OldiesSong

Greatest Hits Oldies But Goodies Ever

During his final road concert at Milwaukee’s Fiserv Forum on May 17, 2025, Alan Jackson stepped back from the microphone near the end of “It’s Five O’Clock Somewhere” and stopped singing. As he fell quiet, Jimmy Buffett’s original recorded vocal echoed across the 17,000-seat arena for the song’s closing part. Behind Jackson, the giant LED screen lit up with a photo of a barefoot Buffett smiling out on the open water. Back in the summer of 2003, Jackson had nearly passed on recording the carefree duet unless Buffett agreed to sing on it with him. Once together, they carried the track to eight straight weeks at number one on the Billboard country chart and won the CMA Award for Vocal Event of the Year, handing Buffett his very first CMA trophy after decades of making music. Away from studios and arenas, the two spent more than twenty years as close friends, trading fame for boats, fishing rods, and quiet afternoons off the Florida coast. Everything about playing that lighthearted summer anthem changed after September 1, 2023, when Buffett passed away at age 76 following a quiet four-year fight with Merkel cell skin cancer. Throughout the 2024 and 2025 stretch of his farewell tour, Jackson kept a permanent spot in the setlist for his late friend. On that final night in Milwaukee, Jackson leaned against his microphone stand to steady legs weakened by incurable nerve disease, turned toward the sunlit portrait overhead, and raised his white cowboy hat toward the rafters. Across the arena floor, thousands of fans lifted their cups to the screen as Jackson made sure his old fishing partner shared the stage on the last road show of his life.

Please scroll down for the video. It is at the end of the article!

ALAN JACKSON STEPPED BACK FROM HIS MICROPHONE ON HIS FINAL ROAD SHOW SO JIMMY BUFFETT COULD FINISH THEIR SONG ONE MORE TIME.

On Saturday night, May 17, 2025, Alan Jackson walked onto the stage at Milwaukee’s Fiserv Forum for the closing stop of his Last Call: One More for the Road Tour. Before a sold-out crowd of roughly 17,000 fans, the 66-year-old Georgia traditionalist confirmed that the Wisconsin arena date marked the final road concert of a touring life stretching back nearly four decades.

Near the end of the set, Jackson and his longtime band, The Strayhorns, kicked into the breezy summer rhythm of “It’s Five O’Clock Somewhere”. Instead of singing through the closing section himself, Jackson stepped back from his microphone and let the arena go quiet at center stage.

Seconds later, Jimmy Buffett’s original recorded vocal rolled out over the speakers to carry the song’s final stretch. Above the band, the giant LED screen lit up with a sunlit photograph of a barefoot Buffett smiling out on the open water.

That shared coastal world began in the spring of 2003, while Jackson was pulling together two new tracks for his *Greatest Hits Volume II* collection. Songwriters Jim “Moose” Brown and Don Rollins had crafted the lighthearted escapist tune about ducking out of work early to unwind by the water—built deliberately around a laid-back Gulf Coast groove after Kenny Chesney originally passed on cutting it.

Jackson liked the demo right away, though he hesitated to record a tropical barroom song unless Buffett himself agreed to jump in on the final chorus and trade banter at the end. Working through mutual connections, Jackson sent the rough track south, and Buffett tracked his vocal part in a Florida studio while keeping his guest appearance an unannounced surprise until the single hit country radio on June 2, 2003.

Weeks later, director Trey Fanjoy filmed the pair side by side at the Square Grouper Tiki Bar on the Jupiter Inlet in Florida, just down the coast from one of Jackson’s homes, with Jackson’s own classic wooden boat, *Hullbilly*, moored nearby. Released that summer, the duet spent eight consecutive weeks at number one on Billboard’s country chart, climbed to number seventeen on the all-genre Hot 100, and won the 2003 CMA Award for Vocal Event of the Year—handing Buffett the very first CMA trophy of his storied career.

What started as a studio pairing quickly settled into more than twenty years of easy friendship away from Nashville business. Sharing neighbors’ stretches of the South Florida shoreline around Jupiter and Palm Beach, the tall Georgia country singer and the Gulf Coast troubadour traded tour buses for salt water, boats, and quiet afternoons with fishing rods.

They carried that camaraderie back into the studio in 2004 for Buffett’s chart-topping album *License to Chill*, singing together on Guy Clark and Verlon Thompson’s “Boats to Build” alongside a multi-artist romp through Hank Williams’s “Hey Good Lookin'” before sharing stadium bills with George Strait at Texas Stadium.

