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It was a steamy summer day in Franklin last Wednesday, two living legends — Willie Nelson and Bob Dylan—rolled into FirstBank Amphitheater as part of the Outlaw Music Festival, and I finally got to check off a massive item on my musical bucket list. I’d never seen Bob Dylan or Willie Nelson live before. At 84 and 92 respectively, I wasn’t sure what to expect going in. Let’s just say I went in with low expectations… and walked out absolutely satisfied.
The show was at our favorite outdoor venue, FirstBank Amphitheater—also known around here as the “Red Rocks of the South.” Tucked into a stunning limestone quarry, it was the perfect setting for a night steeped in American roots music. A big thank you to our friends at FirstBank Amphitheater for giving us the VIP treatment. It was our first time experiencing the Quarry Club, and it made the night even more memorable with water view, cool drinks, and a relaxed vibe that took the edge off the heat.
Speaking of heat—it was a scorcher. But that didn’t stop folks from ages 5 to 95 from turning out in droves, filling the quarry with fans from every generation. It was a rare, beautiful thing to see that kind of cross-generational crowd brought together for one night of music history.
Tami Neilson kicked off the evening with fiery energy and undeniable charisma, followed by the soul-stirring Nathaniel Rateliff & The Night Sweats, who powered through the sweltering temperatures with a tight, energetic set. Willie’s longtime harmonica player, Mickey Raphael, made a surprise appearance during Rateliff’s set—setting the tone for a night full of surprises and musical magic.
Then came Bob Dylan, perched behind the piano for most of the set, occasionally playing his harmonica. Yes, the arrangements were different—he played many of his classics like “Gotta Serve Somebody” and “The Times They Are A-Changin’” in altered, jazzier renditions—but that’s Dylan. You don’t go to hear him recreate the records; you go to experience him. His presence, his phrasing, his defiance of expectation—it was all there, and it was captivating.
Next, I was amazed at how sharp Willie Nelson remains. Most of us could only hope to be in that shape at 92. With his battered guitar Trigger slung over his shoulder, he played through his set with energy and purpose, riffing like a man half his age. He had help on vocals from the soulful Waylon Payne, who added a rich layer to the performance, but Willie was very much in command. His voice may have aged, but it’s aged like a fine whiskey—warm, smooth, and full of character.
Mickey Raphael delivered those signature harmonica lines that are as much a part of Willie’s sound as Trigger itself. There were several heartfelt nods to Willie’s musical family and heritage throughout the night, but none more poignant than the star-studded rendition of “Will the Circle Be Unbroken” and “I’ll Fly Away,” with The McCrary Sisters, Sheryl Crow, Chris and Morgane Stapleton, Nathaniel Rateliff & The Night Sweats, and Tami Neilson all gracing the stage. It was a true celebration of American music—one that paid tribute to the past while firmly planting its feet in the present.
If you ever have the chance to see the Outlaw Music Festival, don’t hesitate. And if it brings Willie and Bob together again, even better. I came for the legends—and I left with the firm belief that even in their twilight years, these icons still have plenty of fire left to give.
–Jerry Holthouse
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