The Greatest Oldies Music

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Country

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.

Country

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.

Country

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.

Country

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.