Every carefree note of their signature hit took on a different weight after September 1, 2023, when Buffett passed away peacefully at age 76 following a private four-year illness with Merkel cell skin cancer. Jackson mourned his friend publicly by recalling their song about building boats and sailing toward distant shores, then joined Chesney, Mac McAnally, and Zac Brown Band at Nashville’s Bridgestone Arena that November to salute him at the 2023 CMA Awards.

When Jackson returned to arenas across 2024 and 2025 to finish his own farewell run while managing Charcot-Marie-Tooth nerve disease, he kept his old friend’s voice untouched in the nightly setlist.

In Milwaukee, keeping one steady hand near his microphone stand to balance weakened legs, Jackson turned his back to the crowd to look up at the barefoot singer smiling across the screen. As Buffett’s recorded voice wrapped up the final lines, Jackson lifted his white cowboy hat high toward the rafters while thousands of fans raised plastic beer cups toward the portrait overhead.

One hometown stadium bow in Nashville still waited the following summer, yet Alan Jackson refused to close his years on the highway without leaving five minutes open for his old Florida fishing partner.

https://www.youtube.com/watch?v=BPCjC543llU

Related Post

In their final years together, Johnny Cash and Waylon Jennings stopped talking much about records or road stories and started checking on each other’s blood sugar, joint pain, and medication schedules. Their brotherhood began back in a shared 1960s Nashville apartment, long before outlaw country made either of them a household name. Two restless young men split cheap meals, shared living space, and pulled each other through addiction and personal crises until both found family peace. Decades later, they stood side by side again in The Highwaymen alongside Willie Nelson and Kris Kristofferson, carrying that real-life loyalty onto stages around the world. By the late 1990s and early 2000s, time had given them a much harder road to walk together. Both men were battling advanced diabetes, severe peripheral nerve damage, failing eyesight, and declining mobility. Backstage and on front steps, the once-defiant cowboys took hold of each other’s hands to climb stairs one careful step at a time. During their last performances together, fans saw two weathered friends look across the stage with quiet gratitude simply to still be standing side by side. When Waylon died in Arizona in February 2002 at age 64, the loss hit Johnny at a moment when his own body was already failing fast. Frail and exhausted, Cash still gathered the strength to pay tribute to the man he considered a brother, keeping faith to the end with the old roommate who had steadied his steps from a cramped Nashville apartment to their last stairs backstage.

In March 1991, as 87-year-old Carrie Rivers Cash neared the end of her life in a hospital room, Johnny Cash reached for an acoustic guitar. Long before the world knew his voice, his mother had heard it first on the poor cotton fields of Dyess, Arkansas, during the Great Depression. While stooping down the rows in the heat with calloused hands, she sang church hymns to ease the labor and taught young Johnny to sing beside her. Money barely existed in that home, yet Carrie still scraped together the spare coins earned from selling a calfskin to pay for her son’s very first formal singing lessons. Johnny never forgot what those early lessons cost her. When her final hours arrived decades later, he gathered constantly around her hospital bed alongside his wife, June Carter Cash, and generations of children and grandchildren. Refusing to let fear or heavy silence take over the room, Johnny began strumming his guitar. June joined him in harmony, bringing her own family’s lifelong tradition of group singing to his mother’s bedside as the rest of the family lifted their voices together. One after another, they filled that sterile hospital room with the familiar childhood hymns Carrie had carried across the Arkansas dirt so many years earlier. Surrounded by her family’s voices, Carrie passed away peacefully inside the exact music she had first given her son, sent home by the boy whose singing started with her calfskin money.

At Oakwood Cemetery Annex on Upper Wetumpka Road in Montgomery, Alabama, the graves of Hank Williams and his first wife, Audrey Mae Sheppard, sit surrounded by bright green artificial turf because visiting fans once plucked every blade of real grass as a keepsake faster than it could grow back. Married at an Andalusia gas station in 1944, the couple shared one of country music’s stormiest bonds. Audrey acted as his first manager, pushing him toward Nashville, while their bitter fights and heartbreak fueled many of his most enduring songs. On New Year’s Eve 1951, as Hank’s drinking and deep marital rifts pushed them toward a June 1952 divorce, he told Audrey he would not live another year without her. Early on New Year’s Day, January 1, 1953, the 29-year-old singer passed away in the backseat of his pale blue Cadillac after briefly remarrying Billie Jean Jones. Three days later, following a service that drew more than 20,000 mourners around Montgomery Municipal Auditorium in one of the largest funerals in Alabama history, he was laid to rest at Oakwood Annex. Audrey never remarried. She paid Billie Jean $30,000 to claim sole legal use of the title of Hank Williams’ widow and spent her remaining 22 years surrounded by his keepsakes in their old Nashville home. When heart failure claimed her life on November 4, 1975, at age 52, she was brought back to Montgomery and buried directly beside her former husband. Today, two tall white marble monuments stand side by side just a mile from the museum housing his final Cadillac, with Hank’s stone bearing musical notes, a guitar, his “Luke the Drifter” alias, a carved marble cowboy hat, and Audrey’s own tribute lines. Each January 1 and September 17, visitors from across the South and as far as England and Japan still gather on that green turf to touch the stone hat, where two people who could find no peace together in life finally rest side by side.

