There’s a grin behind Toby Keith’s “How Do You Like Me Now?!” that makes its wounded pride even more entertaining. Co-written with Chuck Cannon and released in November 1999, it spent five weeks atop Billboard’s country chart and became the biggest country hit of 2000. I’ve always enjoyed the satisfaction in its story: the small-town boy dismissed in high school finally gets his chance to be heard. Toby gives him plenty of swagger, but you can still hear how much the rejection stung. That lingering hurt makes the boast work. He’s successful now—and he wants someone who doubted him to notice.

Toby Keith’s How Do You Like Me Now?!: A Triumphant Ballad of Redemption Toby Keith’s How Do You Like Me Now?! is more than just a country anthem; it’s a…

Toby Keith had a gift for telling a ridiculous barroom story as though it had happened to someone you knew. In “The Size I Wear,” co-written with Rivers Rutherford for his 2012 album *Hope on the Rocks*, two friends settle in for beers before a group of secretaries gives the evening a new direction. What I enjoy most is the mischief in his delivery. He lets the situation get out of hand without sounding remotely surprised. A few drinks, a little misplaced confidence, and suddenly there’s a story somebody will have to explain the next morning. Toby knew exactly how to land that kind of joke.

Toby Keith’s “The Size I Wear”: A Deep Dive into Americana Toby Keith’s “The Size I Wear” is more than just a catchy country tune; it’s a cultural artifact that…

Marty Robbins’s tribute to his wife reached record stores on January 23, 1970. Four days later, he underwent triple bypass surgery at Nashville’s St. Thomas Hospital. He had gone in expecting a checkup and permission to race that spring. Although he had suffered a heart attack while touring Ohio the previous August, he told reporters he had felt well since. The tests revealed two blocked arteries and a third that was 75 percent obstructed. “I came and took them and found out nothing was all right,” he said. The January 27 operation was the first triple bypass performed at St. Thomas, at a time when the procedure was still uncommon. One doctor described Marty as having entered surgery hanging by a thread. Meanwhile, listeners were discovering “My Woman, My Woman, My Wife,” written for Marizona. They had met at an ice cream parlor in Glendale, Arizona. She wanted to marry a singing cowboy; he was singing in Phoenix clubs and struggling to make a living. They married on September 27, 1948, the day after his twenty-third birthday. Marizona was eighteen. By the spring of 1970, the song had reached No. 1. “My wife is everything I said in the song,” Marty explained. “It’s a true song.” Recovery brought him back to racing that fall. His appetite for it survived the surgery: at Charlotte in 1974, he drove into a wall at roughly 160 miles an hour to avoid Richard Childress’s stalled car. He needed 37 stitches in his face. On December 8, 1982, another heart attack and emergency surgery ended differently. Marty died at St. Thomas at 57, with Marizona and their children at the hospital. They had been married for 34 years. The young singer she had met in Arizona had become a country star, and among the records he left behind was his own account of what she had meant to him.

On January 23, 1970, Columbia Records released a new Marty Robbins single called “My Woman, My Woman, My Wife.” It was a plain, grateful love song, and Marty never pretended…

Waylon Jennings had plenty of songs that could rouse a crowd. When he named his favorite recording on an Austin stage nearly a decade later, he chose the tender “Dreaming My Dreams with You.” He recorded it in 1975, during the years that established his outlaw reputation. Fans knew the black hat, the leather-covered Telecaster, and a voice with enough grit to make defiance sound effortless. Here, that voice carried resignation. Waylon sang slowly, letting the hurt emerge without pushing it. The man in the song understood that love might end while the longing remained. There was little anger in his delivery. He left room for affection, regret, and the possibility that someone could leave his life without ever leaving his dreams. The single reached No. 10 on the country chart. Its place in Waylon’s own affections was clearer when he introduced it years later: “I guess this is my favorite song I ever recorded.” For a singer so closely associated with independence, it was a revealing choice—a performance in which he allowed himself to sound completely unable to let go.

Waylon Jennings gave country music some of its rowdiest anthems. But when he was asked which of his own recordings meant the most to him, he didn’t pick an outlaw…

Charley Pride could make a chorus feel welcoming before he reached the second line. In “Does My Ring Hurt Your Finger,” that familiar warmth makes the heartbreak harder to hear. He sings with a gentleness that leaves little room for anger. There is no confrontation, no demand for an explanation. He asks whether her wedding ring is uncomfortable and offers to have it loosened. The practical solution is almost unbearable. He can arrange to fix the ring. Whatever has made her stop wearing it is harder to address. Pride lets that realization sit beneath his courteous delivery. The voice remains steady, even as the question reveals how much the answer matters. For listeners who know his easy smile and cheerful hits, this performance offers something quieter: a husband approaching a painful suspicion as carefully as he can, hoping she will give him another reason.

