Ever since the name John Mayer began floating around Grateful Dead conversations in the nascent days of Dead & Company, fans have riffed on versions of the same joke: So, the “Wonderland” guy is Jerry now? When will Dead & Co bust out a heady “Your Body Is A Wonderland” jam? When will I get that “Help” > “Slip” > “Wonderland” I’ve been chasing? If Bob Weir sings it, we could call it “Your Bobby Is A Wonderland”. Dead & Co fans have even been known to slip “Your Body Is A Wonderland” into the setlists on the open-source setlist.fm during shows to mess with people following along from home.

The ultra-lovey “Your Body Is A Wonderland” helped launch a 24-year-old Mayer to stardom many moons ago. It has also remained the butt of many a “try-hard bro with acoustic guitar” joke throughout the ensuing decades. Mayer himself has often spoken about his “tumultuous” relationship with the “Wonderland” albatross around his neck in recent years, acknowledging its cringeworthy lyrics but choosing to give it grace as a memorable moment in his journey. He’s also attuned to the new Grateful Dead faction in his fanbase, as evidenced by the string of new Dead covers that have made their way into his solo shows since the end of Dead & Company’s Final Tour.

“Your Body Is A Wonderland” never did pop up in a Dead & Company show, but on Wednesday at Chicago, IL’s United Center, John Mayer leaned harder than ever into the inherent humor in his bizarre mix of musical credentials. First, he introduced a cover of the Grateful Dead’s “Bertha” to his solo acoustic repertoire and used it as a launchpad to move into his own “The Age of Worry” and back into the Garcia/Robert Hunter classic. Seemingly feeling emboldened by the well-received combo, Mayer then paired the bane of his catalog’s existence with perhaps the most sought-after number in the Dead’s live songbook, validating scores of memes with his first ever “Dark Star” > “Your Body Is A Wonderland” > “Dark Star” combo. Actually.

Related: John Mayer Announces New SiriusXM Channel, ‘Life With John Mayer’

As a giddy Mayer told the crowd ahead of the segment, “I’m gonna do this, I’m gonna do this. I’m not gonna set it up. This is gonna be the weirdest thing you ever saw in your life, and I’m proud to do it.” With that, he began to vamp on the opening chords to “Dark Star” as the bearded portion of the crowd cawed in approval. After a few measures, he stepped to the mic again. “I want you to mark it on the setlist, that this is technically ‘Dark Star’, and I’m going from ‘Dark Star’ into this next song,” he said as he strummed. “It’s a transition. I want you to mark the transition.”

The cheers intensified as “this next song” became “Your Body Is A Wonderland”. As fans vocalized along with the track’s final refrain, Mayer jumped back into his spacey “Dark Star” intro arrangement for another orbit. “You know what that just was?” Mayer asked the crowd when he was finished, a cheeky grin plastered across his face. “And I do this with extreme love for my brothers in Dead & Company. With all love and reverence, that was Dark Star > Your Body Is A Wonderland > Dark Star.”

Related: John Mayer Trio Debuts Grateful Dead Cover During Rare Gig At Crossroads Guitar Festival [Watch]

Watch a clip of John Mayer playing (and introducing, and narrating) his first-ever “Dark Star” > “Your Body Is A Wonderland” > “Dark Star” in Chicago below. Scroll down for a bonus clip of his solo “Bertha” debut and a full setlist from the show.

John Mayer will continue his solo tour through the end of October and into November. For a complete list of his upcoming dates, head here.

John Mayer – “Dark Star” (Grateful Dead) > “Your Body Is A Wonderland” > “Dark Star” – 10/18/23
[Video: RJ Curtis]

John Mayer – “Bertha” (Grateful Dead), “The Age of Worry” – 10/18/23
[Video: Katie Dzwierzynski]

Setlist: John Mayer | United Center | Chicago, IL | 10/28/23
Set: Heartbreak Warfare, Wild Blue, Emoji of a Wave, Queen of California, Why Georgia, Who Says, Waitin’ on the Day, Badge and Gun [1], In the Blood, In Your Atmosphere, You’re Gonna Live Forever In Me [3], Changing [3], Stop This Train, Bertha (Grateful Dead) [4] > “The Age of Worry” > Bertha (Grateful Dead), Dark Star (Grateful Dead) [5] > Your Body Is A Wonderland” > Dark Star (Grateful Dead) [5], Slow Dancing In A Burning Room, The Heart of Life, Walt Grace’s Submarine Test, January 1967, A Face to Call Home [6], Edge of Desire [6]

Encore: Comfortable, Free Fallin’ (Tom Petty)
[1] Dedicated to Bob Saget
[2] with “Wherever I Go” outro
[3] John Mayer on piano, vocals
[4] John Mayer solo debut
[5] Partial, instrumental, John Mayer solo debut
[6] John Mayer on double-neck acoustic guitar