Even as Alabama stacked dozens of consecutive No. 1 hits and passed 73 million records sold, Randy Owen and his wife, Kelly, refused to move to Nashville or Los Angeles. They stayed in Fort Payne, Alabama, honoring a choice rooted in 1975, when they married while Randy was still singing for spare change in glass tip jars along Myrtle Beach bars. Raised in a poor cotton-sharecropping family, Randy had watched his father wear himself out on rocky fields. Once music money arrived, he and Kelly bought thousands of acres atop Lookout Mountain, the same ground his father and grandfather once worked for others, and built Tenbroeck Hereford Farm into a respected Southern purebred Hereford and Angus cattle operation. Whenever the tour bus dropped him off from sold-out arenas, Randy traded stage clothes for muddy rubber boots and drove a tractor out at dawn to check his herd. While he spent hundreds of nights a year on the road, Kelly kept the cattle books and guarded quiet family dinners from media noise. Their children, Alison, Heath, and Randa, skipped red carpets and celebrity private schools. Instead, they fed cattle, baled hay, mended wooden fences, and showed livestock at local fairs without millionaire privileges. Around town, neighbors still found Randy in a worn shirt and old cap drinking morning coffee at a roadside diner or talking pasture grass. Through the band’s annual June Jam throughout the 1980s and 1990s, Randy also brought tens of thousands of fans to Fort Payne, raising millions for local schools, hospitals, and neighbors. Nearly half a century of farm work beside Kelly later steadied him through prostate cancer treatment in 2010, keeping him grounded right on the mountain ridge his family once farmed for someone else.

On November 11, 2020, 86-year-old Charley Pride stepped onto the CMA Awards stage to accept the Willie Nelson Lifetime Achievement Award and thank his wife in the front row. Rozene Cohran was working as a cosmetologist in Memphis when she met Charley, then a broke Negro League baseball player from the cotton fields of Sledge, Mississippi. They married on December 28, 1956, during a brief Army leave. By the early 1960s in Montana, Charley worked days at a smelter, played semipro ball, and sang in small clubs at night while Rozene raised their children, Kraig, Dion, and Angela. When RCA signed him in 1966, executives left his face off early single releases, worried Southern radio would reject a Black country singer. Rozene steadied him through that isolation and took charge of their finances and contracts so the industry could not exploit him like so many Black artists of that era. In 1969, they settled in Dallas instead of Nashville to give their family a quiet, safe home life. Behind closed doors, Rozene also stayed beside Charley through decades of bipolar disorder when stage applause offered no relief. He became the first Black superstar inducted into the Country Music Hall of Fame, always saying half of every platinum plaque on his wall belonged to her. One month after looking down from that Nashville podium to credit her for keeping his life and career intact, Charley entered a Dallas hospital with severe COVID-19 complications under strict pandemic isolation rules. He passed away on December 12, 2020, sixteen days shy of their sixty-fourth wedding anniversary, leaving his last public words right where his whole journey began, with Rozene.

On March 1, 2016, at age 76, Don Williams quietly stepped away from a 56-year music career with a brief statement saying it was time to hang up his hat and rest. A month earlier, in early February 2016, the singer known around the world as the Gentle Giant had canceled a spring tour of more than 20 cities for emergency hip replacement surgery. Emphysema was also steadily draining his breath and stamina. Williams had tried retiring once in 2006 before returning to the road in 2010, the same year he entered the Country Music Hall of Fame, and his shows still sold out across North America, the United Kingdom, Ireland, and African nations like Kenya and Zimbabwe following his 2014 album Reflections. This time, feeling his strength fade, he skipped a big farewell tour and went straight home to Joy Janene Bucher, the wife he married in April 1960, and their sons Gary and Timmy. Before Nashville knew his warm baritone, Joy had stood beside him through lean early-1960s years in Texas while he drove delivery trucks, worked oil fields, collected bills, and sold furniture to feed their young family. Even after fame arrived, she stayed away from red carpets and press interviews, keeping their home steady through decades of overseas tours. Just as Williams spent his stage career sitting calmly on a high stool with an acoustic guitar and a worn cowboy hat, he left the spotlight without fanfare or self-pity. Walking away that spring gave them 18 uninterrupted months together, free of tour buses and airport schedules, before Williams passed away from emphysema in Mobile, Alabama, on September 8, 2017, at age 78. Having hung up his hat when it counted most, he spent every last morning and evening beside the woman who had waited for him across 57 years of marriage.

