Tenderness in a Country Tough Guy

When I mentioned to Bob Dylan during an interview in the late 1970s that I was going to Nashville to see Waylon Jennings, Dylan said, “I love Waylon. Why don’t you get him to record one of my songs?”

I thought the often enigmatic Dylan was kidding, but when I saw him again three years later, the first thing he asked was, “What ever happened with Waylon?”

In retrospect, I shouldn’t have been surprised by Dylan’s affection. If I ever wrote a song, I’d want to write it like Bob Dylan and then sing it like Waylon Jennings.

Jennings, who died Wednesday at age 64, was the ultimate honky-tonk hero--someone whose voice conveyed a confidence and strength that made him (and our dreams) seem invincible, but also found room for a trace of teardrop.

You’re going to see the words “tough,” “rebellious” and “outlaw” a lot in tributes to the West Texas native, but the quality that always struck me most about Jennings was his tenderness.

Beneath the macho surface of all those songs that he and Willie Nelson used to define the country “outlaw” movement of the ‘70s, there was a vulnerability that gave the music a rare richness and heart.

One of Jennings’ most popular recordings was “Amanda,” a Bob McDill song that Jennings performed so convincingly it was hard to believe he didn’t write it himself. The lines that got the most applause:

It’s a measure of people who don’t understand

The pleasures of being in a hillbilly band

I got my first guitar when I was 14

Now I’m over 30 and I’m still wearing jeans.

It was a great anthem because it captured the romance of the outlaw movement, which was all about growing up without surrendering youthful dreams. I’ve seen people raise a beer to those lines across the country, from stadiums to honky-tonks.

But another part of the song meant the most to Jennings and best explains how he was able to inject a lyric with such deeply rooted emotion.

Amanda, light of my life

Fate should have made you

A gentleman’s wife.

“That line hits hard every time I sing it,” Jennings told me in 1990. “I think of Jessi.”

Jennings had been married for more than 20 years at that point to singer-songwriter Jessi Colter, who set aside her own promising career to stand at his side during long periods of career frustration and cocaine addiction.

“She was what made me finally quit [drugs],” he continued. “I looked at her face one day, and I could see what I was doing to her, the pain I was causing. Nothing else had been enough. ... The fact that I almost ruined my voice, that I couldn’t even see straight some nights.”

Colter’s love was a central theme in Jennings’ life and his music. She was his fourth wife, and he went through periods so dark that most women would have given up. She’s the one he wrote “Good Hearted Woman” about, and the one he had in mind when he sang Lee Clayton’s “Ladies Love Outlaws.”

Colter’s devotion not only helped Jennings tame his demons, but also filled him with an inner richness that enabled him to bring a deeper dimension to his music.

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I was a fan of Jennings from the moment I heard him in 1966. He was third-billed on a country music tour featuring Hank Williams Jr. and Loretta Lynn at the old Long Beach Auditorium.

Interviewing Williams backstage, I could hear this great voice through the rickety old dressing room door. I didn’t know anything about Jennings, but I was so enthralled with the voice that I cut the interview short and moved to the side of the stage.

Even in those early days, Jennings had the charisma of a young Elvis Presley, and his rugged vocals had an authority and emotional punch remindful of the best country and rock music. He grew up on country, but he didn’t limit himself to the old themes of trains and prisons and mama’s love.

He sang about relationships and dreams in ways that enabled him to reach out in the ‘60s to such unconventional pop and rock fare as the Beatles’ “Norwegian Wood (This Bird Has Flown)”--not as part of some clever crossover campaign, but because he knew it was a good song.

John Lennon later told me that it was one of his favorite versions of a Beatles song.

I couldn’t believe in 1966 that Jennings wasn’t already a superstar in Nashville. The problem was that he resisted the town’s old-fashioned way of doing things. They didn’t like it when he wanted to use his own band on records or pick the songs he would record, or when he refused to wear rhinestone suits.

By the early ‘70s, Jennings’ spirit was broken. Despite a few Top 20 country hits, he was deeply in debt and drained emotionally. For a moment in 1971, he even thought about quitting the business. “I didn’t really know what to do,” he recalled years later in an interview. “I just felt all burned out inside. I was really down, and it felt like people were still trying to kick me.”

Again it was Colter who helped him find the strength to fight back against the Nashville establishment--and with sidekick Willie Nelson, he won big with the outlaw movement.

Through such hits as “Mammas Don’t Let Your Babies Grow Up to Be Cowboys” and “Luckenbach, Texas (Back to the Basics of Love),” the pair drew millions of new fans to country music with real, inspiring work.

I was such a fan that I broke a Times rule in 1972 and wrote the liner notes for Jennings’ “Ladies Love Outlaws” album, figuring no one at the paper would ever see it because Jennings wasn’t known outside of country music.

In the notes, I recalled an evening in 1971 at the old Palomino club in North Hollywood when Phil Spector, the legendary record producer, was so excited by Jennings’ performance that he stood and cheered after every song.

“He ought to have a No. 1 record every time,” Spector shouted.

And he was right.

Jennings started heating up in Nashville in 1974 when he had two No. 1 singles in a row. That same year, after a show one night in Las Vegas, he played me a tape of his upcoming album, “The Ramblin’ Man.” He was uncertain about which track to release as a single and asked for a suggestion. I mentioned “Rainy Day Woman,” a rousing, feel-good, guitar-driven tune.

When the single soared up the charts, Jennings called to thank me for the suggestion, but I always felt a little guilty about it.

“Rainy Day Woman” only went to No. 2.

Like Spector, I thought everything Jennings did in those days should have been No. 1.

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Despite diabetes-related health problems that resulted in the amputation of his left foot in December, Jennings always counted his blessings.

The last time I saw him was about a year ago when he came to town on business.

We had breakfast at a hotel near the Beverly Center, and it was painful to see this once-dynamic figure hobble from the elevator, leaning on a cane for support. I tried to hide my surprise at his condition, but he seemed to sense to my mood.

“Hey,” he said. “I’m a lucky man. My dreams did come true.”

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Robert Hilburn is at robert.hil burn@latimes.com.