The song is “Does My Ring Hurt Your Finger,” and if you only know Charley Pride from his sunny, sing-along hits, it can catch you off guard. Released in 1967,…

Marty Robbins wrote “Two Little Boys” for Jean Shepard after Hawkshaw Hawkins died. Then he placed her sons’ names in the songwriting credit, giving them the financial benefit of a song about the father they had lost. Hawkshaw died on March 5, 1963, in the plane crash that also killed Patsy Cline and Cowboy Copas. Jean was 29, eight months pregnant, and caring for their fifteen-month-old son, Don Robin, whose name partly honored Marty. Before leaving that morning, Hawk had looked into Don’s crib and said he wanted another child just like him. Their second son, Harold Franklin Hawkins II, arrived 34 days after the crash. For months, Jean stayed away from performing. Her parents moved in to help, she sold Hawk’s quarter horses, and she considered leaving music altogether. Opry president Jack DeWitt encouraged her to return. Later in 1963, Marty approached her outside a Nashville publishing office. He wanted to write about her loss. Jean told him he couldn’t possibly know how she felt. He wrote the song anyway. After hearing it, she conceded that he had done a “pretty damn good job.” On January 27, 1964, Jean recorded “Two Little Boys” alongside “Second Fiddle (To an Old Guitar).” Capitol paired them on a single. “Second Fiddle” reached No. 5, giving her a chart comeback after five years without one. On the other side was Marty’s gift: a song that acknowledged what Jean was raising her sons without, and writing credits that helped provide for them.

In January 1964, ten months after Hawkshaw Hawkins died in the plane crash that also took Patsy Cline, Cowboy Copas and pilot Randy Hughes, his widow Jean Shepard went into…

As Parkinson’s disease made performing harder for Jeff Cook, Alabama kept his microphone onstage. Whether he could join them that night or not, his place remained. Jeff had formed the band with cousins Randy Owen and Teddy Gentry in Fort Payne, Alabama. They spent six years playing for tips at The Bowery in Myrtle Beach before finding their breakthrough. Twenty-one consecutive No. 1 hits followed. Jeff’s guitar, fiddle and keyboards helped build the sound audiences came to recognize. The first warning appeared away from music: he struggled to cast a fishing lure. Later, he began missing notes. Jeff suspected a pinched nerve; Randy and Teddy worried he had suffered a stroke. Doctors diagnosed Parkinson’s. He kept the diagnosis private for years. As his symptoms became more noticeable, some people mistook his unsteadiness for drinking. Randy later said those rumors were especially painful. He and Teddy wanted to defend their friend, but respected his decision to keep his health private. In April 2017, Jeff told fans what was happening. He also made clear that he wanted the band to continue. “We could hire 10 people, but we can’t replace Jeff Cook in the group Alabama,” Teddy said. Additional musicians helped cover his parts. His microphone stayed where it belonged. Randy, meanwhile, spoke openly about how difficult it was to find the same drive without Jeff beside him. Continuing meant adjusting to the absence of someone who had shared the work from the barroom years onward. Jeff died at his home in Destin, Florida, on November 7, 2022, at 73. Long before that final goodbye, his bandmates had found a simple way to keep welcoming him: a microphone waiting whenever he could return.

\ In April 2017, Jeff Cook, Randy Owen and Teddy Gentry sat down together with The Tennessean in Nashville. For years, the three cousins who built Alabama had kept a…

Two weeks before Doo Lynn died, Loretta took him to get hearing aids. He had told her he could no longer hear her sing. At first, she misunderstood. She thought he meant he didn’t want to listen anymore. Then she realized he was describing something he had lost. By the summer of 1996, Loretta had spent years caring for her ailing husband. Their marriage had endured nearly five decades of affection, conflict and music. Doo had bought her first guitar and encouraged her to perform. Now he was struggling to hear the voice he had helped introduce to the world. The hearing aids gave them a little time. Four years after his death, Loretta recorded “I Can’t Hear the Music,” drawing on that experience. Getting through the session was difficult. As she cried, Randy Scruggs encouraged her to concentrate on something she wanted—anything that might help her finish singing. “He was my biggest critic and my greatest fan,” she said. She rarely performed the song onstage. But in 2021, on what would have been their 73rd wedding anniversary, her Instagram shared footage of a live performance from 2000, interspersed with scenes of her and Doo together. Loretta was 88 when the clip was posted. The title carried a painful reversal. Near the end of his life, Doo had needed help hearing her music. After he was gone, Loretta used those words to describe the absence he left behind.

