On Friday, Phil Lesh and his “Friends” continued an extended nine-night October residency to celebrate Phil-o-Ween at The Capitol Theatre, a run of shows marking the Grateful Dead bassist’s 100th concert at The Cap since the venue reopened its doors in 2012.

The Capitol Theatre’s Phil-o-Ween shows are always filled with musicians who like to push boundaries and create a mind-bending, high-octane, psychedelic experience in the spirit of the Grateful Dead, and this weekend’s friends—Rick Mitarotonda (Goose), Grahame Lesh, John Medeski (Medeski Martin & Wood), John Molo (Moonalice), and the Trey Anastasio Band horn section of James Casey, Natalie Cressman, and Jennifer Hartswick—were primed to follow in that rich tradition. The personal significance of being selected as one of Phil’s Friends simply can’t be overstated, and Mr. Lesh was visibly pleased with his band, dancing and smiling with apparent delight as the evening unfolded.

Phil Lesh & Friends – “Here Comes Sunshine” – 10/21/22 [Pro-Shot]

Grahame Lesh would take the first vocal lead on “Here Comes Sunshine” before passing the baton to Rick Mitarotonda for a rousing “Tennessee Jed”, who in turn passed it back for an energetic “Big River”. While each was highly satisfying, there was a feeling out process underway in what was the band’s first time playing together in front of fans. Perhaps out of deference to the man with his name on the marquee, it seemed as if no one wanted to show all their cards too early, but that all changed in an instant when Jennifer Hartswick took the mic on “Dancing In The Streets”, thereby setting the bar to which all others would reach.

Phil Lesh & Friends – “Tennessee Jed” – 10/21/22

[Video: jackstrawfromwichita]

Jen’s powerhouse vocals broke the room open with smiles and dance before a buttery smooth transition into “Scarlet Begonias”, Goose’s Mitarotonda rising tall to Ms. Hartswick’s bar. The band would return without pause to “Dancing In The Streets”, Hartswick continuing to dazzle as she alternated between vocal and trumpet solos to complete a 20-minute “Dancing” > “Scarlet” > “Dancing” that left the crowd roaring with sustained appreciation. Regardless of whether one is familiar with the story of his journey or not, James Casey’s vocals encompass triumph, and that was the story as he took lead on a relatively compact “Fire On The Mountain” to close the first set.

Phil Lesh & Friends – “Ship Of Fools”, “Cassidy” – 10/21/22 [Pro-Shot]

“Ship Of Fools” (Rick) opened the second followed by “Cassidy” (Grahame/Natalie) before an uninterrupted hour of music would unfold as the band challenged one another to explore and push the boundaries of both sonic psychedelia and their relationships with one another. With the benefit of hindsight, it’s safe to say that lifelong friendships were made during the “St. Stephen” > “Dark Star” suite that followed.

Even the Grateful Dead only let Phil sing once a show (or less), but his vocals are iconic and we love him just the same. So when it’s his turn to sing, we all feel a little bit of nostalgia and comfort—and a whole lot of history—especially when that voice finds the words to “St. Stephen”. If you remember your Grateful Dead history, “St. Stephen” was put on the shelf on Halloween 1983, never to be played again as, according to Jerry Garcia, “We used it up.” That’s not the entire story, but it’s part of what made Phil’s vocals feel just right—even if they were a little wrong—as the band behind him really started to take shape and push the envelope.

John Medeski seemed to be the story of the second set and his organ play during “Stephen” set the tone the rest of the way as he pushed, poked, and prodded those around him to explore the best versions of themselves, not least of all dummer John Molo. Dare I say the Grateful Dead never had a keyboardist quite like Medeski, and watching him challenge the dual guitars of Mitarotonda and Lesh, it was fun to daydream about how he might have fit on stage with Garcia and Weir.

Long story short, it was quintessential Grateful Dead in modern form and the set went down like this: “St. Stephen” > “The Eleven” > “Dark Star” > “The Other One” > “Dark Star” > “Going Down The Road Feeling Bad” > “And We Bid You Goodnight”. Complex passages discovered through psychedelic explorations, culminating with a jubilant “GDTRFB” and an arm-in-arm singalong to “And We Bid You Goodnight”. After a short encore break, the band returned with “Brokedown Palace”, Mitarotonda stealing the show with powerful, heartfelt vocals that sent the crowd home in head-shaking awe.

Phil Lesh & Friends – “Brokedown Palace” – 10/21/22

[Video:Marc Komito]

After setting an admirably high bar for themselves on opening night, I still have to believe that the best is yet to come for Phil & this group of Friends, who return to The Cap tonight for the second of three consecutive nights.

Setlist: Phil Lesh & Friends | The Capitol Theatre | Port Chester NY | 10/21/22

Set One: Here Comes Sunshine, Tennesse Jed, Big River, Dancing In The Streets > Scarlet Begonias > Dancing In The Streets, Fire On The Mountain

Set Two: Ship Of Fools, Cassidy, St. Stephen > The Eleven > Dark Star > The Other One > Dark Star > Going Down The Road Feeling Bad > And We Bid You Goodnight

Encore: Phil Donor Rap, Brokedown Palace