Simon & Garfunkel and The Grateful Dead were among the biggest music acts to emerge from the 1960s, although the New York folk-rock duo and the San Francisco jam band came from different parts of the musical spectrum.
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While the members of both acts rarely if ever collaborated in the studio, Simon & Garfunkel and The Grateful Dead did both play at the famed 1967 Monterey Pop Festival in Monterey, California, albeit on different days.
Long after the Grateful Dead broke up in 1995 following Jerry Garcia’s death, Paul Simon and Dead singer/guitarist Bob Weir finally performed together. The collaboration occurred at the 2019 Outside Lands festival on the Grateful Dead’s home turf, San Francisco’s Golden Gate Park.
Simon headlined the event on Sunday, August 11, 2019, and welcomed Weir as a surprise guest during his set’s encore. Before introducing Bob, Paul recalled the first time the two met.
“Well, I have an old friend who’s come out to join me tonight,” Simon told the crowd. “I met him in 1967, I had come up to [San Francisco’s] Haight-Ashbury [neighborhood] to invite The Grateful Dead to join the Monterey Pop Festival. I knocked on the door of their house, and Bob Weir opened the door, and we’ve been friends ever since. But actually, this is our first duet!”
Weir then walked on stage and joined Simon and his band for a rendition of Simon & Garfunkel’s classic 1969 ballad “The Boxer.” Bob played acoustic guitar alongside Paul, and added harmonies to the song’s “lie-la-lie” chorus section. After the performance, Weir and Simon embraced and took a bow with Paul’s band as the crowd cheered wildly.
Bob died on January 10, 2026, at age 78.
Songfacts: The Boxer | Simon & Garfunkel
In his 1984 Playboy interview, Paul Simon revealed that he wrote this song when critics were writing harsh things about his music – he was “the boxer.” Said Simon: “I think the song was about me: everybody’s beating me up, and I’m telling you now I’m going to go away if you don’t stop. By that time we had encountered our first criticism. For the first few years, it was just pure praise. It took two or three years for people to realize that we weren’t strange creatures that emerged from England but just two guys from Queens who used to sing rock ‘n’ roll. And maybe we weren’t real folkies at all! Maybe we weren’t even hippies!” (thanks, Tristan – L.A., CA)
The Grateful Dead Covered “The Boxer” Once in Concert
During The Grateful Dead’s long history, the band covered “The Boxer” one time in concert. On December 12, 1981, the Dead performed the song with folk legend Joan Baez at a show in San Mateo, California.
Simon & Garfunkel released “The Boxer” as a single in March 1969. The song reached No. 7 on the Billboard Hot 100 chart. It later was included on the duo’s final studio album, the chart-topping Bridge Over Troubled Water, released in January 1970.
Paul Simon’s Upcoming Performance Plans and Other News
Simon has announced plans for a spring 2026 European leg of his A Quiet Celebration Tour. The outing kicks off April 9 in Prague and is plotted out through a May 20 concert in Dublin. The trek will feature multiple performances in most cities it visits.
Paul launched his A Quiet Celebration Tour in 2025 with a series of concerts in the United States and Canada.
The shows included a full performance of Simon’s latest album, Seven Psalms, which was released in 2023. They also featured renditions of songs from throughout Paul’s long music career, including hits and deep cuts from various solo releases and several Simon & Garfunkel classics.
Simon’s wife, singer Edie Brickell, also performed several tunes with her husband at each show. Check out all the tour dates at PaulSimon.com.
Meanwhile, this Saturday, January 31, Simon will receive a Lifetime Achievement Award at the Recording Academy’s 2026 Special Merit Awards Ceremony. The event, which takes place a day before the 2026 Grammy Awards, will be held at the Wilshire Ebell Theatre in Los Angeles.
This year’s other Lifetime Achievement Award winners include Carlos Santana, Cher, Chaka Khan, the late Whitney Houston, and the late Afrobeat pioneer Fela Kuti.
(Photo by Gary Miller/Getty Images; Photo by Kimberly White/Getty Images)
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