7 takeaways from Willie Nelson's Outlaw Music Festival at Summerfest

Piet Levy
Milwaukee Journal Sentinel
View Comments

Summerfest will have just 10 amphitheater shows this year, after Ozzy Osbourne, and then his replacement Megadeth, both canceled due to health issues. 

But the Big Gig is actually offering more amp action than usual this year, thanks to Willie Nelson's Outlaw Music Festival, which stopped at the American Family Insurance Amphitheater Thursday, featuring seven superb acts across more than 10 hours.

Here were some of the day's highlights.

Willie Nelson plays the Outlaw Music Festival at the American Family Insurance Amphitheater on June 27, 2019.

Willie Nelson & Family 

Willie Nelson's guitar playing at first sounded like his battered acoustic guitar Trigger looked. 

But after the rough riding of opening number "Whiskey River," the 86-year-old legend found his groove with lush guitar runs, and hints of flamenco and jazz, coming out a toe-tapping "Shoeshine Man."

Nelson infused beautiful guitar licks across much of his hourlong closing set, matched by little sister Bobbie's swinging saloon piano and Mickey Raphael's sweet harmonica fills, and contrasted by Nelson's signature plain-spoken delivery. There have been shows when that flat, rushed delivery suggests he's not invested, but not Thursday, when tender eyes as he sang "Georgia On My Mind" and new song "Maybe I Should Have Been Listening" made these less like performances and more like confessionals. 

But Nelson was in a fine spirit for much of his set, bringing a playful spark to Mac Davis' "It's Hard to Be Humble," and tossing his cowboy hat like a frisbee into the audience, which hovered over the crowd for a second like a flying saucer, before falling into a lucky fan's hands. 

Phil Lesh & Friends perform at the Outlaw Music Festival at the American Family Insurance Amphitheater on June 27, 2019.

Phil Lesh & Friends 

The best part about Phil Lesh and Friends’ set wasn’t what they played, but how they played.

Lesh, the Grateful Dead’s founding bassist, and his five band mates relished showing off through twisting, turning Dead jams like “Shakedown Street” and “Operator.”

But the real fun of the show was seeing how enthralled they were with each other as the audience was of them. From North Mississippi Allstars’ Luther Dickinson jumping for joy during Jason Crosby’s organ purrs on “Black Peter,” to Lesh nodding with approval as the Friends played, sticking his tongue out Gene Simmons style at the end of a bluesy “Mississippi Half-Step Uptown Toodeloo,” the show felt more like a great hang than anything else.

The Avett Brothers perform at the Outlaw Music Festival at the American Family Insurance Amphitheater on June 27, 2019.

The Avett Brothers 

In the first three minutes, the Avetts went from foot-stomping bluegrass to soft piano ballad to speaker-blasting arena rock.

Fans wouldn't have it any other way.

Americana, however, remains the core, guiding their take of Randy Travis' "Forever and Ever, Amen" with Nelson's harmonica player Mickey Raphael, and a hushed "Just a Closer Walk With Thee" featuring just Seth and Scott Avett, and bassist Bob Crawford, huddled around a single mic.

They also previewed what could be the first single from a new album out in October, "High Steppin'," a quirky rocker with a midpoint sermon from Seth, who quipped it'd be a top 10 single on MTV. 

If "Old Town Road" can become a phenomenon, I suppose anything is possible. 

Counting Crows performs at the Outlaw Music Festival at the American Family Insurance Amphitheater on June 27, 2019.

Counting Crows 

Counting Crows was doing a fair job commanding the stage, but around 5:30 p.m., the band played second fiddle to a dark, menacing cloud that rolled across what had been beautiful blue skies. 

People on the bleachers and hilltop came running down under the roof, and hundreds of people hanging in the courtyards starting flowing in. Even Crows singer Adam Duritz, looking blankly over the horizon, seemed temporarily perplexed by what he was seeing. But suddenly playing for more than twice as many people, he had extra motivation to really ham it up for “Round Here.”

Alison Krauss performs at the Outlaw Music Festival at the American Family Insurance Amphitheater on June 27, 2019.

Alison Krauss 

No disrespect to Mr. Lesh, Counting Crows or the Brothers Avett, but wouldn't you think Alison Krauss — the most decorated woman in Grammy history — deserves one of the last set times on a festival bill? Perhaps Krauss wanted to start at 3:15 p.m. on a Thursday, but it's a shame more people weren't around to see her haunting and heartbreaking "Ghost in This House," in which she likens herself to a shadow on a wall after the death of her soulmate, or Krauss and the band's firecracker bluegrass swing through "Sawing on the Strings."

Beaming couples slow-danced near the stage for a radiant "When You Say Nothing at All," and Krauss' heavenly voice fluttered above James Mitchell's tender blues guitar for a cover of Nelson's "Angel Flying Too Close to the Ground." By the time Krauss' gentle voice floated through the amphitheater, musicians singing softly by her side, for the spiritual "It Is Well With My Soul," it was clear one of the first sets at Outlaw Thursday was the most magnificent. 

Dawes plays the Outlaw Music Festival at the American Family Insurance Amphitheater on June 27, 2019.


The amphitheater was even emptier when Dawes took the stage at 2 p.m. But the way the band played "When My Times Comes," with Taylor Goldsmith crooning beautifully with church-ready vocals and neck vein-bulging intensity, it felt like the place was packed. The growing crowd was equally enthralled by Goldsmith's Springsteen-esque lyrics, especially all the rich details, and even richer emotional context, for "A Little Bit of Everything." And before the set was over, there was one very special person in the crowd: Phil Lesh, who hung out in front of the sound board, grinning gleefully and bopping his head, and happily shaking hands and posing for pictures with fans who strolled on by.

Milwaukee singer-songwriter Trapper Schoepp kicks off the Outlaw Music Festival at the American Family Insurance Amphitheater on June 27, 2019.

Trapper Schoepp 

Milwaukee’s own Schoepp got to kick the whole thing off, playing a lovely ode to his home state, “On, Wisconsin,” that was partially written by Bob Dylan about 60 years ago. It’s from this year’s “Primetime Illusion,” which features another set-list highlight, “What You Do to Her,” a protest song against toxic masculinity. If only more male musicians, and more men period, would echo what Schoepp is saying.

RELATED:Summerfest 2019: Lizzo, Steve Earle, St. Paul and the Broken Bones, and the best and worst of a stormy Day 2

RELATED:The music returns to Summerfest after thunderstorm (temporarily) steals the show

RELATED:Summerfest 2019: Checking out 7 new things to experience (and eat) at the Big Gig

RELATED:Plan out your Summerfest 2019 with our interactive schedule

A previous version of this review incorrectly stated Willie Nelson's age. He is 86.

Contact Piet at (414) 223-5162 or Follow him on Twitter at @pietlevy or Facebook at

Piet also talks concerts, local music and more on "TAP'd In" with Jordan Lee. Hear it at 8 a.m. Thursdays on WYMS-FM (88.9), or wherever you get your podcasts.

View Comments