In the summer of 1996, Oliver “Doolittle” Lynn told his wife he couldn’t hear the music anymore. Loretta Lynn thought he was tired of it. She was wrong, and four…

Stevie Nicks married her closest friend’s widower believing she could help hold his family together. The marriage lasted about three months. Her connection to the little boy at its center endured far longer. Robin Anderson had known Stevie since their school days, before Fleetwood Mac and the fame that followed *Rumours*. In 1982, Robin developed leukemia while pregnant. She delivered her son, Matthew, prematurely and died only days later. Stevie’s visits during Robin’s illness also exposed how troubled her own life had become. She later recalled arriving high on cocaine until Robin told her not to come back in that condition to a place where people were fighting to live. After Robin died, Stevie became convinced that marrying her husband, Kim Anderson, would allow her to care for Matthew. Those close to her questioned the decision. Looking back, Stevie called it “insanity.” She acknowledged that she did not love Kim as a husband; grief and devotion to Robin had led her into a commitment she could not sustain. One memory became central to how she understood that mistake. Stevie said Matthew’s cradle seemed to rock whenever she entered the nursery, something she interpreted as Robin’s presence. When she later found it still, she took that as a sign that Robin would not have wanted the marriage. It was Stevie’s way of making sense of a decision she had begun to recognize was wrong. She and Kim separated, ending the marriage in 1983. Years later, Stevie reconnected with Matthew, helped support his education and remained involved in his life. He eventually became a father himself and named his daughter Robin. When the little girl took Stevie’s hand and called her “Grandma Stevie,” the connection no longer depended on a marriage or an attempt to take her friend’s place. It had grown through the years they continued to share. Stevie could not undo Robin’s death or make the family whole in the way she had first imagined. She did, however, remain part of Matthew’s life long enough to know the daughter carrying his mother’s name.

STEVIE NICKS TRIED TO REBUILD HER BEST FRIEND’S FAMILY AFTER DEATH—THEN REALIZED GRIEF HAD TAKEN HER TOO FAR The image Stevie Nicks remembered from her only marriage was not the…

Loretta Lynn spent the night before her Grand Ole Opry debut sleeping in a car across from the Ryman Auditorium. When she woke in the passenger seat, the building she had imagined for years was right outside the window. She and her husband, Doolittle, had arrived in Nashville late and couldn’t afford a hotel. Doo found a place to park, and they stayed there until morning. He returned with doughnuts for breakfast. “I’m a Honky Tonk Girl” had brought them this far. For months, they had driven between radio stations, carrying copies of the record and asking disc jockeys to play it. As the song climbed the country charts, Loretta received the invitation she had dreamed of while listening to the Opry back in Kentucky. At twenty-eight, she was raising four children and trying to establish a career without the support of a major Nashville label. On October 15, 1960, she entered the Ryman in a short, fitted dress she had sewn herself. She performed the song she and Doo had worked so hard to get heard. Her memories of the appearance were fragments of overwhelming nerves. She recalled the room and the movement of her foot keeping time, but afterward she could barely remember hearing her own voice. Outside, Doo was in the car, working the radio dial to hear his wife sing from the building across the street. The debut opened a door, but years of work remained. With help from the Wilburn Brothers, Loretta secured her release from Zero Records and signed with Decca. She joined the Opry in 1962, then developed the direct, unmistakable songwriting voice behind “You Ain’t Woman Enough,” “Don’t Come Home a-Drinkin’” and “Fist City.” That first visit held none of the comforts her success would eventually bring. There was a car to sleep in, doughnuts in the morning, and a homemade dress for the performance. Across the road was the stage she had come to sing on—and a husband outside trying to hear it happen.

LORETTA LYNN SLEPT IN A CAR ACROSS FROM THE STAGE SHE DREAMED OF SINGING ON Loretta Lynn woke up in the passenger seat of a parked car and looked across…

You Missed

Marty Robbins’s tribute to his wife reached record stores on January 23, 1970. Four days later, he underwent triple bypass surgery at Nashville’s St. Thomas Hospital. He had gone in expecting a checkup and permission to race that spring. Although he had suffered a heart attack while touring Ohio the previous August, he told reporters he had felt well since. The tests revealed two blocked arteries and a third that was 75 percent obstructed. “I came and took them and found out nothing was all right,” he said. The January 27 operation was the first triple bypass performed at St. Thomas, at a time when the procedure was still uncommon. One doctor described Marty as having entered surgery hanging by a thread. Meanwhile, listeners were discovering “My Woman, My Woman, My Wife,” written for Marizona. They had met at an ice cream parlor in Glendale, Arizona. She wanted to marry a singing cowboy; he was singing in Phoenix clubs and struggling to make a living. They married on September 27, 1948, the day after his twenty-third birthday. Marizona was eighteen. By the spring of 1970, the song had reached No. 1. “My wife is everything I said in the song,” Marty explained. “It’s a true song.” Recovery brought him back to racing that fall. His appetite for it survived the surgery: at Charlotte in 1974, he drove into a wall at roughly 160 miles an hour to avoid Richard Childress’s stalled car. He needed 37 stitches in his face. On December 8, 1982, another heart attack and emergency surgery ended differently. Marty died at St. Thomas at 57, with Marizona and their children at the hospital. They had been married for 34 years. The young singer she had met in Arizona had become a country star, and among the records he left behind was his own account of what she had meant to him.