About the Song
Released in 1985 on the compilation album The Waylon Jennings Files, Vol. 10, “It’s Sure Been Fun” feels like a heartfelt reflection from a man who’s lived long on the road, through the highs, heartbreaks, and unrelenting spirit of country music. Though this song didn’t rise as one of Jennings’ commercial hits, it stands out as a soulful meditation on gratitude, friendship, and the passage of time.
From the opening chords, the song carries that unmistakable Waylon ease—laid-back yet filled with meaning. His baritone, as warm as aged oak, tells the listener: I’ve seen enough to know what matters. There’s no bravado here, no defiance. Instead, Jennings sings with a kind of peaceful satisfaction, looking back on the rough roads and long nights not with regret, but with appreciation.
Musically, “It’s Sure Been Fun” blends classic outlaw country textures with a gentle, reflective tempo. The guitars are clean and melodic, the rhythm section steady but subdued, leaving space for Jennings’ voice to do what it does best—carry truth. His delivery feels like he’s talking directly to an old friend, perhaps even to the audience that followed him through decades of change.
For older listeners, this track holds special resonance. It speaks to the wisdom that comes with age: understanding that life, with all its storms, was still worth every mile. The phrase “It’s sure been fun” isn’t said with irony—it’s a genuine thank-you, an acknowledgment of both struggle and joy.
In the broader arc of Waylon Jennings’ career, this song acts like a quiet chapter at dusk—a moment to pause, smile, and remember. It may not thunder like his outlaw anthems, but it hums with the kind of peace that only comes when a man has made his mark and can finally say, with full heart and steady voice, it’s sure been fun.