Best of the micro-fest: Ranking the seven Outlaw Music Festival performances
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Ah yes, the Outlaw Music Festival. Because what better way to decompress from the full-volume excess of Steve Aoki's opening day EDM show than 10 hours of live music.
As it turns out, actually, yes, there may not be a better way. Making its second stop headlining the American Family Insurance Amphitheater in three years, the Outlaw Music Festival is a festival inside of the festival, but without all the chaos and overwhelming, ADD-inducing extravagance of the latter. You're away from the herding crowds and competing musical acts, getting to simply sit and calmly watch the full variety of the entire country genre play out before your eyes like a lazy river trip through history. In fact, it's almost serene; where else could you hear birds chirping on a day at Summerfest?
Back in 2017, for the mini-festival's first visit, Willie Nelson served as the main headliner; two years later, he's returned but with an entirely new lineup preceding him. Sheryl Crow was replaced by Counting Crows, while playing the role of Margo Price was Alison Krauss.
Occupying Bob Dylan's spot as Nelson's fellow music legend on the tour was Phil Lesh and Friends. Jason Isbell and Nathaniel Rateliff turned into The Avett Brothers and Dawes. And in the well-connected opener slot, Willie Nelson's son Lukas and his band, Promise of the Real, was traded out for Milwaukee's son Trapper Schoepp.
But while the names and the songs changed, the experience was still the same: all-around excellent, a filling and satisfying day of music, with each band finding new ways to play in the same genre sandbox.
But which Outlaw Music Festival act aced Thursday's stop and made the biggest impact across the 10-hour musical marathon? Here's how I ranked Thursday's performances – though honestly, it's pretty much a seven-band tie for first place, less a worst-to-first ranking and more ranging from the best to the most best. No one should go away feeling bad – least of all those in the audience who got to see it all in one day under one roof. (And considering the storm that rolled in, god bless that roof.)
7. Counting Crows
When the 2019 lineup was first announced, my first reaction to seeing Counting Crows' name on the list was "Huh, that's a choice." The band's brand of rock music didn't quite seem to gel with the rest of the lineup, and frankly, I didn't even know Counting Crows was still performing together after its '90s/2000s heyday. (Remember: That's the Oscar-nominated Counting Crows to you.)
After now officially seeing the band's set, however, I can officially confirm that, indeed, huh, that was a choice.
Playing about an hour-long set ranging from the group's top 40 hits like "Mr. Jones," "Round Here" and "Hanginaround," plus a few deeper cuts, Counting Crows was by no means bad. Adam Duritz and company just stuck out a bit oddly from the rest of the pack – not really close to country and maybe just a passing resemblance to folk – and coming off the tight harmonies and luscious mixes of the two previous acts (Dawes and Alison Krauss) did their muddy sound mix, especially the muffled vocals, no favors.
Duritz's ambling conversational style makes for a compelling performance, and the hits still easily got the amiable crowd on its feet. But it was one of the few shows I could've done less of rather than more – though as the storm rolling across the sky during their set indicated, you could've made far worse, and wetter, decisions for your Thursday Big Gig matinee.
6. Trapper Schoepp
This is absolutely nothing against Milwaukee's Trapper Schoepp, who played one of his signature personable sets complete with lovely soaring sounds and pleasant, thoughtful and richly detailed Midwestern storytelling. There's only so much one can do with just 30 minutes in a 1 p.m. opening slot to a crowd barely scattered about the Amp. Plus, he's the only act here you could see for free at plenty of other local music festivals this summer. Still, at the end of his warm set, capped by "Ogallala" and an ode to the East Side, he received an equally warm ovation that sounded like it came from an audience double its actual size.
5. Phil Lesh and Friends
Phil Lesh and Friends definitely give the audience their money's worth – especially if they pay by the song. The second-to-last act of the Outlaw Music Festival only played seven numbers, but led by the Grateful Dead founding member and bassist, they stretched those few tunes into well over an hour of soaring music and warm vibes – very welcome as the humid summer afternoon weather weaned away into a brisk evening under the raised Amp roof. The first song, "Uncle John's Band," quickly cemented that sunny atmosphere, bringing shaggy fun to the stage and into the tie-dye-decked crowd.
