90-year-old outlaw country icon Willie Nelson brought his touring Outlaw Music Festival to Forest Hills Stadium on Sunday to help New York music fans close out the late-summer weekend with a day full of eclectic sets and noteworthy collaborations by Willie Nelson & Family (featuring full-set special guest Norah Jones), Bob Weir & Wolf Bros featuring The WolfpackThe String Cheese IncidentLos Lobos, and Waylon Payne.

The familial atmosphere and collaborative spirit endured throughout the pleasant Sunday afternoon even as spurts of rain threatened to dampen the celebratory ambiance. Waylon Payne, the country singer-songwriter whose father was a longtime member of Willie Nelson’s band and whose mother toured as a singer with Waylon Jennings, for whom he is named, got the day’s programming started before Los Lobos injected some Latin flair into the folk-forward proceedings. Los Lobos’ Steve Berlin hung around after his band’s set to add some saxophone sounds to the brief but energetic set from The String Cheese Incident (on “Let’s Go Outside”) while Willie’s harmonica player, Mickey Raphael, lent his harp to a rendition of “MLT”.

Related: 30 Years In, The String Cheese Incident Isn’t Afraid To Ask For Help On ‘Lend Me A Hand’ [Interview]

Bob Weir, the singer/guitarist of Grateful Dead fame, was up next with his ever-evolving Wolf Bros/Wolfpack ensemble. While the Dead and the outlaw country greats like Nelson have often existed in separate realms, they’ve always shared a strand or two of DNA. Weir and the Dead have spent pockets of time exploring a unique take on a country music aesthetic, while Willie—with his proclivity for mind-altering greenery and counter-cultural leanings, both in music and action—shares a kinship with the spirit of the influential hippies from the Haight.

While Wolf Bros was initially launched as a stripped-down trio, Weir has been realizing the full potential of his Americana-oriented Grateful renderings with the band’s latest, ten-piece iteration, offering some of the most unique and immersive takes on the timeless songbook in the post-Garcia era. For his Outlaw Music Festival appearance in New York, Bobby had his full Wolf Bros/Wolf Pack complement on hand (aside from regular saxophonist Sheldon Brown, who was replaced by Weir veteran/former RatDog member Kenny Brooks).

Bob Weir Joins Willie Nelson At Outlaw Music Festival In South Carolina [Videos]

Wearing his Stetson with pride and grace, Weir guided the outfit with the grizzled presence of a Big Sky rancher as they moved through classics from the live Dead catalog like “Jack Straw”, “Ramble On Rose”, “Black-Throated Wind”, “Estimated Prophet”, “Standing On The Moon”, “Turn On Your Love Light”, and “Samson and Delilah”. He also reached beyond the Dead catalog for several memorable moments, from an early-set Wolf Bros cover debut of the Willie Nelson-adopted “Blue Eyes Crying In The Rain” (featuring Mickey Raphael on harmonica) to a standout “Eyes of the World” that moved gracefully into (and back out of) a cover of Marvin Gaye‘s “What’s Going On”. Bob Weir has worn many (figurative) hats in the years since the Grateful Dead scattered back in 1995, but with this latest version of the Wolf Bros experiment—sharing a stage with a country legend, no less—Bobby has found a “cowboy” hat (both literal and figurative) that suits him remarkably well.

The biggest surprise of the day came when Willie Nelson took the stage under sheets of rain for his headlining set with a familiar player behind the keys: lauded singer/pianist Norah Jones. Filling the seat vacated by Willie’s late sister and longtime piano player, Bobbie Nelson, who passed away in 2022, was surely an emotional task for Jones, but the self-proclaimed Willie superfan was more than equipped to handle the assignment. While she dutifully hung back for much of the show as “one of the band,” Nelson threw it to her on more than a few occasions, allowing her to show off her smoky vocal harmonies and ample abilities on 88 keys.

To close things out, Nelson opened the stage to the various artists who had played before him. Bob Weir, Waylon Payne, members of The String Cheese Incident, Jones’ Puss n Boots bandmate Sasha Dobson, and more for a set-closing run of “Will The Circle Be Unbroken?”, “I’ll Fly Away”, and “It’s Hard To Be Humble”.

Related: It’s Hard To Be Humble When You’re Willie Nelson In Central Park [Review/Videos]

Scroll down to check out a gallery of photos from Sunday’s Outlaw Music Festival stop at Forest Hills Stadium via photographer David Gray. Click below to view a selection of fan-shot videos from the day.

The 2023 Outlaw Music Festival tour continues on Wednesday, September 20th in Bridgeport, CT with Bob Weir & Wolf Bros ft. The Wolfpack and Waylon Payne. For a full list of the tour’s upcoming dates and artist lineups, head here. For ticketing information, head here.

Willie Nelson w/ Norah Jones – “Georgia On My Mind” (Hoagy Carmichael, Stuart Gorell) – 9/17/23
[Video: nyeddiem]

Willie Nelson w/ Norah Jones, Bob Weir, The String Cheese Incident, More – “I’ll Fly Away” (Partial) (Traditional) – 9/17/23


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Bob Weir & Wolf Bros ft. The Wolfpack – “Jack Straw” – 9/17/23
[Video: nyeddiem]

Bob Weir & Wolf Bros ft. The Wolfpack, Mickey Raphael – “Turn On Your Love Light” (Bobby “Blue” Bland) – 9/17/23
[Video: nyeddiem]

Bob Weir & Wolf Bros – “Blue Eyes Crying In The Rain” (Willie Nelson) –  9/17/23
[Video: nyeddiem]

Bob Weir & Wolf Bros ft. The Wolfpack – “What’s Going On” (Marvin Gaye) – 9/17/23

[Video: nyeddiem]

The String Cheese Incident – “Hi Ho No Show” – 9/17/23

[Video: nyeddiem]

Los Lobos – “La Bamba”/”Good Lovin'” – 9/17/23
[Video: Daniel Marino]

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