About the Song

In 1967, Waylon Jennings released one of his most thoughtful and understated albums—Waylon Sings Ol’ Harlan—a tribute to one of country music’s most revered songwriters, Harlan Howard. Known for penning songs with plainspoken poetry and emotional honesty, Howard found a kindred voice in Waylon. And nowhere is that connection more beautifully felt than in the tender track “Woman, Let Me Sing You a Song.”

Before the outlaw era fully took hold, before the leather vests and rebellious image, Waylon Jennings was already showing signs of the deep emotional conviction that would shape his career. “Woman, Let Me Sing You a Song” is a quiet offering—a ballad of affection, humility, and the simple power of music as a way to reach the heart.

There’s no swagger here, no bravado. Just a man with a guitar and a voice full of warmth, asking for a moment to sing—not to impress, but to connect. Waylon’s vocal delivery is calm and sincere, bringing out the gentle plea in Howard’s lyrics. The instrumentation is classic 1960s Nashville—easy on the ears, led by acoustic guitar, subtle steel, and soft rhythm—leaving room for the story to unfold.

This song isn’t about grand gestures. It’s about the quiet moments between two people—the kind that aren’t written in letters or shouted from rooftops, but sung slowly in dim-lit rooms, just to let someone know they’re loved.

For those who admire the roots of country songwriting, “Woman, Let Me Sing You a Song” is a reminder of what the genre does best: it speaks directly to the heart, with no need for decoration. Just truth, melody, and feeling. And Waylon Jennings, even in the early years, knew how to carry all three with grace.

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