Willie Nelson’s Outlaw Music Festival, Hollywood Casino Amphitheatre

By Daniel Durchholz

One of the best things about lineup-shifting, multi-band bills like the Outlaw Music Festival, which played Hollywood Casino Amphitheatre on Saturday, is that it makes possible collaborations between artists you’d otherwise probably never see together.

Musicians sat in with other bands on several occasions throughout the 9½-hour concert, but the best one occurred midway through Phil Lesh & Friends’ set, when Alison Krauss lent her crystalline soprano voice and violin to the Grateful Dead classic “To Lay Me Down.”

Krauss returned later to sing another Dead-related song, “Morning Dew.”

Lesh & Friends’ performance was all Dead-related, of course, and the five-piece band hit a number of cosmic, jammy highlights on its own during “Sugaree,” “Slipknot!” and “Cumberland Blues.” But the addition of Krauss took the songs to another dimension entirely.

That was especially encouraging to see because Krauss’ own set, which preceded Lesh & Friends, was a bit of a dud. Not the performance itself, which had a set list and stage design similar to her 2017 Stifel Theatre concert.

But the sublime vocals of Krauss on “River in the Rain,” “Stay” and “Baby, Now That I’ve Found You” were mostly lost on an audience that had come to party. The dull roar of conversations — probably equally dull — often drowned out the music.

Krauss fared better with the crowd on the up-tempo tunes “Let Your Loss Be Your Lesson” and “It’s Goodbye and So Long to You.” She earned cheers when she covered “I Never Cared for You” and “Angel Flying Too Close to the Ground” by festival anchor Willie Nelson. The response was also enthusiastic for “Didn’t Leave Nobody but the Baby” and “Down to the River to Pray” from the popular “O Brother Where Art Thou?” soundtrack.

The set’s big finish — covers of John Hartford’s “Gentle on My Mind” and Keith Whitley’s “When You Say Nothing at All,” plus the rousing gospel number “When I’ve Done the Best I Can, I Want My Crown” received a standing ovation, but it seemed mostly perfunctory. By the time that Krauss and her band attempted an a cappella encore of “It Is Well With My Soul,” the audience had turned its attention to other things and was filing out.

Meanwhile, headliner Willie Nelson — who was really the only legitimate “outlaw” on the bill — just keeps rolling on, even at age 86.

Like Krauss, Nelson didn’t vary his performance much from his previous St. Louis concert, a 2018 show at the Stifel. But as always, his songs come pouring out at such a torrid pace — 21 tunes in an hourlong set — it’s fun just trying to keep up.

Nelson dedicated songs to his late friends Waylon Jennings (“Good Hearted Woman”) and Merle Haggard (“It’s All Going to Pot”) and played a trio of tunes from the Hank Williams catalog (“Jambalaya,” “Hey Good Lookin’” and “Move It on Over.”)

He was having a good night vocally and on guitar. He performed some astonishing tricks on his guitar, “Trigger,” which is so beat up it almost hurts to see it in close-up on the video screens. But it still sounds great when Nelson reels off one of his jazzy, all-over-the-beat solos, or performs a lovely instrumental like Django Reinhardt’s “Nuages.”

Nelson visited some of his classics, including “Whiskey River,” “On the Road Again” and “Always on My Mind,” but some of his best offerings were from his just-released 69th (!) album, “Ride Me Back Home.”

Nelson doesn’t always plug his new albums in concert, but this one is worth it, notably for his takes on Guy Clark’s “My Favorite Picture of You,” Buzz Rabin’s (via Gene Watson) “Maybe I Should Have Been Listening” and Mac Davis’ comic “It’s Hard to Be Humble.”

A long day of music wrapped up with Nelson’s standard closing gospel medley of “Will the Circle Be Unbroken?” and “I’ll Fly Away,” which found Lesh and his bandmates joining in. But the legendary singer and irrepressible pot advocate added one more: “Roll Me Up and Smoke Me When I Die.”

The song would serve as a suitable epitaph for Nelson. But not anytime soon, please.

Old Crow Medicine Show, Dawes, and Shooting With Annie performed earlier in the day.

Willie Nelson setlist:

“Whiskey River”

“Still Is Still Moving to Me”

“Beer for My Horses”

“A Good Hearted Woman”

“Down Yonder”

“If You’ve Got the Money, I’ve Got the Time”

“It’s All Going to Pot”


“On the Road Again”

“Always on My Mind”

“Jambalaya (On the Bayou)”

“Hey, Good Lookin’”

“Move It On Over”


“Georgia on a Fast Train”

“My Favorite Picture of You”

“Maybe I Should Have Been Listening”

“It’s Hard to Be Humble”

“Will the Circle Be Unbroken?”/“I’ll Fly Away”

“Roll Me Up and Smoke Me When I Die”

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