By Zachary Benjamin
I never met Bob Weir z”l, the iconic rhythm guitarist and reluctant latter-day face of the Grateful Dead, who passed away in January at age 78. However, his fingerprints have been indelibly imprinted on almost every phase and facet of my life.
My love affair with the Grateful Dead began somewhere around age 10, as an elementary school student in Southern California. Its seeds were sown on road trips with my dad, listening to missives from his college years in Iowa, during which he enjoyed a handful of chance encounters with the band’s indominable leader and legendary eccentric, Jerry Garcia.
I purchased my first item of Dead merchandise (a white t-shirt with “Grateful Dead” splashed in psychedelic yellow lettering across the chest) before I had ever heard a note of the group’s music. The teacher’s aide that year in Mrs. Squire’s sixth-grade classroom was a long-haired, kind Jewish Deadhead in his 30s who had chosen a career in education so that he could spend his summers on tour with the band, an annual journey of pilgrimage embraced by hundreds of thousands of the Dead’s faithful.
My parents bought me my first Grateful Dead album a year later, and like much pertaining to the Dead experience, the music itself proved to be an acquired taste. However, the mythology of the band, its legions of adherents, and the singular spirit of those I had encountered from the Deadhead community compelled me to keep listening. As a preteen neophyte, I had yet to develop any appreciation for the nuances of the music or the band’s defiant identity as an act tailor made for the live stage, rather than the recording studio.
Over time, I would develop a deep reverence for the music and its architects, including Weir, Garcia, and lyricists Robert Hunter and John Perry Barlow. The Dead’s catalogue weaves tapestries of poetry and song that are at once whimsical and relatable, comforting and compelling, humorous and heartbreaking. With eloquence and dry wit, these artists spun tales of rails and asphalt, of foibles and faux pas, imperfect crimes and love both requited and not.
Jerry Garcia died when I was 12-years-old, and it would be another eight years before I would finally develop the means and motivation to attend a live Dead performance.
On August 3, 2003, I convinced my then-roommate—who was mostly uninspired by the Dead, but who would, ironically, eventually oversee the band’s marketing catalogue for Rhino Records—to drive with me the 65 miles from Evanston to Joliet, Illinois, where the latest iteration of the band was to play at Route 66 Raceway. At that time, the group was still endeavoring to find and forge its identity in the post-Garcia era, and so the lineup was a mixed salad of original members and guests, including Bob Dylan, Joan Osbourne, Phish lead singer Trey Anastasio, and eventual full-time Dead keyboardist Jeff Chimenti. The one constant across the eras of the band’s evolution—from its genesis as a Palo Alto jug band in the early 1960s to a bluegrass-inspired rock juggernaut that elevated audiences for a full 60 years—was Bobby Weir. From my first attempts to appreciate the Dead’s music to his final concert last summer, Bobby’s soulful, mournful, mischievous voice resonated both musically and spiritually with me in a way more profound than that of any other artist.
My roommate and I left the show satisfied but still without a complete understanding of the movement and its ability to inspire so many millions of Deadheads. While he would drift back to his own musical preferences, I remained “on the bus,” as Deadheads colloquially refer to our fandom, and over the ensuing decades would become fully immersed in the magic of the Deadhead movement.
I have since lost track of how many shows I have attended over years and across the miles, although the number must be approaching 50 (modest by the standards of the Deadhead community, where it is not uncommon for fans to have attended more than 100 performances). My relationship with the Dead has evolved and matured with the band itself, as have my relationships with the many fellow Deadheads with whom I have developed deep and lasting friendships.
The Jerry Garcia era of the Grateful Dead lasted exactly 30 years, from 1965 to 1995, as did—coincidentally and serendipitously—the 1995-2025 Bobby Weir era. When Jerry passed, many Deadheads of the time hung up their traveling shoes and exited the bus, assuming that the movement and the band had run their respective courses. Bobby knew better. His mantra throughout his 62-year run as a sage of the rock-and-roll counterculture was, to paraphrase the song of the same name, that the music would never stop. Indeed, it has continued uninterrupted since those first notes were struck in Palo Alto on New Year’s Eve 1963, despite the band and its composite musicians changing and evolving, joining, passing away or moving on, and always inevitably yielding to a new generation or iteration.
The most recent incarnation of the Dead, “Dead and Company,” embodied this spirit of endurance and adaptability, as did its unlikely lead guitarist, the satin-throated crooner John Mayer, previously known more for his saccharine pop ballads and legions of teenage fans than for meaningful musicianship. Bobby Weir hand-picked Mayer as the next steward of both the music and the movement, a choice that we now know may well ensure that the music and community endure for another 30 years and beyond.
In 2023, I hit the road for six shows of the band’s final tour, spanning the continent from Los Angeles to Chicago, and from Boulder to San Francisco. I leaned into a scene that had been revived and re-energized by a new generation of Deadheads who, to my delight, had graduated from the “Mayer maniacs” to fully embrace, and indeed to profoundly enhance, the spirit of the Dead. My joyful journey continued through a handful of Dead and Company’s Las Vegas Sphere shows in 2024 and 2025 and culminated at their three-show Grateful Dead 60th-anniversary run in San Francisco’s Golden Gate Park last August.
Those three euphoric evenings in the park would prove to be Bobby Weir’s final live performances.
But Bobby, of course, knew exactly what he was doing when he brought John Mayer into the bosom of the band a decade earlier. He had identified in John both the skill and the ruach necessary to lead both the Dead and Deadheads into the next era of the Grateful Dead. By every measure, Mayer has met the moment and, in so doing, has affirmed both the genius and the mad methodology of Bob Weir in ensuring that the music truly never stops.
My identity has been shaped to a significant degree both by Judaism and by my membership in the global community of Deadheads. The music of the Dead provides a backdrop that so elegantly accompanies the Jewish values and themes of trial, challenge, perseverance, kindness, curiosity, and social action that have guided my own life and career. To be a Jewish Deadhead is to be part of two complementary, often overlapping cultures whose histories are in a perpetual state of authorship, and which have served to bring light and life to civilization.
Fare thee well, Bobby. May your memory be for an eternal blessing, and may the music never stop.