The Greatest Oldies Music

Country

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 the street at the Ryman Auditorium.

She and Doolittle had reached Nashville late the night before. “I’m a Honky Tonk Girl” was climbing the charts, and Loretta finally had an invitation to perform on the Grand Ole Opry.

They just did not have enough money for a hotel.

Sleeping Across From the Ryman

Doo parked the car across from the Ryman, and they spent the night there.

The next morning, Loretta opened her eyes to the building she had once known only through Grand Ole Opry broadcasts back in Kentucky.

Doo returned with a box of doughnuts.

That was breakfast.

Across the street was the stage she had dreamed about.

Promoting the Record Themselves

Only months earlier, Loretta and Doo had been driving from radio station to radio station with copies of “I’m a Honky Tonk Girl.”

They carried the records themselves, introduced Loretta to disc jockeys and asked stations to play the song.

There was no major Nashville organization carrying her yet.

Loretta was twenty-eight, already the mother of four, and learning the music business from the road.

One Song for the Opry

On October 15, 1960, Loretta walked into the Ryman wearing a short, tight dress she had made herself.

She had one record to sing.

Loretta later remembered being so nervous that after leaving the stage, she realized she had barely heard herself perform. She remembered tapping her foot and remembered the room around her.

Doo experienced the moment differently.

He was outside in the car.

Listening From Across the Street

While Loretta stood on the Opry stage, Doo turned the radio dial and tried to pick up the broadcast from the car.

The image captured how close they were to Nashville and how far they still had to go.

Loretta was inside the Ryman performing.

Her husband was across the street listening through a radio because the life surrounding that stage had not yet opened completely to them.

The Hard Work Was Still Ahead

The appearance did not instantly make Loretta Lynn a star.

She still had to work with the Wilburn Brothers, leave Zero Records, sign with Decca and develop the sharper songwriting voice behind records such as “You Ain’t Woman Enough,” “Don’t Come Home a-Drinkin’” and “Fist City.”

In 1962, she became an official member of the Grand Ole Opry.

By then, Nashville no longer had to be heard from a parked car.

What the Street Outside the Ryman Really Leaves Behind

The distance between where Loretta slept and where she sang that first night was only a street wide.

On one side sat a car containing her husband, a box of doughnuts and nearly everything they could afford.

On the other stood the Ryman.

Loretta crossed that street with one record and a homemade dress.

Years later, she would become one of the women who changed what country music was allowed to say.

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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.

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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.

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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.

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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.

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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.