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Greatest Hits Oldies But Goodies Ever

On March 15, 2008, Carrie Underwood finished singing a Randy Travis classic at the Grand Ole Opry without knowing the man who wrote it was waiting in the wings. Growing up in Checotah, Oklahoma, Carrie had listened to Randy’s cassette tapes in the family car. In 2007, she recorded his 1988 number one song, “I Told You So,” for her second album, Carnival Ride. When the 25-year-old stepped onto the Opry stage that March evening, she had no idea Randy was listening backstage. She later admitted she would have been too nervous to get through the song if she had known he was there. As the last note faded, Randy walked out onto the stage. Instead of simply congratulating her, he asked Carrie if she would become the newest member of the Grand Ole Opry. She covered her face with both hands, crying on live radio before she could steady herself enough to nod and hug him inside the wooden circle. Coming three years after her American Idol win, that endorsement from a traditional country giant quieted any lingering doubts in Nashville. Two months later, on May 10, 2008, fellow Oklahoma native Garth Brooks officially inducted her. Thirteen years earlier, a 12-year-old Carrie had waited after a concert to tell Garth she wanted to be a singer, and he had advised her to finish school first before they met again. In 2009, Randy joined Carrie for a duet recording of “I Told You So” that won a Grammy the following year. After a severe stroke in 2013 took away Randy’s singing voice, Carrie stayed close to the mentor who had welcomed her into the Opry family. At his 2016 Country Music Hall of Fame induction, she stood at the microphone and sang his classic back to him while he smiled from the front row.

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When Carrie Underwood walked down from the Grand Ole Opry stage on March 19, 2025, during the show’s centennial broadcast and held her microphone out to Randy Travis in the front row, seventeen years of shared history sat behind the single word he sang into it.

Their connection began long before they ever shared a stage, back when a young Underwood rode in her family’s car around Checotah, Oklahoma, listening to Travis’s cassette tapes. In 2007, two years after winning the fourth season of *American Idol*, she recorded his self-penned 1988 chart-topper “I Told You So” for her second studio album, *Carnival Ride*.

On March 15, 2008, the 25-year-old singer performed that cover at the Grand Ole Opry without knowing Travis was standing behind the curtain. After she finished the last note, Travis walked out, joked that he had planned to sing the ballad himself until he heard her version, and asked her to become the newest member of the Opry.

Underwood covered her face with both hands and cried on the live radio broadcast before nodding yes and hugging him inside the circle of aged Ryman oak. That public co-sign from one of traditional country music’s defining voices quieted critics who still questioned whether a television talent show champion belonged in Nashville’s oldest institution, and fellow Oklahoman Garth Brooks officially inducted her on May 10, 2008.

Rather than letting that March night remain a one-time stage surprise, the two singers returned to the song a year later. In early 2009, Underwood invited Travis to re-record “I Told You So” as a duet, and on March 18, 2009, she brought him onto the *American Idol* stage during the show’s Grand Ole Opry week so the television audience that launched her career could hear them sing it together.

Released to country radio that same week, the new duet climbed to number two on the Billboard country chart, giving Travis his first Top 40 country single since “Three Wooden Crosses” in 2002. At the 52nd Annual Grammy Awards in January 2010, their collaboration won Best Country Collaboration with Vocals.

Two years later, when Travis assembled his 2011 collaborative project *Anniversary Celebration* to mark twenty-five years in the music business, Underwood stepped back into the studio with him to record a new duet of his 1987 hit “Is It Still Over?”

Then, in July 2013, viral cardiomyopathy led to congestive heart failure and a massive stroke that left Travis in a Texas hospital with a slim chance of survival and severe aphasia that took away his ability to speak and sing. During his recovery, Underwood and her husband, Mike Fisher, stayed in contact with Travis and his wife, Mary, offering support as he slowly relearned how to walk and form single words.

When Travis was inducted into the Country Music Hall of Fame on October 16, 2016, in the CMA Theater, Underwood took the stage to honor the mentor who had opened the Opry door for her eight years earlier. Standing before the crowd while Travis smiled from the front row, she sang “I Told You So” directly back to him.

In the years that followed, as Travis began making quiet public appearances alongside Mary, he often showed up to watch Underwood from the side of the stage or the audience. When Underwood celebrated her fifteenth Opry anniversary in May 2023, Travis recorded a video tribute for the occasion, and the two met backstage for a long embrace Whenever their paths crossed in Nashville.

A year later, in May 2024, when Travis released “Where That Came From,” his first new studio recording in more than a decade created with the help of vocal technology and vocalist James Dupré, he sent the track to Underwood early. She publicly celebrated his return to music and spoke on her radio show about what his kindness had meant to her when she was still a newcomer.

