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Greatest Hits Oldies But Goodies Ever

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.

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Writing a check for roughly $93,000 in 1999 allowed Toby Keith to buy back his own rejected recordings from Mercury Nashville and carry them straight to DreamWorks Records.

Before that standoff, the former Oklahoma oil field hand had spent six years under the PolyGram corporate umbrella, getting shuffled from Mercury to Polydor, over to A&M, and finally back to Mercury. Although his 1993 debut single “Should’ve Been a Cowboy” became the most-played country song of the decade, label executives still treated him like a secondary act as late-1990s radio leaned heavily toward polished pop crossovers.

Working alongside producer James Stroud and songwriter Chuck Cannon, Keith recorded a batch of rowdy, horn-driven tracks anchored by a defiant new song called “How Do You Like Me Now?!”. When he delivered thirteen finished tracks to Mercury Nashville chairman Luke Lewis, the label rejected nearly the entire project, pulling only two songs to package onto his 1998 Greatest Hits Volume One compilation.

Keith tried cutting two more songs to satisfy the front office, and Mercury turned those down as well. Sitting down with Lewis, Keith told the executive man-to-man that they did not see eye to eye and asked to be released from his contract so he could provide for his family.

Rather than leaving his unreleased sessions locked in a corporate vault, Keith negotiated to purchase the master tapes himself for just under $100,000. He walked out a free agent holding a completed album that his longtime label believed had no commercial future.

Across town, Stroud had recently taken over as head of the newly launched DreamWorks Records Nashville. Having co-produced the sessions, Stroud knew what was on those reels and signed Keith immediately, paying $200,000 for the masters and releasing the album on November 2, 1999, without altering a note.

Sent to country radio as the title track, “How Do You Like Me Now?!” climbed to No. 1 on the Billboard Hot Country Songs chart, stayed on top for five consecutive weeks, and crossed over into the Top 40 on the all-genre Billboard Hot 100. The song finished 2000 as the number one country single of the year, while the follow-up ballad “You Shouldn’t Kiss Me Like This” added another three weeks at the summit and pushed the album past triple-platinum sales.

At the Academy of Country Music Awards in May 2001, Keith stepped to the microphone to accept both Top Male Vocalist and Album of the Year for the very recordings Mercury had refused to release. Holding the trophies, he told the crowd he had waited nine years for that recognition.

That breakthrough ignited a five-album run at DreamWorks that turned Keith into country music’s dominant commercial force of the early 2000s. His 2001 follow-up, Pull My Chain, debuted at No. 1 and delivered three consecutive chart-toppers with “I’m Just Talkin’ About Tonight,” “I Wanna Talk About Me,” and “My List.”

He followed with Unleashed in 2002 and Shock’n Y’all in 2003, a pair of multi-platinum blockbusters that sold more than four million copies apiece and produced staples including “Courtesy of the Red, White and Blue (The Angry American),” “Who’s Your Daddy?,” “Beer for My Horses” with Willie Nelson, and “I Love This Bar.”

In an ironic corporate twist in 2004, Universal Music Group acquired DreamWorks Records and folded its Nashville roster back under Luke Lewis’s oversight. Keith completed one final album under the banner, 2005’s Honkytonk University, which gave him a six-week No. 1 hit with “As Good as I Once Was.”

Months later, when DreamWorks Nashville shut its doors in August 2005, Keith used the leverage and fortune built over those six years to launch his own independent label, Show Dog Nashville, ensuring he would never again have to ask an executive for permission to release his own music.

A check for $93,000 in 1999 did more than rescue a rejected tape from a Music Row shelf. It handed Toby Keith the keys to his own career and proved that the songs he believed in were worth every dollar he put on the line.

https://www.youtube.com/watch?v=3umaLe37-LE&list=RD3umaLe37-LE&start_radio=1

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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.

In 1975, while country radio was filled with songs about barroom infidelity and broken marriages, Don Reid wrote a ballad about keeping a wedding vow until the end of life. Released as a single from The Statler Brothers’ album The Holy Bible: Old Testament, “I’ll Go to My Grave Loving You” climbed to number three on the Billboard Hot Country Singles chart and became one of the quartet’s biggest records of the 1970s. Don drew the song from his own marriage to his high school sweetheart, Brenda, back home in Staunton, Virginia. With his older brother Harold anchoring the bass and Phil Balsley and Lew DeWitt completing the four-part harmony, the record sounded less like a stage performance and more like a quiet promise made in a living room. Eighteen years later, the brothers returned to that same theme from the other side of middle age. By 1993, as the group members entered their fifties and sixties, Don and Harold Reid sat down together to write “I’ve Never Lived This Long Before” for their album Home. Backed by Phil Balsley and tenor Jimmy Fortune over a sparse, unhurried arrangement, the two men traded their usual stage humor for an honest look at graying hair and the quiet surprise of growing old. Where the 1975 hit carried the steady voice of a young husband looking ahead, the 1993 recording sounded like two longtime partners talking across the dinner table after decades together. Rather than chasing a younger crowd in the 1990s, The Statler Brothers chose to age right alongside the people who bought their records. Those two songs, recorded eighteen years apart, went on to be played at countless silver and golden wedding anniversaries and funeral services across America, giving couples the words for both the promise of youth and the gratitude of old age.

