Bob Weir started his Mexican vacation a little early this week, making a surprise appearance with Wynonna Judd in Cancún. The show came as part of Brandi Carlile‘s Girls Just Wanna Weekend destination event, held at the Hard Rock Hotel Riviera Maya, not far from where Dead & Company hosts its Playing In The Sand event.

Weir and Judd’s history stretches back to 1984 when the Grateful Dead singer/guitarist assisted on The Judds‘ “Why Not Me”. They have remained collaborators, exchanging the occasional sit-in and even releasing a joint studio recording of “Ramble On Rose” back in February 2020. That same month, Wynonna visited Weir’s home turf for a performance at The Fillmore in San Francisco where Bobby joined in for a number of Dead classics.

“Why Not Me” kicked off the collaboration on Tuesday in Mexico, with host Brandi Carlile joining in as well. The extended ensemble stuck together for performances of “Cry Myself to Sleep” and “The Other Side”, before concluding the sit-in with a pairing of “I Had a Dream” and “What It Takes”.

In addition to hosting, performing two nights (including a Brandi Carlile & Friends set), and sitting in with Judd, Carlile also made an appearance during Sara Bareilles‘ set on Wednesday. On what was scheduled as Carlile’s night off, the six-time Grammy winner (who is up for Best Americana Performance this year) joined Bareilles and Lucius for a run through Joni Mitchell‘s “California”. Carlile is one of Mitchell’s biggest contemporary advocates, helping organize the iconic singer-songwriter’s first ticketed concert in over 20 years, set for June 10th at The Gorge.  Brandi also helped Bareilles close her set with “She Used To Be Mine”, taken from Sara’s score for the 2015 musical adaptation of Waitress.

Relive Bob Weir and Brandi Carlile’s sit-ins from Girls Just Wanna Weekend with fan-shot videos below.

Wynonna Judd, Bob Weir, Brandi Carlile – “Why Not Me” – 1/10/23

[Video: Stephanie Hicks Horns]

Wynonna Judd, Bob Weir, Brandi Carlile – “The Other Side” – 1/10/23

[Video: Stephanie Hicks Horns]

Sara Bareilles, Brandi Carlile, Lucius – “California” (Joni Mitchell) – 1/10/23

[Video: Myers Boicurt]

Sara Bareilles, Brandi Carlile – “She Used To Be Mine” – 1/10/23

[Video: Myers Boicurt]