That bond came full circle on March 19, 2025, during NBC’s *Opry 100: A Live Celebration*, when Underwood was chosen to lead the centennial salute to Travis with performances of “Three Wooden Crosses” and “Forever and Ever, Amen.”

For the final line of the second song, she walked off the stage steps to where Travis was sitting, placed the microphone in front of him, and smiled as he sang the closing word to a standing room of his peers.

http://www.youtube.com/watch?v=lydBPm2KRaU

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In the late 1980s, Dolly Parton bought back her childhood cabin in Locust Ridge, Tennessee, and paid her brother to keep the two small rooms looking poor. Before her records reached the radio, Dolly was the fourth of twelve children raised there by her mother, Avie Lee, and her father, Robert Lee Parton, a sharecropper who could not read or write. The cabin had no electricity or indoor plumbing. During winter nights, snow drifted through cracks in the timber walls while three or four siblings crowded onto a single straw mattress under patchwork quilts. To keep the draft out, Avie Lee mixed flour paste and glued old newspapers and magazine pages over the inner boards. Outside on the front porch, a barefoot young Dolly held a small guitar and sang into a tin can stuck on a wooden post while her younger brothers and sisters sat in the dirt yard. Once the family moved to a better house, the original land passed to strangers and the cabin began to rot. After opening a replica at Dollywood in 1986, Dolly purchased the real Locust Ridge property back. She hired her brother Bobby to rebuild the structure and brought in her mother to direct every detail from the 1940s, including the wood stove, kerosene lamps, and newspaper walls. Inside the rough timber, Dolly hid modern plumbing, hot water, and air conditioning so her parents and siblings could visit in comfort. She later joked that it cost a fortune to keep the old homeplace looking that poor. Saving every weathered board her father had hammered into place gave Robert Lee a quiet pride in the years he had spent providing for twelve children. Even after decades of stardom, Dolly has continued returning to Locust Ridge alone to cook pinto beans and cornbread in the two rooms where her life began.

On February 2, 1959, Waylon Jennings gave up his seat on a chartered plane out of kindness, then traded a backstage joke with Buddy Holly that haunted him for decades. Just weeks earlier, Jennings was a 21-year-old radio DJ in Lubbock, Texas. Holly, only 22, produced his first record, bought him stage clothes, and hired him on bass for the 24-city Winter Dance Party tour. Across the Midwest, broken bus heaters left the musicians sleeping in overcoats and stuffing newspapers into their boots, and drummer Carl Bunch was hospitalized with frostbitten feet. After the show at the Surf Ballroom in Clear Lake, Iowa, Holly chartered a four-seat Beechcraft Bonanza to Fargo, North Dakota, so his bandmates could rest and wash their clothes. The seats were meant for Holly, Jennings, and guitarist Tommy Allsup. Seeing J.P. Richardson, known as The Big Bopper, struggling with the flu, Jennings gave up his seat, while 17-year-old Ritchie Valens won Allsup’s spot in a coin toss. Earlier that night, Holly and Jennings had squeezed into a photo booth, laughing through a strip of black-and-white pictures. When Holly learned his bass player was taking the bus, he teased that he hoped it froze again. Jennings joked back that he hoped the little plane crashed. Shortly after 1:00 a.m. on February 3, the plane went down in a snow-covered cornfield, killing Holly, Valens, Richardson, and pilot Roger Peterson. Hearing the news that morning, Jennings and Allsup still had to finish the last two weeks of the tour. For decades, Jennings quietly carried the weight of a harmless remark that could never have changed that night. He eventually learned to forgive his younger self, spending the rest of his life making music worthy of the friend who first believed in him.

In 1974, the Bee Gees spent a full week singing at the Batley Variety Club in West Yorkshire while audience members ate fried chicken from wicker baskets at their tables. After the commercial failure of their albums “Life in a Tin Can” and “Mr. Natural,” Atlantic Records refused to release their newest recordings, and American radio treated the trio as a faded 1960s act. Years earlier, the brothers had traveled in limousines before splitting up in 1969. When their career hit bottom five years later, Barry, Robin, and Maurice held together and took the northern English supper-club booking to pay their band and support their families. The turning point came through producer Arif Mardin, who urged them toward R&B, and their friend Eric Clapton, who suggested they leave London for the house at 461 Ocean Boulevard in Miami where he had just rebuilt his own career. In January 1975, the brothers settled near Biscayne Bay and entered Criteria Studios to record “Main Course.” During those sessions, Mardin asked Barry to scream higher at the end of “Nights on Broadway,” drawing out the falsetto that reshaped their sound. Each morning, as the brothers drove across the Julia Tuttle Causeway to the studio, their car tires hit the bridge’s metal expansion joints in a steady rhythm. Barry captured that beat on a small cassette recorder, played it for keyboardist Blue Weaver and drummer Dennis Bryon, and built “Jive Talkin'” around the sound of the bridge. To get past radio prejudice after its May 1975 release, the label sent “Jive Talkin'” to DJs in plain white-label sleeves without the Bee Gees’ name. By August 1975, the song reached No. 1 on the Billboard Hot 100, and the brothers later looked back on their week at the Batley club with gratitude as the lesson in humility that saved them.