Each song had its own tone – the bluesy vibe of "Loser" or "Black Peter"; the funky strut of "Shakedown Street" – but admittedly as the set went on and the songs grew in length, the sound threatened to meld together and become a bit monotonous. Part of this might be its place in the show, coming in seven hours deep into the day and reaching the point of exhaustion. But part of it is just purely preference.
There's no denying Lesh and company's excellent musicianship and just plain enduring power per song, nor is there any denying the crowd gathered in their Grateful Dead best happily soaked it all in. Plus, while the gaps between songs were filled with awkward silences and minimal crowd interaction, Lesh and company were clearly having a great time – and that was contagious. In all, a good, strong showing with great riffs – just not entirely my jam.
4. The Avett Brothers
Seth and Scott Avett got haircuts and shaved – last place, zero stars.
Jokes aside, once I adjusted to Seth looking a whole lot like Adam Scott from "Big Little Lies" and "Parks and Rec," they were still the lovable folksy rock band I knew and loved, putting a charge into a live crowd with a jamboree-like energy. There were a few non-hair-related hangups – a little of the brothers' tendency toward spoken word breakdowns and rap interludes (see the upcoming single "High Steppin" and the Jason Mraz-ian "Ain't No Man") goes a long way, and the vocals on the delicate "I Wish I Was" were almost too delicate to be heard – but when the North Carolina troupe is on, there are few live acts better.
From the plucky ruckus on covers like "Black Mountain Rag" and "The Race Is On," to the big anthemic triumph of "Head Full of Doubt/Road Full of Promise" and the bouncy, beautiful harmonies of "Live and Die" and "Satan Pulls the Strings," (very literally bouncy in lead singer Seth's case, who charmingly struts in place constantly as if he's trying to cheat his way to hitting his Fitbit step goal for the day), The Avett Brothers put on quite the show.
Amusingly enough, the MVP track of their set wasn't even one of their own: Instead it was a cover of Randy Travis' "Forever and Ever, Amen," fully weaponizing the band's silky harmonies and lovely charm.
Trapper Schoepp may have started the day at the Amp, but – no offense intended – it was the second act, Dawes, that truly got the Outlaw Music Festival going. Playing a 45-minute set of Western-tinged rock best played echoing down a long highway, the Los Angeles band hit the growing crowd with a wall of warm Americana storytelling that filled the Amp and would've made Tom Petty proud.
But while the band's arrangements and lush, Southern-fried harmonies sounded great, the star of the set was lead singer Taylor Goldsmith's lyrics, waxing mesmerizingly poetic about the stories of struggle and success. "A Little Bit of Everything," in particular, seemed to hush the crowd into rapt attention with its tales of mosaic of everyday life.
For their final number, Goldsmith and company sang of hoping "all your favorite bands stay together." Anyone witnessing the set had to hope to the same for Dawes – and that, on their next Milwaukee stop, they'll play longer than an all-too-quick 45 minutes.
2. Alison Krauss
First of all, bonus points to Krauss for bringing her own set. While almost everyone else was content to play in front of the standard Outlaw Music Festival signage (Willie Nelson was the only other exception, playing in front of – what else – a giant Texas flag) Krauss and her band performed in front of a mock backstage, a fake brick wall complete with glowing windows and vaudeville posters.
The extra effort was appreciated, but Krauss didn't need the backdrop to transport the Amp audience Thursday afternoon, turning the cavernous space into an intimate blues hall or honkytonk with merely her soulful, sweetly youthful voice and tender lyrics. Her harmonies with her bandmates were buttery smooth, with just that fun twist of twang mixed into the notes – and any time you thought you'd heard all Krauss had to offer, she played a curveball, like the haunted Southern bayou tune "Sister Rosetta Goes Before Us" that sounded delectably eerie (call it "Phantom of the Opry") or her two a cappella spirituals from "O Brother Where Art Thou."
By the end, after almost being moved to tears a few times by the luscious harmonies and heart-rending delicate lyrics, I knew I'd been transported – whether to a honkytonk back alley or to merely the midst of a sweet, soothing summer rain. No set dressing necessary.
1. Willie Nelson
After nine exhaustive hours tucked away under the newly raised Amp roof, I was beginning to wonder if seeing Willie Nelson would be worth the late night. I'd already seen him, after all, two years before, and I couldn't imagine him mixing things up too much. What would I really miss?
