By the end of the 1980s, Waylon Jennings had nothing left to prove in country music. He had 16 No. 1 country hits and a place at the center of the Outlaw movement. What he did not have was a high school diploma. In 1989, at 52 years old, he set out to get one, studying on his tour bus with his 10-year-old son, Shooter, helping him through the math.

The Benefit Show in Kentucky

Waylon Jennings later said the whole thing started by accident. He had agreed to play a benefit for Martha Wilkinson, the wife of Kentucky Governor Wallace Wilkinson, and he did not know what the money was for until the show was over. When he asked, he was told it was for the GED program.

So he went back out and told the crowd what he thought of it. As he recalled it to a reporter in 1990, he said the GED program was great, because he had quit school in the tenth grade and had always regretted never getting a high school diploma.

Martha Wilkinson had made adult education her cause as first lady, building a campaign to get Kentucky dropouts to earn their GED certificates. In Waylon’s own words, when he walked off that stage, she “was all over me.”

What He Had Been Telling Shooter

There was a second reason the idea stuck. Waylon Jennings had undergone heart bypass surgery near the end of the 1980s, and he later said the recovery gave him time to look hard at the gap between what he told his son and what he had done himself.

“I’d been preaching to Shooter about the importance of education. But here I was, a high school dropout.”

He had told the boy that quitting school was the worst mistake he ever made. He said it still felt like just words. “I never did like folks who didn’t practice what they preached,” he explained.

School had not ended well for him the first time. Waylon Jennings left Littlefield High School in West Texas in the tenth grade, and one biography says the school superintendent encouraged the teenager to go. He went to work and into radio, and music did the rest.

Studying on the Tour Bus

He took instructional GED tapes on the road and worked through them on his bus. Contemporary reports say the tapes came by way of Martha Wilkinson; later accounts identify them as the GED on TV lessons from Kentucky Educational Television.

The hardest part was math, and that is where Shooter came in. Waylon said his son helped him with fractions, “something I failed at,” and with algebra. He never pretended the algebra came easy. Talking to a reporter afterward, he joked that there ought to be treatment centers for people who understand algebra.

Passing the Test

Waylon Jennings passed the GED exam in December 1989 and picked up his certificate in January 1990, which is why some sources list one year and some the other. He received it from Martha Wilkinson, the same woman who had pressed him after that benefit show.

He did not treat it as a small thing. He counted it among the biggest accomplishments of his life, and he was plain about who it was for.

“I did it for me and I did it for my son.”

The Poster Boy

The man who had spent years as country music’s best-known rebel spent the early 1990s visiting schools, talking to kids about staying in school and staying away from drugs. He had quit drugs himself less than a decade earlier. “I’m the poster boy for high school equivalents,” he told a reporter in 1993.

By then, he was wearing a ring from Littlefield High School, the school he had left nearly four decades earlier.

That school is still there. Its address today is on Waylon Jennings Boulevard.