Long before Conway Twitty earned 40 number one singles on the Billboard country charts, an elderly Black neighbor in the Mississippi Delta taught a six-year-old white boy how to play the blues on a cheap Sears & Roebuck toy guitar. Born Harold Lloyd Jenkins on September 1, 1933, he grew up during the Great Depression in Friars Point, Mississippi. His parents, Mississippi River ferryboat captain Floyd Jenkins and his wife Velma, raised their family among one of the few white households in a community of Black cotton pickers and sharecroppers. When Harold’s grandfather, Papaw McGinnis, ordered him a mail-order guitar with stiff steel strings around age four or five, the boy took it next door to an older neighbor he respectfully called Uncle Fred. After long days working in the cotton fields, Uncle Fred sat on his wooden porch with an old guitar and a harmonica, showing the boy how to press the strings without hurting his fingers and how to slide a glass bottleneck or pocketknife blade along the neck. Even under the strict racial segregation of the Jim Crow South in the late 1930s, Floyd and Velma Jenkins encouraged their son to learn from Uncle Fred and treat him like family. On Sunday nights, the Jenkins family stood outside the open windows of the local Black church to listen to the gospel choir, while young Harold also absorbed the rhythms drifting from nearby juke joints. When the family moved across the river to Helena, Arkansas, in 1943, the ten-year-old carried those Delta blues and gospel lessons into his first band, the Phillips County Ramblers. Decades later, whenever interviewers asked where he found the low vocal growl and phrasing that carried him from 1950s rockabilly to the top of country radio, Twitty pointed back to Uncle Fred on that wooden porch in Friars Point.

On October 12, 1991, over 2.2 million American households tuned in at 9 p.m. to watch four men in tailored suits sing gospel and country harmonies, breaking the all-time premiere record for The Nashville Network. By the early 1990s, commercial country music was rapidly chasing younger crowds with pyrotechnics and arena rock production. Harold Reid, Don Reid, Phil Balsley, and Jimmy Fortune went the opposite direction. Stepping onto the stage just over a year after losing founding tenor Lew DeWitt in August 1990, the quartet built The Statler Brothers Show around the classic variety format they grew up loving. For seven seasons and more than 150 episodes, the formula never changed. The four men stood close together at the microphones, traded clean Vaudeville-style comedy sketches featuring Harold as Lester “Roadhog” Moran, and closed every single Saturday night broadcast with a solemn gospel hymn. Three generations of families could sit in the same living room without ever reaching for the remote. While mainstream country radio was quietly pushing older pioneers off the airwaves, the Statlers used their top-rated stage to welcome them home. They gave a place of honor in their first season to Johnny Cash, the mentor who had carried them on tour for over eight years early in their career, and regularly hosted veterans like Loretta Lynn, George Jones, Conway Twitty, and Roy Rogers. The show remained the number-one program on the entire network until its final broadcast in May 1998, ending only because new corporate owners wanted a younger demographic. After each taping in Nashville, all four men still packed their bags and drove straight back to their families and local churches in Staunton, Virginia, leaving behind a seven-year television run that proved old-fashioned grace never actually lost its audience.

In February 1979, five years after Dolly Parton wrote “I Will Always Love You” to say goodbye to Porter Wagoner, her former mentor sued her for $3 million, and years later she still stepped in to save him from losing everything. When Parton left The Porter Wagoner Show in 1974, their careers moved in opposite directions. She crossed into pop music with her 1977 hit “Here You Come Again,” won the 1978 CMA Entertainer of the Year award, and prepared to film “9 to 5” in Hollywood, while Wagoner faced stalling sales and financial trouble. In his 1979 federal lawsuit in Nashville, Wagoner demanded 15 percent of Parton’s future earnings and claimed co-ownership of Owe-Par, the publishing company she had founded at age 21 with her uncle Bill Owens to protect the hundreds of songs she wrote between 1967 and 1974. While smiling on the “9 to 5” film set by day, Parton spent months dealing through lawyers with the man who had once defended her against booing audiences in 1967. In 1980, she agreed to pay Wagoner $1 million in installments out of her studio, touring, and film income to settle the suit and keep full ownership of her songwriting catalog. Seven years later, Parton ended the silence by inviting Wagoner onto her 1987 television show, where they embraced on stage. When severe IRS debt threatened to wipe Wagoner out in the late 1980s, Parton bought the rights to their shared duet catalog to help him clear his debts, then returned those rights to him once he recovered financially. In 2007, Parton sat by Wagoner’s hospital bed and held his hand shortly before he passed away, having long since forgiven the lawsuit between two proud partners who had shaped each other’s lives.

