Even after playing Grateful Dead music for 60 years, Bob Weir can still pull a surprise or two out from behind his Lorax mustache. On Sunday, the elder statesman of the jam scene reconvened the Dead Ahead Festival‘s titular marquee band for a three-set performance, including an unannounced trio set with Sturgill Simpson and Goose guitarist Rick Mitarotonda.

After playing its first of three nights in Cancún, Mexico on Friday, the all-star band of Bob Weir, Sturgill Simpson, Rick Mitarotonda, Don Was, and Weir’s Dead & Company bandmates Oteil Burbridge, Jeff Chimenti, and Jay Lane hit the beach again on Sunday night. Bobby opened the show by taking lead on “Shakedown Street” before spreading the love around with Rick taking control of “Friend of the Devil” next followed by the first surprise of the evening—Jay Lane taking over John Mayer‘s high falsetto in the vocal back-and-forth with Bobby on “Jack Straw”. The surprises notwithstanding, the obligatory Sunday “Samson and Delilah” could have been printed on the tickets and came as no shock when it arrived midway through the first set.

Despite the vast talent pool already onstage, the collective Dead Ahead band called up special guest Brandi Carlile because—let’s be honest—for all that fancy fretwork they still didn’t have a true singer. The country singer-songwriter, set to host her curated Girls Just Wanna Weekend 45 miles down the beach this coming weekend, started off her three-song sit-in by sharing lead vocals with Weir on “Bird Song” before Bobby handed over the reins for a beautifully dark “Loser”. Finally, the highlight of the set and one of the night’s top moments came as Carlile led the band through a moving tribute to late Grateful Dead bassist Phil Lesh on “Box of Rain”. By handing off the tribute to somebody outside the jam band enclave, Weir and company further underscored the Dead’s influence across genres and communities.

Dead Ahead, Brandi Carlile — “Box Of Rain” — 1/12/25

[Video: Steve Leitman]

After a short break, Weir and Simpson took the stage alone for a short singalong set. Bobby may have had the hat, but Sturgill had the voice to properly take on Weir’s time-honored cowboy tunes starting with Merle Haggard‘s “Mama Tried”. The campfire interlude continued with “Ripple”—which Simpson sang for the Dead at the band’s Kennedy Center Honors gala last year—before Mitarotonda reemerged to add tasteful electric guitar fills on “Me and My Uncle”. As the wind whipped across the Riviera Maya beach, it forced the audience into an awed hush so they could hear the near-a cappella “Deep Elem Blues” that closed the surprise middle set.

Returning to the full band configuration, “Deal” kicked off the final set of the evening ahead of “Scarlet Begonias”, which gave Simpson his first turn on lead vocals with the completed lineup. The reggae bounce of “Estimated Prophet” rode the waves of the adjacent Caribbean Sea and linked up with “Eyes of the World” for a 25-minute apex of improvisation. Though Sturgill took only a few runs at the band’s lyrical helm, he made the most of his opportunities as he turned the scorched Earth anthem “Morning Dew” into a climactic crescendo before Rick finished it off with “Cold Rain and Snow”. Back for the encore, everyone was reminded it was Bobby’s sand—they’re all just playing in it—as he closed the show with “Turn on Your Lovelight”.

Dead Ahead — “Morning Dew” (Bonnie Dobson) — 1/12/25

[Video: Steve Leitman]

Check out some videos from the Dead Ahead band’s second show in Mexico by Steve Leitman. The group returns tonight, January 13th, to finish the festival.

Dead Ahead — “Shakedown Street” — 1/12/25

Dead Ahead — “Friend Of The Devil” — 1/12/25

Dead Ahead — “Jack Straw” — 1/12/25

Dead Ahead — “Samson And Delilah” (Traditional) — 1/12/25

Dead Ahead, Brandi Carlile — “Bird Song”, “Loser” — 1/12/25

Bob Weir, Sturgill Simpson — “Mama Tried” (Merle Haggard) — 1/12/25

Bob Weir, Sturgill Simpson — “Ripple” — 1/12/25

Bob Weir, Sturgill Simpson, Rick Mitarotonda — “Me And My Uncle” (John Phillips) — 1/12/25

Bob Weir, Sturgill Simpson, Rick Mitarotonda — “Deep Elem Blues” (Traditional) — 1/12/25

Dead Ahead — “Deal” > “Scarlet Begonias” — 1/12/25

Dead Ahead — “Estimated Prophet” > “Eyes Of The World” — 1/12/25

Dead Ahead — “Cold Rain And Snow” (Traditional) — 1/12/25

Dead Ahead — “Turn On Your Lovelight” (Bobby “Blue” Bland) — 1/12/25

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Setlist: Dead Ahead | Dead Ahead Festival | Moon Palace Hotel | Cancún, Mexico | 1/12/25

Set One: Shakedown Street, Friend of the Devil [1], Jack Straw [2], Samson and Delilah (Traditional), Bird Song [3], Loser [3], Box of Rain [3]
Set Two: Mama Tried (Merle Haggard) [4], Ripple [4], Me and My Uncle (John Phillips) [5], Deep Elem Blues (Traditional) [5]
Set Three: Deal > Scarlet Begonias [6], Estimated Prophet > Eyes of the World, Morning Dew (Bonnie Dobson) [6], Cold Rain and Snow (Traditional) [1]
Encore: Turn on Your Lovelight (Bobby “Blue” Bland)

[1] Rick on lead vocals
[2] Jay Lane on lead vocals
[3] w/ Brandi Carlile
[4] Bob and Sturgill only
[5] Bob, Sturgill, Rick
[6] Sturgill on lead vocals