayed right there with them, sharing water and trading stories about home in the calm between patrols. Packed arenas and radio hits built his career in the States. Still, year after year, Keith returned to the places where an acoustic guitar and a row of flashlights in empty shells meant a piece of home had found its way to the front lines.

When a July 2022 cycling accident left Amy Grant unable to recall songs she had sung for forty years, Vince Gill cleared his schedule to help her start over. The fall happened on July 27 at Nashville’s Percy Warner Park after her bicycle wheel hit a pothole, leaving her unconscious for ten minutes despite her helmet. She spent two nights at Vanderbilt University Medical Center with a traumatic brain injury, just two years after undergoing open-heart surgery in June 2020 for a congenital defect. Back home, the lingering effects of the concussion took hold. Sensitivity to light and noise kept her in a quiet room with the curtains drawn, while balance issues forced an avid walker to move one slow step at a time. Worse still, short-term memory loss erased family stories, the names of longtime colleagues, and the words to songs from her four-decade career. Vince immediately postponed her fall tour and canceled his own upcoming performances, turning off electronics and limiting visitors at their Nashville house. Every afternoon, he walked beside her with an arm around her waist to steady her down the hallway and along the garden path. When she cried in the dark and asked if this was all she had left, he held her and promised to do the remembering for her while she began writing daily notes in a journal. By November and December 2022, she was ready to attend the Kennedy Center Honors and join him for their annual Christmas at the Ryman residency. Vince placed large notebooks and a teleprompter in front of her onstage, staying close enough to rest a hand on her shoulder and cover any brief pause with gentle humor until she found her next line.