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Willie Nelson performs as part of his Outlaw Music Festival Friday night, Sept. 22, at the Pine Knob Music Theatre (Photo by Mike Ferdinande)
Gary Graff is a Detroit-based music journalist and author.
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A significant tinge of tie-dye gave Willie Nelson’s Outlaw Music Festival some additional psychedelic flavor on Friday night, Sept. 22, at the Pine Knob Music Theatre.

But that was certainly in keeping with the spirit of a traveling package that, as its title suggest, champions music, and music of a particular spirit, above genre or image.

While Nelson and opener Waylon Payne (son of longtime Nelson guitarist Jody Payne and a current member of Nelson’s band The Family) brought the country/Americana that’s Outlaw’s root, the Grateful Dead’s Bobby Weir and his Wolf Bros and String Cheese Incident contributed a “jam band” aesthetic, filling their respective sets with improvised instrumental excursions that were as pure as Nelson rolling through his array of standards. It may look like a collision on paper, but in the flesh on Friday — and partly owing to the acts’ tailoring their sets to the occasion — the co-existed seamlessly for the crowd 12,000-plus, the cowboy hats twirling along to the Dead’s “Ramble on Rose” and the hippies, old and young, singing along to Nelson’s “Mamas Don’t Let Your Babies Be Cowboys” and “On the Road Again.”

And in the ultimate display of playing nice together, Weir sat in with Nelson and The Family for the entirety of its hour-long set, while the String Cheese Incident joined towards the end for the spirituals couplet “Will the Circle Be Unbroken” and “I’ll Fly Away.”

Besides the music, Friday’s show was also part of the continuing celebration of Nelson’s 90th birthday back in April. (Weir even sported a T-shirt from special concerts for the occasion at the Hollywood Bowl). Nelson is at this point operating in the rarest of territories for a performing musician, and while it’s fair to say he’s no longer at the peak of his powers it was hard not to be awe-struck and marvel at how potent he remains both as a singer and a guitarist, still playing his beat-up acoustic Trigger with the nimble fluidity of a jazz cat. The greatest concession to his age — The Family stripped down to an acoustic quartet (plus Weir on Friday), using just a snare drum played with brushes — allowed Nelson to shine in a different way and become what he’s always been at his heart, a troubadour telling stories and singing songs that are indelibly part of the cultural tapestry.

Grateful Dead co-founder Bob Weir, right, sits in with Willie Nelson during the Outlaw Music Festival Friday night, Sept. 22, at the Pine Knob Music Theatre. Weir played earlier in the evening with his band, Wolf Bros. (Photo by Mike Ferdinande)
Grateful Dead co-founder Bob Weir, right, sits in with Willie Nelson during the Outlaw Music Festival Friday night, Sept. 22, at the Pine Knob Music Theatre. Weir played earlier in the evening with his band, Wolf Bros. (Photo by Mike Ferdinande)

It was an intimate occasion, in other words, and the head-banded, ponytailed (as always) Nelson — whose appreciation of his status could be seen in the warmth of his gaze into the crowd — worked his way smoothly through 23 songs over the course of his hour, saying little but communicating plenty from his traditional start with Johnny Bush’s “Whisky River” through his own hits and treatments of Bob Wills & His Texas Playboys’ “Stay a Little Longer,” Merle Haggard’s “Workin’ Man Blues,” “Billy Joe Shaver’s “I Been to Georgia on a Fast Train,” Hank Williams’ “Move It On Over” and a pair of Kris Kristofferson songs (“Help Me Make It Through the Night” and “Me and Bobby McGee”) that featured Payne.

The Pine Knob crowd, not surprisingly, was fully on board for “party songs” such as “Roll Me Up and Smoke Me When I Die” and “I Gotta Get Drunk,” as well the defiant “Still Not Dead” and “Write Your Own Songs,” the latter a middle finger, recorded with Kristofferson, towards the music industry. But there was also audible sighs and rapt attention for quieter favorites such as “Angel Flying Too Close to the Ground” and “Always on My Mind.”

As short as the set was it never felt rushed, as Nelson and company gave all of the songs their proper airing and even stretched out at various points. And it certainly left anyone there hoping for many, mostly likely happy, returns from Nelson as he continues his seemingly endless musical journey.

performer on stage
Oak Park native Don Was, a Grammy Award-winning record producer and president of Blue Note Records, performs with Bobby Weir & Wolf Bros during the Outlaw Music Festival Friday night, Sept. 22, at the Pine Knob Music Theatre. It was Was’ first-ever performance at Pine Knob. (Photo by Mike Ferdinande)

It was a winning night for Weir and Wolf Bros, too — even if the nearly 90 minutes on stage is less than half of the group’s usual time on stage. The quintet — including Oak Park native Don Was in his first-ever Pine Knob performance and the adjunct Wolf Pack of horn and string players — was nevertheless at its peak powers on Friday, weaving one song into another with plenty of space for musical dexterity from all concerned.

Following String Cheese Incident’s lively performance, Wolf Bros was more rootsy than psychedelic, even twangy on the Dead’s “Ramble on Rose,” a cover of Haggard’s “Mama Tried” and portions of “Weather Report Suite.” “Let It Grow” was the set’s epic, the musicians passing the proverbial ball between them and building to an ecstatic crescendo, while the Beatles’ trippy “Tomorrow Never Knows” was sandwiched between the Dead’s “Scarlet Begonias” and “Wharf Rat,” which seamlessly morphed into Chuck Berry’s “Around and Around.”

It was a microcosm of Weir’s broad grounding and of American music in general — and proof that these Outlaws were not such strange bedfellows after all.

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