Introduction
For those of us who’ve walked a few winding roads and learned to embrace life’s quirks, Waylon Jennings’ performance of I’ve Always Been Crazy with The Waymore Blues Band, captured in the 2000 Never Say Die: The Final Concert Film, is a powerful ode to living unapologetically. Recorded at Nashville’s historic Ryman Auditorium, this rendition from January 5-6, 2000, showcases Jennings at his most raw and resolute, his voice carrying the weight of a life lived on his own terms. Backed by a stellar ensemble he called “the band I always wanted,” this song—originally released in 1973—takes on new depth in this live setting, blending outlaw country grit with a reflective wisdom that resonates with those who’ve seen enough years to appreciate authenticity. Let’s dive into this unforgettable moment and explore why it stands as a testament to Jennings’ enduring legacy.
Waylon Jennings, a towering figure in the outlaw country movement, had already redefined the genre by 2000, with hits like Good Hearted Woman and a career that challenged Nashville’s polished norms. I’ve Always Been Crazy, written by Jennings himself, is a self-portrait of a man who owns his contradictions: “I’ve always been crazy, but it’s kept me from going insane.” In this live performance, delivered from a chair due to health struggles with diabetes and emphysema, Jennings’ defiance shines through. The lyrics speak of a life spent dodging trouble—“I don’t know why I keep on running, I guess I’m having too much fun”—yet there’s a seasoned perspective here, a nod to the resilience it takes to stay true to oneself. For older listeners, it’s a song that mirrors the freedom and cost of carving your own path, mistakes and all.
Musically, this version of I’ve Always Been Crazy is a triumph of country-rock energy. The Waymore Blues Band, a blend of longtime Waylors like drummer Richie Albright and newer talents like guitarist Reggie Young, brings a muscular edge with tight rhythms and a bold horn section—an ambitious choice for Jennings’ late-career sound. The arrangement kicks off with a driving guitar riff, setting a rebellious tone that matches the song’s spirit. Jennings’ vocals, weathered yet commanding, carry a lived-in authenticity, each phrase dripping with attitude and humor. The band’s interplay—crisp drums, soulful horns, and a steady bassline—creates a backdrop that’s both loose and polished, giving Jennings room to shine. For those who’ve followed his journey, it’s a sound that evokes nostalgia for the 1970s outlaw era while proving his relevance at the turn of the millennium.
What makes this performance so compelling is its honesty. Jennings doesn’t shy away from his struggles—physical or otherwise. Between verses, he jokes about his health, saying, “I can still kick ass, you’ve just got to bring ‘em up here,” a quip that draws laughs and underscores his never-say-die ethos. The song itself is a celebration of individuality, acknowledging the chaos of a wild life—“I’ve done things I’m not proud of, but I’ve never hurt no one”—while finding peace in it. For an audience with a few decades behind them, this hits home: it’s a reminder that imperfection doesn’t dim a life well-lived, and that owning your story is its own kind of victory. Jennings’ delivery feels like a conversation with old friends, his gravelly voice a beacon for anyone who’s ever felt like an outsider.
The Ryman setting adds a layer of reverence to the performance. Known as the “Mother Church of Country Music,” it was a fitting stage for Jennings, who’d fought Nashville’s establishment to redefine the genre. The Never Say Die concerts weren’t billed as a farewell, but they carried a weight, with Jennings joined by guests like Jessi Colter, Travis Tritt, and John Anderson. Yet I’ve Always Been Crazy stands out as a solo declaration, a moment where Jennings and his band claim the spotlight. For fans who caught his earlier days or tuned into his later specials, it’s a song that distills his outlaw spirit—fierce, funny, and unflinchingly real. Its inclusion in the 2007 expanded CD/DVD release cemented its place as a highlight of his final bow.
Reflecting on I’ve Always Been Crazy today, it’s more than a song—it’s a snapshot of Waylon Jennings at his core: a man who lived boldly, loved fiercely, and sang truthfully. For those of us who’ve navigated life’s twists and turns, it’s an anthem of self-acceptance, urging us to embrace our own brand of crazy. The Waymore Blues Band amplifies this spirit, their energy a tribute to a legend who never backed down. In a world that often demands conformity, this performance is a call to stay true, to laugh at the chaos, and to keep running toward what makes you feel alive. Jennings left us too soon in 2002, but this song ensures his voice still rings loud, crazy and all.