In early 1977, inside an 18th-century castle near Paris, the Bee Gees wrote “How Deep Is Your Love” for another singer to record, until their own rough demo changed everyone’s minds. Barry, Robin, and Maurice Gibb had retreated to the Château d’Hérouville in France because of heavy British taxes. The quiet countryside gave the brothers something they needed even more. Years earlier, they had split apart in 1969 and later found themselves playing small northern English clubs when the hits dried up. At the French château, the old fractures had finally healed, and manager Robert Stigwood soon called asking for songs for an untitled film that became “Saturday Night Fever.” They had no script to read. One quiet day, keyboardist Blue Weaver sat at a Fender Rhodes electric piano while Barry described the mood he had in mind. As Weaver played the gentle opening chords, Barry began humming the melody on the spot, and Robin and Maurice soon joined him around the keyboard to build the words together. The brothers originally wrote the ballad for Yvonne Elliman. When Stigwood and the film team heard the fragile family harmony on the demo tape from France, they insisted the Bee Gees keep the song and gave Elliman “If I Can’t Have You” instead. The group later finished the strings and vocals at Criteria Studios in Miami while keeping the original backing track from that first French demo. Released in September 1977, “How Deep Is Your Love” reached No. 1 on the Billboard Hot 100 on Christmas Day, stayed in the Top 10 for a record 17 weeks, and won a Grammy Award. Long after Maurice and Robin passed away, Barry still called that gentle ballad his favorite Bee Gees song, because it held the afternoon the three brothers sat around one keyboard in peace.

In August 1963, Johnny Cash shook hands with four working-class singers at a fair in Virginia and promised them a spot on his tour without signing a single piece of paper. For nine years, Harold Reid, Don Reid, Phil Balsley, and Lew DeWitt had sung gospel harmonies around Staunton, Virginia, calling themselves The Four Star Quartet and later The Kingsmen. Between weekend shows, they supported their families as a delivery truck driver, a mechanic, an auditor, and an office clerk. After learning a rock band had just scored a hit under the name The Kingsmen, they renamed themselves The Statler Brothers after a box of Statler facial tissues sitting in a hotel room. When they drove to the Roanoke-Salem fairgrounds to see Cash perform, an introduction backstage led to an impromptu audition. Cash loved their four-part harmony and promised to bring them on the road as soon as an opening came up. Six months passed without a word. Neighbors in Staunton laughed when the four men claimed they were waiting on Johnny Cash, until the phone finally rang in early 1964. All four quit their steady jobs that same week for tour pay that was actually less than their wages back home. They played their first show with him in Canton, Ohio, on March 8, 1964, and a month later, Cash personally pressured producer Don Law and Columbia Records into giving the unknown quartet a recording contract. They stayed with his road show for eight and a half years, singing at Folsom Prison in 1968 and appearing on his ABC television series along with June Carter, the Carter Family, and Carl Perkins. Cash never signed them to a management deal or took a dime of commission from their earnings, and when they finally left to headline their own tours in 1972, he hugged each man and told them his door was always open.

As a schoolgirl in Timmins, Ontario, Shania Twain hid in the washroom during lunch hour so her teachers would not see she had no food, then later built private rooms inside elementary schools across North America so other children would never have to hide. Growing up in northern Ontario, there were weeks when her family had nothing in the refrigerator except mustard or mayonnaise to spread on a slice of white bread. Afraid that child welfare authorities might separate her siblings if the school found out, she often told teachers she had forgotten her lunch box at home. During sub-zero winters, she slipped plastic bread bags over her socks to keep melted snow from soaking through her worn boots, and she never forgot the day a principal walked into her classroom and set a brown paper bag of donated clothes directly on her desk in front of her classmates. In 2010, she launched the Shania Kids Can foundation to reach elementary students facing poverty and family turmoil at the exact age she had struggled the most. Remembering the shame of that brown paper bag on her desk, she insisted on a strict rule for the program. Instead of handing out charity in public hallways, the foundation builds dedicated spaces called Shania’s Clubhouse inside public schools across Canada and the United States, from Ontario and Niagara to Las Vegas and Nashville. Inside those private rooms, full-time support workers provide hot breakfasts, packed lunches, washers and dryers, one-on-one counseling, and shelves stocked with new winter coats and waterproof boots. During her Caesars Palace residency in Las Vegas, she spent mornings sitting on classroom floors eating breakfast with the students, and she continues to fund the clubhouses by donating one dollar from every concert ticket sold on her major tours.

