Waylon Jennings Songs: A List of 20 of the Best | Holler

About the Song

In the mid-1970s, when country music was shifting toward a bolder, more personal style, Waylon Jennings stood at the very heart of the movement. His 1975 album Dreaming My Dreams is often hailed as one of his greatest achievements — a record that helped define the Outlaw Country sound. Nestled within this landmark album is “She’s Looking Good,” a track that may not carry the rebellious edge of some of Waylon’s anthems, but instead reveals his talent for tender storytelling and smooth delivery.

Originally written and recorded by other artists before Waylon brought it into his own orbit, the song becomes uniquely his thanks to that rich, commanding baritone. Waylon Jennings had a way of making even the simplest lyric feel personal, and in “She’s Looking Good” he takes what could be a straightforward compliment and infuses it with admiration, respect, and warmth. The result is a portrait not just of physical beauty, but of presence — the way someone can light up a room with confidence and grace.

Released in 1975, the track reflects the strength of Waylon’s artistry during a turning point in his career. While Dreaming My Dreams would be remembered for hits like the title track and “Are You Sure Hank Done It This Way,” this song adds balance to the record. It shows that beneath the outlaw image — the leather, the grit, the rebellion against Nashville norms — Waylon also carried a deep appreciation for life’s softer, more tender moments.

What makes “She’s Looking Good” enduring is its sincerity. It is a reminder that even the toughest voices in country music could stop and acknowledge beauty in its purest form. For fans, the song is more than just a compliment set to music; it’s a glimpse of Waylon’s versatility, his ability to honor a subject with honesty and without pretense.

Through “She’s Looking Good,” Waylon Jennings proves once again why his music resonates across generations: not because of flash or fashion, but because of his unmatched ability to tell the truth in song — whether that truth came wrapped in rebellion, or, as here, in admiration.

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