In February 2021, Tennessee lawmakers from both political parties united to place a statue of Dolly Parton on the State Capitol grounds, and she wrote a letter asking them to stop. Weeks earlier, State Representative John Mark Windle had introduced House Bill 0136 to honor Parton in Nashville for everything she had given the state. Even though the monument would be funded through private donations rather than taxpayer money, the bill was moving easily toward approval when Parton stepped in on February 18, 2021. Given everything the world was enduring during the height of the COVID-19 pandemic, she told the legislature that she did not think putting her on a pedestal was appropriate at that time. While thousands of families were grieving and struggling to buy food and medicine, she did not want private funds or public attention spent casting her likeness in metal. Months before turning down the monument, Parton had donated $1 million to Vanderbilt University Medical Center in Nashville to help fund early research for the Moderna COVID-19 vaccine. The gift grew out of her friendship with Dr. Naji Abumrad, who had treated her after a minor 2013 car accident, and Parton was surprised when her name later appeared in the New England Journal of Medicine. She always cherished the modest 1987 bronze statue on the courthouse lawn in her hometown of Sevierville, yet she repeatedly stepped back from grander honors, twice declining the Presidential Medal of Freedom while her husband was ill and initially asking to withdraw from the 2022 Rock & Roll Hall of Fame ballot. To soften the refusal for Nashville lawmakers, Parton ended her 2021 letter by joking that if they still felt she deserved a Capitol statue several years down the road or after she was gone, she would proudly stand there as a grateful Tennessee citizen.

On August 26, 2026, the clock tower at the Sevier County Courthouse rang for five straight minutes to say goodbye to a local farmer’s daughter who once walked past those steps barefoot. One day after Dolly Parton’s passing, Sevier County officials held an official hometown memorial in the center of Sevierville, Tennessee. As the historic bells echoed toward the Great Smoky Mountains, thousands of residents, visitors, and county leaders gathered on the courthouse lawn. When the final chime faded, the entire town entered five minutes of silence. Along the Parkway and the streets surrounding the square, drivers pulled over, turned off their engines, and stepped out with their hats in their hands. Nearby shopkeepers paused their work and stood in the doorways. The crowd gathered around the bronze statue of a young Dolly holding a guitar, sculpted by Jim Gray and placed on the lawn in May 1987. Parton often said that hometown tribute meant more to her than any Grammy or Hollywood award, and she loved telling how her father, Lee Parton, used to sneak out at night with a bucket of soapy water and a broom to scrub bird droppings off the bronze himself. In the 1950s, the fourth child of Lee and Avie Lee Parton rode into town from Locust Ridge in a worn-out truck, wearing patched clothes past that same courthouse. Decades later, her Dollywood park, Buddy Program scholarships, hospital funding, wildfire relief, and Imagination Library had created tens of thousands of jobs and supported generations across East Tennessee. At the base of the stone pedestal, former 1964 Sevier County High School classmates and young children who grew up receiving her monthly books left mountain wildflowers, small guitars, paper butterflies, and children’s storybooks on the grass where her father once stood with his bucket and broom.

For seven years, audiences watching Dolly Parton and Porter Wagoner sing together were convinced they were secret lovers, while her husband Carl Dean quietly trusted her from their Nashville farm. When Dolly joined The Porter Wagoner Show in September 1967 at age 21, Porter was separated from his second wife, Ruth Olive Williams, and newly split from former singing partner Norma Jean. Dolly had been married for over a year to Carl Dean, an asphalt paving businessman she wed on May 30, 1966, in Ringgold, Georgia. After attending one BMI awards dinner in a tuxedo in 1966, Carl told Dolly he loved her rather than her industry and stayed home, never letting gossip cross their threshold. Between 1967 and 1974, Porter and Dolly recorded 13 studio albums together and won CMA Vocal Duo of the Year in 1968, 1970, and 1971. The way they held hands and looked at each other during songs like “Holding On to Nothin’,” “Just Someone I Used to Know,” and “Please Don’t Stop Loving Me” left millions of viewers and Nashville reporters certain they were hiding a romance. Both maintained their bond was never physical. Behind the curtain, Dolly was one of the few people willing to argue with Porter over every note and arrangement, and that stubborn friction gave their stage performances an unusual charge. On the Wagon Masters tour bus, she kept clear boundaries, spending her spare hours writing songs alone or calling Carl. Porter later admitted that he loved Dolly deeply, mixing a mentor’s pride with the bond of seven years side by side, though he knew her heart belonged to her husband and her own music. In October 2007, long after their 1970s legal battles had faded and hours before Porter died of lung cancer at age 80, Dolly stood by his hospital bed, held his hand, and softly sang to him one last time.