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

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.

Sheryl Crow

Sheryl Crow has sold something in the neighborhood of 50 million albums worldwide. She has more classic songs than she knows what to do with at this point, including three different top-10 hits, so imagine my surprise when I come back from getting a beer and see her walking out with her band as the fourth artist on the bill. Fourth! The woman who wrote “Redemption Day” was going on before the sun even set. Not that she seemed to care one bit, because she owned that stage like a damn headliner, shiny silver pants and all. She sang, she danced, she hammed it up for the video cameras and audience up front. She hopped from instrument to instrument, at different times playing bass, piano, harmonica and guitar. She also got some of the biggest cheers of the night by busting out immortal hits like “Everyday Is A Winding Road,” “My Favorite Mistake,” and “If It Makes You Happy.”

Bob Dylan

Seeing Bob Dylan perform live is like going to visit the Statue of Liberty. Both are tremendous American icons, capable of inspiring awe, and reaffirming your belief in the better angels of our collective nature. Bob remains a mercurial performer. You can’t anticipate at all what he’s going to do onstage, or the way he’s going to do it. For his appearance in Milwaukee, Mr. Zimmerman put together a set that blended some of his greatest personal compositions alongside an array of standard classics from the ’40s and ’50s. While performing his own material, songs like “Desolation Row,” “Don’t Think Twice It’s Alright,” and “Highway 61” he either sat or stood in front of a gleaming baby grand piano, gruffly stringing together the words and directing his band with a head nod here, or a hand signal there.

For the Sinatra stuff, he took center stage, looking resplendent in an all-white jacket, crooning away to his heart’s content. Some might find his choice to delve into this particular oeuvre a little bewildering, but it really suits his modern, weathered voice. For his part, he just really seems to delight in singing it, especially “Melancholy Mood.” The set ended with the excoriating “Ballad Of A Thin Man” — my personal favorite — after which Dylan joined his band near the front to bask in the applause of the crowd. He leaned back, put his hands on his hips and let the affections of 20,000 people wash over him. Then he nodded approvingly and walked out, shrouded in darkness.

Jason Isbell

The most exhilarating performance of the Outlaw Festival, at least on the day that I attended, was delivered by Jason Isbell. Bob and Willie and Sheryl might have more widely recognized hits to their name, and a deeper catalog of material from which to draw from, but no one commanded the stage with greater authority than Isbell. The Alabama singer is currently on the road supporting what might the greatest album of his entire career, Nashville Sound and across his hour-long set he managed to play nearly ever single one its songs. From the dynamic “Anxiety” which he used to open with, to the hushed, almost Elliott Smith-tinged “If We Were Vampires” the wide spectrum of sounds and emotions he infused into his music was incredible to witness in-person.

When he did go back to the well, it was to stunning effect, no more so than on the Southeastern standout “Cover Me Up,” a love song he wrote for his wife Amanda Shires, which he sang while standing just a few feet away from her while she added some truly touching fiddle accompaniment. At the end of his set, he eschewed his own material and brought the house down with a volcanic cover of the Allman Brothers classic “Whipping Post.” The intensity was bewildering. The guitar acrobatics electrifying. Somewhere, I believe, both Duane and Gregg were looking down with approving smiles.