When Dolly Parton cashed the major royalty checks from her 1974 solo breakthrough, she headed home to Tennessee to buy her parents a sturdy brick house and a brand-new car. The fourth of twelve children in Sevier County’s Smoky Mountains, Dolly grew up in one- and two-room wooden cabins without electricity, running water, or an indoor bathroom. Three or four kids shared straw mattresses while winter snow blew through gaps in the boards onto their patchwork quilts. Watching her father work tobacco fields as a sharecropper and her mother stretch thin vegetable soup, young Dolly promised that her first music money would buy them a proper home. That chance arrived after she left Porter Wagoner’s television show and released I Will Always Love You, which reached No. 1 on the country chart in June 1974 while she kept full publishing rights. Soon after, Colonel Tom Parker wanted Elvis Presley to record the song if Dolly gave up half the publishing. She cried all night over losing Elvis’s version, then refused so those royalties could protect her family long term, a choice that earned millions in the 1990s. Nestled among familiar Sevierville pines, the new house gave Avie Lee, who once sewed Dolly a coat from scraps and hauled cold well water, a warm kitchen with hot running water. Robert Lee, a quiet laborer who could neither read nor write, held keys to property he never dreamed of owning. Refusing household help, her parents still woke before dawn to tend a small vegetable garden out back. Dolly also restored their childhood cabin and covered their medical and living needs until Robert died in 2000 and Avie followed in 2003, always calling the day they crossed that front threshold her sweetest achievement.

Between 1960 and 1975, as Kenny Rogers became a familiar face on television screens across America, he visited his firstborn daughter in Texas only once. In 1958, Rogers was a broke 19-year-old singer raised in Houston public housing by an alcoholic father. That year, he married his girlfriend Janice Gordon, and their daughter, Carole Lynne Rogers, arrived in September. Janice’s parents had better financial means and strongly opposed the match, convinced a struggling musician could never offer a stable home. When the marriage ended in April 1960, Rogers carried a deep shame over how little he had. Believing his daughter would have a safer future without him, he stepped aside in the divorce arrangement so Janice’s new husband could legally adopt her. Leaving Houston behind, he threw himself into years of relentless touring with The Bobby Doyle Three, The New Christy Minstrels, and later The First Edition. Back in Texas, Carole Lynne grew up able to watch her biological father sing on black-and-white television while remaining a stranger to him in real life. Their lone visit across those 15 years felt stiff and distant, with the little girl he once held having no memory of him. In his 2012 memoir, Luck or Something Like It, Rogers made no excuses for that absence, writing frankly that youth, selfishness, and musical ambition had overtaken his duty as a parent. When Carole Lynne reached her teens and adulthood, she chose forgiveness over resentment, allowing the two to slowly rebuild a warm bond across the second half of his life. Still, the 15 years missing from his eldest daughter’s childhood stayed on his conscience, later driving his decision in old age to leave the stage behind and stay home every day with his youngest twin sons.

Before Nashville ever heard his name, Alan Jackson spent more than a decade clocking into Georgia warehouses, carpentry shops, and basement mailrooms just to pay the bills. Right after graduating from Newnan High School in 1976 with no financial cushion or plans for stardom, he went straight into manual labor. Through the late 1970s and early 1980s, Jackson sold shoes, turned wrenches in greasy local garages, built household cabinets, worked construction, and drove a forklift for long shifts inside a windowless Kmart distribution warehouse in Newnan, humming quiet melodies over the engine noise. When he married his high school sweetheart, Denise, in late 1979 at age twenty-one, keeping up with rent and utility bills came first. Alan took whatever steady blue-collar paycheck he could find and saved his guitar playing at small local spots for rare weekend breaks. Denise, working as a flight attendant, never complained about his modest wages. Even when the couple took a gamble and moved to Nashville in 1985 at age twenty-seven with nothing in hand, Alan survived by sorting mail and hauling packages in the basement of The Nashville Network. Pushing a mail cart down those hallways, the tall young man in a hat stepped aside daily as famous stars walked into the studios without noticing him. Those years stayed with him once his records finally broke through. Standing calm behind the microphone in worn jeans and scuffed boots he had worn since cutting lumber in Georgia, his calloused hands held the guitar without flashy stage moves. Blue-collar Americans heard one of their own in his songs about working people, written by a man who still knew Friday exhaustion, weekly paychecks, sawdust, and motor oil firsthand.