Well, I would've missed the best show of the night, an utter charmer of a set that blazed through country history and beloved icons – playing a bit of Hank Williams here, some Merle Haggard there, a splash of Waylon Jennings of course too – with the energy and momentum of a locomotive.
After shaking off the rust on his opener, "Whiskey River," Nelson trucked away song after song, calling out to the crowd on his most popular lyrics – and charmingly smiling after each response, as if it was the first time he'd heard them chimed back at him – and ably plucking away at his beat-up guitar way too well for a guy 25 years older than two of the United States.
You don't expect a 86-year-old to electrify a crowd to life at 10:15 p.m. on a work night after almost half a day of marathoning music, but that's exactly what happened Thursday night.
As an added bonus, in addition to his regular standby hits, Nelson played a few newer songs of his new record – the Guy Clark cover "My Favorite Picture of You" and "Maybe I Should Have Been Listening When You Said Goodbye" – that seemed to tap a little deeper into Nelson's soul. You can tell Nelson's played several of the songs on his setlist thousands of times into routine – though he doesn't look tired of them and neither does the crowd – while these tunes brought out a little extra oomph in his singing voice, like he was feeling them like new.
After bringing out some of The Avett Brothers for country classics "Will the Circle be Unbroken?" and "I'll Fly Over," Nelson wrapped up the night with "It's All Going to Pot" followed by the playfully dark notes of "Roll Me Up and Smoke Me When I Die" and "Still Not Dead." And considering the effortlessly charismatic way he performed Thursday night and brought a long day to a perfect close – not to mention the way he chucked his bandanas into the crowd afterward – the latter tune should stay true for a long time.
"Whiskey River" (Johnny Bush cover)
"Still Is Still Moving To Me"
"Beer for My Horses" (Toby Keith cover)
"Good Hearted Woman"
"If You've Got the Money I've Got the Time" (Lefty Frizzell cover)
"Shoeshine Man" (Tom T. Hall cover)
"On the Road Again"
"Always on My Mind"
"Jambalaya (On the Bayou)" (Hank Williams cover)
"Hey Good Lookin'" (Hank Williams cover)
"Move It On Over" (Hank Williams cover)
"My Favorite Picture of You" (Guy Clark cover)
"Maybe I Should Have Been Listening When You Said Goodbye"
"It's Hard to Be Humble"
"Will The Circle Be Unbroken?"
"I'll Fly Away" (Albert E. Brumley cover)
"It's All Going to Pot"
"Roll Me Up and Smoke Me When I Die"
"Still Not Dead"
Phil Lesh and Friends
"Uncle John's Band" (Grateful Dead cover)
"Loser" (Jerry Garcia cover)
"Scarlet Begonias" (Grateful Dead cover)
"Operator" (Grateful Dead cover)
"Shakedown Street" (Grateful Dead cover)
"Black Peter" (Grateful Dead cover)
"Mississippi Half-Step Uptown Toodeloo" (Grateful Dead cover)
The Avett Brothers
"Black Mountain Rag" (traditional)
"Satan Pulls the String"
"Live and Die"
"Forever and Ever, Amen" (Randy Travis cover)
"The Race Is On" (George Jones cover)
"Head Full of Doubt/Road Full of Promise"
"I Wish I Was"
"Just a Closer Walk With Three" (traditional)
"Ain't No Man"
"Slight Figure of Speech"
"No Hard Feelings"
"Mrs. Potter's Lullaby"
"Angels of the Silences"
"A Long December"
"I Never Cared For You" (Willie Nelson cover)
"Forget About It"
"Baby Now That I've Found You"
"Ghost in This House"
"Let Your Loss Be Your Lesson"
"The Lucky One"
"Sister Rosetta Goes Before Us"
"It's Goodbye and So Long To You"
"Angel Flying Too Close To the Ground"
"Go to Sleep You Little Baby"
"Let Me Touch You for Awhile"
"Sawing on the Strings"
"Down to the River to Pray" (traditional)
"Gentle on My Mind"
"When You Say Nothing At All"
"When I've Done the Best I Can, I Want My Crown"
"It Is Well With My Soul" (Philip Paul Bliss cover)
"Feed the Fire"
"Time Spent in Los Angeles"
"When My Time Comes"
"A Little Bit of Everything"
"All Your Favorite Bands"
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