Willie Nelson’s Outlaw Festival Is A Mindblowing Showcase Of Country’s Past, Present And Future

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Is there a more beloved icon in America today than Willie Nelson? He’s like your cool, pot-smoking grandpa who’s as quick to bust out a tearjerker of song as he is to warm your heart with an infectious laugh. It’s the reason he remains the only 84-year old going who can continuously pack them in at 20,000 seat-plus outdoor amphitheaters in nearly every town in the country. This summer, some of Willie’s biggest fans and oldest friends have joined up with him once again for his Outlaw Music Festival, an OG Lollapalooza-type touring event. The tour features a shifting lineup of some of the most vital, and important country music artists in the game today seeking to one-up each other on a nightly basis.

I caught the show this last weekend at Summerfest in Milwaukee, Wisconsin. On the bill that evening was Lukas Nelson -– Willie’s son -– Margo Price, Nathaniel Rateliff, Jason Isbell, Sheryl Crow, Willie, and just before him, Bob freaking Dylan. The entire thing is a nine hour long continuous marathon of music that never really wears down. It was a perfectly paced mix of country music’s past, it’s present and a small glimpse into its future. While everyone on the bill brought their A-game, some folks burned just a little bit brighter than the others. Here’s a ranking of the best performances I saw.

Lukas Nelson

It’s no shot at Lukas Nelson that he finds himself at the bottom of this list. Like I said, the bill is completely stacked and someone had to be last. As both a guitar player and vocalist, Lukas is a force to be reckoned with. That was driven home much later during the show when he reappeared to back up his dad onstage and tore the roof off the joint with a jaw-dropping cover of “Texas Flood.” He’s got a new, self-titled album coming out next month on August 25th with his band the Promise of the Real and I’m very eager to check it out.

Margo Price

Margo Price’s debut Midwest Farmer’s Daughter was one of the best country albums released in 2016. It’s a thoughtful return to some of the most cherished sounds and themes of country music’s past, recorded in the venerated halls of Sun Studio in Memphis. Onstage, Price’s charming presence belies some of that album’s heavier, world-weary material, which suits me just fine. For instance, you can’t help but dance and sing to the generally cheery vibes of the set-ender “Hurtin’ (On The Bottle).” It’s only after the words, “I’ve been drinking whiskey like it’s water / But that don’t touch the pain you put on me,” come out of your smiling lips that you realize how truly dark it all is.

Nathaniel Rateliff

Full disclosure: I had no idea who Nathaniel Rateliff was until I saw him onstage on Sunday night. I’d never heard his name, nor had I listened to a single note of his music. I went into his set as cold as it gets and loved every single minute of it. Be it his relatively diminutive stature or the joyful horns that accented nearly every song he brought out, the entire thing reminded me of Van Morrison Caledonia Soul Orchestra period in the early 1970s that was so beautifully captured on the live album It’s Too Late To Stop Now. There’s hardly a higher compliment I could pay to an entertainer.

Willie Nelson

Here’s the thing about Willie Nelson, despite the fact that he’s getting on in years, the man remained one of the best pure guitar players to hit the stage across all nine hours of live entertainment. While his voice might be a little bit shaky these days — he compensates in that department by alternately leaning on either the crowd or his son Lukas to fill in here and there — when the time comes for a solo, he and his faithful Martin acoustic guitar “Trigger” deliver each and every time. It’s actually marvelous to watch.

As opposed to some other elder statesmen hitting the circuit these days, Willie doesn’t at all feel like a museum piece. His presence is so entirely joyful, right down to the way he tosses out signature red bandanas to the fans out in the front row. Needless to say, it’s an absolute thrill to belt out songs like “Mamas Don’t Let Your Baby’s Grow Up To Be Cowboys,” “On The Road Again,” or “Whisky River” along with the Red Headed Stranger. Do yourself a favor and see him while you still can.