Ten years ago, before his story had intersected with the legacy of the Grateful Dead by way of Dead & Company, John Mayer was at a creative crossroads. After notching a string of hit pop albums throughout the 2000s, Mayer began to deviate from the formula with 2012’s Born and Raised and 2013’s Paradise Valley, which can now be seen as crucial first steps toward his eventual journey down the Golden Road.

The guitarist, who emerged on the national scene at the dawn of the new millennium as a fresh-faced, Grammy-winning singer-songwriter, continued to gain popularity throughout the first decade of the 2000s leading up to 2009’s Battle Studies. While many Deadheads might be quick to lump it in with his earlier albums as “Mayer pop” due to its overtly romantic lyrical content, Battle Studies holds up as a great guitar record thanks to the brilliant and diverse mix of tones and effects adorning each track. If nothing else, it marks the first signs of Mayer’s sound shifting toward folk and Americana.

Related: John Mayer Picks Nine Of His Favorite Live Grateful Dead Cuts On SiriusXM [Listen]

Following the completion of the tour cycle for Battle Studies, Mayer entered the studio with veteran producer Don Was (Wolf Bros) and a new collection of musicians to begin working on the recordings that would appear on Born and Raised. Released in the spring of 2012, the 12-track album didn’t quite receive the same level of mainstream success and attention as his previous studio efforts. Almost a decade later, however, Born and Raised remains an excellent transitional snapshot of an artist on the verge of a dive down the Grateful Dead rabbit hole.

For the Born and Raised sessions, Mayer was accompanied by a lineup of players that included bassist Sean Hurley, seasoned session drummer Aaron Sterling (Taylor Swift, Kris Kristofferson), and Allman Brothers Band pianist Chuck Leavell. The sessions also included guest appearances from west coast folk-rock legends David Crosby and Graham Nash (CSNY) along with pedal steel guitarist Greg Leisz, who would later go on to perform regularly with Bob Weir’s Wolf Bros alongside Was. This lineup marked a notable change for Mayer, who had the benefit of being joined by John Mayer Trio drummer Steve Jordan and bassist Pino Palladino on his previous two albums.

Related: John Mayer Reflects On “Deeply Personal” Process Behind ‘Born And Raised’ On LP’s 10th Anniversary

With the guidance and experienced ears of Was and this veteran lineup, Mayer was able to capture a more relaxed aesthetic on Born and Raised while confidently applying Americana elements to his traditional pop-rock sound. The mushy, radio-friendly love songs heard on Battle Studies were replaced by songs containing deeper lyrical substance and personal self-reflection from Mayer.

John Mayer – Born and Raised – Full Album

From the opening acoustic riff to “Queen of California”, listeners are welcomed into a warm, organic-sounding sonic landscape, one where cowboys still sing campfire songs at the end of long days. It’s tough to ignore the parallels between the songs heard on the album and the cowboy tunes played by his eventual Dead & Company bandmate Bob Weir over the years.

Mayer opens up his lyrical vulnerability on Born and Raised tracks like “Age of Worry” and “Speak for Me”, which are also filled with great acoustic guitar licks throughout. Even the album’s lone love ballad, “Love Is A Verb”, delivers enough lyrical wisdom and instrumental minimalism to make it a quality musical advice piece.

The American folk music storytelling tradition also appears on Born and Raised in a way John Mayer hadn’t yet achieved to that point. On “Walt Grace’s Submarine Test, January 1967”, he delivers a feel-good narrative about a fictional character sung over quirky but fun instrumentation.

John Mayer – “Walt Grace’s Submarine Test, January 1967” (Official Lyric Video)

[Video: John Mayer]

There’s no doubt that the presence of Was, Leavell, Crosby, and Nash in the studio helped Mayer channel the spirit of 1960s and ’70s folk-rock. The experience also likely helping to further Mayer’s then-blossoming obsession with the Grateful Dead.

Around this time, Mayer told Billboard in 2011, the guitarist had been introduced to the music of the Dead when “Althea” came on Pandora at a pool party. “It was kind of a blind taste test — a station that wasn’t far genetically from the Dead played ‘Althea’ and I heard this riff and went, ‘What’s that?,'” Mayer explained. “I actually came in from being outside in the pool, I was dripping wet and had to see what was on the iPod. From there, I went [on] to know a few songs and started recognizing pieces of songs.”

The window for jamming opportunities was another theme implemented by Mayer for the first time at points throughout Born and Raised. These potential jam sections built into the songs are enjoyably noticeable during the extended outro of “Queen of California” and during the ultra-dreamy middle section of “If I Ever Get Around To Living”.

Unfortunately for Mayer, a throat granuloma emerged prior to the completion of the album, and sidelined him from performing—or even talking—for an extended period of time. It would be 18 months until he was able to return to singing in 2013, even though Born and Raised was released by Columbia the previous May. Without the ability to tour or do interviews to promote the album, the material included on Born and Raised literally spoke for him, and formally introduced his fanbase to “John Mayer 2.0”.

John Mayer, Don Was – Born and Raised Tour Interview

[Video: John Mayer]

After being sidelined and left without the option to speak while recovering from the throat granuloma between 2011 and 2012, Mayer moved to Montana. His new home in Big Sky Country only deepened his connection with the cowboy aesthetic, as the western themes heard on songs like “Born and Raised – Reprise” would carry over into the track listing of its studio successor, 2013’s Paradise Valley.

Teaming up in the studio again with Sean Hurley, Aaron Sterling, and Chuck Leavell, Mayer once again nailed the modern soft-rock sound on Paradise Valley, even if he did dial back just a bit on the Americana in exchange for his return to love songs with “Paper Doll” and “Dear Marie”.

“Waitin’ On The Day” does a fine job of showcasing Mayer’s knack for achieving strong guitar tones and his ability to find the right places to utilize them over a good melody. He also manages to leave fans with a few tracks worthy of an American road trip playlist in “You’re No One Until Someone Let’s You Down”, “On The Way Home”, and his cover of J.J. Cale’s “Call Me The Breeze”. In contrast to Born and Raised, however, Paradise Valley tilts slightly back to the pop spectrum, thanks mainly to guest contributions from Katy Perry and Frank Ocean.

John Mayer – “Waitin’ on the Day” (Studio Acoustic)

[Video: John Mayer]

John Mayer  – Paradise Valley – Full Album

Mayer underwent a hiatus of sorts from his solo output following Paradise Valley—though not for lack of gigs. By February of 2015, he was jamming with Bob Weir on The Late Late Show. By that Halloween, he was the lead guitarist for Dead & Company, touring the country with the surviving members of the Grateful Dead and helping to keep the spirit of the music alive.

While he has moved back toward the pop realm on ensuing solo releases like 2017’s The Search For Everything, the role in Dead & Company and the presence of the Grateful Dead have split off into an equally popular parallel narrative for John Mayer.

Almost ten years later, Born and Raised and Paradise Valley both hold up as enjoyable and stylistically telling predecessors to his transition into the world of the Dead.

For a full list of Dead & Company tour dates this summer, head here.