Shania Twain was born Eilleen Edwards, yet she refused to let Nashville executives take her adoptive father’s last name off her records. After her mother divorced in 1967 and moved three young daughters to the mining town of Timmins, Ontario, she married Jerry Twain, an Ojibwe man from the Mattagami First Nation. Jerry legally adopted Jill, Carrie, and Eilleen, giving them his surname and registering them as official members of the Temagami First Nation. Life in northern Ontario was unforgiving. The family often ran out of heating oil and relied on wild game to survive the winter, yet Jerry quietly gave up his own portions of food so the five children could eat. In her late teens, Eilleen worked alongside him on his reforestation crews, hauling heavy bags of saplings across miles of rock and swamp for weeks without soap or running water. He expected the same hard work from her as the men on the crew, teaching her self-reliance while she composed melodies in her head with dirt on her hands. On November 1, 1987, Jerry and Sharon died in a highway collision with a logging truck north of Wawa, Ontario. At 22, Eilleen put Nashville on hold and took a resort singing job at Deerhurst in Huntsville, using her paychecks to buy groceries, pay bills, and raise her younger half-brothers Mark and Darryl, along with her nephew Zane, until the youngest finished high school. When Mercury Nashville signed her in the early 1990s and asked to change her stage name, she agreed to swap Eilleen for Shania. Giving up Twain or returning to her birth father’s surname was never an option. Whenever reporters later called Jerry her stepfather, she corrected them immediately. The man who raised her in the bush of northern Ontario never lived to hear her records on the radio, so she made sure his name was printed on every single one of them.

Buddy Holly planned to spend the winter of 1959 at home in New York with his pregnant wife, until his manager froze the money his records had earned. After marrying Maria Elena Santiago on August 15, 1958, the 22-year-old singer moved into an apartment at 11 Fifth Avenue in Greenwich Village. He wanted to build his own publishing company, record quiet acoustic songs at home, and produce younger Texas artists like Waylon Jennings so they would be treated fairly. Around that time, a tip from bandmate Joe B. Mauldin’s father-in-law led Holly to look closely at his books, where he discovered that Clovis producer Norman Petty had been funneling the Crickets’ royalties into Petty’s own company accounts while adding his name as a co-writer on several of their hits. When Holly traveled back to New Mexico in late 1958 to separate his finances and ask for his share, Mauldin and drummer Jerry Allison chose to stay in Clovis with Petty and keep the Crickets name. Petty refused to release Holly’s earnings and locked the funds behind a legal dispute. The split left Holly without access to his income just as Maria Elena learned she was pregnant with their first child. Cut off from the money his hit records had already generated, he needed immediate cash to cover their New York rent, upcoming medical bills, and the lawyers hired to recover his royalties. In January 1959, Holly put together a new touring band with Waylon Jennings, Tommy Allsup, and Carl Bunch for the Winter Dance Party, a grueling schedule of 24 Midwest cities in 24 days. Because Maria Elena was dealing with severe morning sickness and both had been troubled by uneasy dreams before departure, he insisted she stay safely behind in New York rather than travel with him as she usually did. Already an international star, Holly spent that subzero January riding buses with broken heaters across the frozen Midwest, starting over from scratch to provide for his wife and unborn child at home.

For his sixth birthday in 1942, Roy Orbison asked for a harmonica, and his father came home from the Texas oil fields with a guitar instead. Born in Vernon, Texas, on April 23, 1936, Roy grew up in a home shaped by long workdays. His father, Orbie Lee Orbison, drilled oil wells and repaired cars, while his mother, Nadine, worked as a nurse. Orbie Lee played guitar after work and knew a harmonica would keep his son from singing while he played, so he saved up for an instrument that let the boy do both. The gift gave Roy a place he struggled to find outdoors. Born with severely poor eyesight, he wore thick glasses from early childhood and stayed away from the rough sports common in West Texas oil towns. At night, Orbie Lee came home with grease still worked into his calloused hands and sat beside Uncle Charlie to guide Roy’s small fingers through his first chords on “You Are My Sunshine.” Those lessons soon earned Roy a rare privilege in the family living room. On nights when relatives gathered to sing through the lean war years, he was allowed to stay up past bedtime to play along with the adults. By 1944, at age eight, the shy boy won first prize in a youth talent contest on local radio station KVWC in Vernon. When the family relocated to the oil town of Wink in 1946, that guitar traveled carefully with them. Three years later, at age thirteen, Roy formed his first band, the Wink Westerners, turning the quiet confidence he found beside his father into the beginning of a lifelong career in music.