For an indiscernible amount of time in the ’00s, I remember hearing John Mayer’s “No Such Thing” everywhere. Echoing from new SUVs parked at the intramural soccer matches, playing in T.J. Maxx and Target, the muzak for the shopping mall food court. It was that kind of super-safe pop-radio token, the kind that you’d hear while running around doing errands with your parents. Years later, I remember watching The Office’s Christmas special, in which there’s a scene where Steve Carell and Ed Helms serenade some Benihana waitresses they brought back to the office party with Mayer’s noxiously syrupy “Your Body Is A Wonderland.” But the context was different by then. It was the end of 2006, and that was an older song of Mayer’s, as ripe for parody as any song in history. But Mayer had changed. Theoretically. That was the same year he released his third solo album, Continuum, the one that functioned as a definitive bid for legitimacy within the rock establishment. Earlier this summer, I could hear distant strains of him playing with what remains of the Grateful Dead, on the final night of Bonnaroo. It has been a strange road to this place.

Despite the fact that Mayer’s music has predominantly existed in a successful and highly inoffensive lane sonically, he has one of the more bizarre trajectories in recent pop recollection. In the beginning of the ’00s, he released Room For Squares and Heavier Things, two fizzy, glossy pop records firmly in the tone of the times. A few years later came the pairing of the John Mayer Trio’s live album Try! and Continuum, the very clear re-branding move. But by 2009 he was back to Adult Contemporary pop on Battle Studies. Then, in this decade, he was back in the respectable waters of old country, California singer-songwriters, and folk affectations on the pairing of Born And Raised and Paradise Valley, released in 2012 and 2013, respectively. He’s got another record on the way now, which was put on hold while he toured with Dead & Company.

There are certain through lines. Mayer’s voice is, predominantly, like Rice Krispie treats. Artificially and blandly sweet, broadly appealing due to its middle-of-the-road character, temporarily and emptily satisfying. In the earlier days, he sounded like a smoothened version of Dave Matthews, who had plenty of his own mainstream success around the time of Mayer’s rise, but who also sounds like a Muppet on bath salts half the time. In those earlier days, it was easy to see Mayer as one of those too-sugary, too-earnest peddlers of platitudes built for mass consumption. If you altered a handful of elements in songs like “No Such Thing” or “Bigger Than My Body,” it isn’t hard to imagine them as solid power-pop songs, or big atmospheric Brit-rock tracks, or something. But mired as they are in that weird early-’00s Adult Contemporary rock sheen, I had Mayer slotted in alongside acts like Jason Mraz, James Blunt, the Fray, or Daniel Pewter, the guy responsible for that god-awful hit “Bad Day.” (Even though, chronologically speaking, some of those songs were contemporary with when Mayer was re-branding, but that breed of ’00s pop hit is hard to divorce from the initial iteration of Mayer.) From the beginning, he was building a foundation that would forever stop him from being entirely “cool.”

That was the music. But over the course of that decade, Mayer proved himself to be an, uh…interesting character. He shed the innocence of his earlier image and, through a string of high-profile relationships and the way he discussed them, started to come off as an obnoxious bro who played sensitive songs “for the chicks, man,” or even as a womanizer. This is the guy who — during a 2010 interview where he was asked about dating black women — infamously told Playboy, “My dick is sort of like a white supremacist. I’ve got a Benetton heart and a fuckin’ David Duke cock. I’m going to start dating separately from my dick.” His music was aggressively pleasant and palatable, but he was proving himself to be a wilder, and occasionally caustic, figure in real life.

PR flare-ups like that eventually led Mayer to remove himself from the spotlight, and to return after having done some spiritual accounting. But outside of the offensive interviews, he had already shown a self-awareness that allowed him to mess with the machinery of popstardom. He was always willing to poke fun at himself. Always conscious of how he was perceived. Which brings us to the self-consciousness of Try! and Continuum, the collective pivot point without which Mayer might’ve stayed a relic of ’00s pop.

It isn’t possible to talk about Continuum without talking about Try!, which preceded it in 2005. In case you were going to miss the point, Mayer opened that record with a song called “Who Did You Think I Was.” What followed was a jammy, blues-rock (would-be?) power-trio record, with Mayer accompanied solely by Steve Jordan on drums and Pino Palladino on bass. It was a nearly complete departure from the music Mayer had released thus far. He indulged his Hendrix worship, favoring a bunch of busy guitar parts that came off like Mayer, formerly pent-up, bursting to erase the narrative and reputation of the preceding several years. (In case you were going to miss the point, he also covered Hendrix’s “Wait Until Tomorrow” on that record, which was actually not the first nor the last Hendrix cover he’s performed.) He covered Ray Charles’ “I Got A Woman,” a de rigueur retro option at the time following the 2004 biopic Ray and Kanye’s “Gold Digger” earlier in ’05. It played as a refutation of where he’d been before, the announcement that he could fit into a more vaunted lineage of gifted guitar players and bluesmen.

In a way, this was what some were always waiting for Mayer to do. Room For Squares accrued the reputation it did, and had the kinds of songs it did, but it was clear from the beginning that Mayer was a preternaturally adept guitarist. Before the Trio record and Continuum, he’d already garnered the respect of elder statesmen. And after that early success, he began playing with (and occasionally recording with) artists like Eric Clapton and B.B. King. (Eric Clapton isn’t the most prestigious classic rock co-sign, necessarily, considering like…of course Eric Clapton likes an Adult Contemporary blues-fanatic. But even so, Slowhand’s blessing plays as a good report card within the classicist realm that prizes virtuosic playing.) So, then, Mayer’s mid-’00s classic rock turn was like a belated awakening of the artist that might’ve always been lying latent underneath the pop songcraft. He grew his hair out and started talking about smoking weed. In case you missed the point.

Try! felt like a workout: a release that totally showcased Mayer’s guitar-playing front-and-center for the first time, a warmup for the next studio album that could serve as the reestablishment as his career. That’s where Continuum came in.

The thing is, Continuum wasn’t exactly Mayer’s big rock record. Compared to the unhinged, rollicking nature of Try!, Continuum reined it back into tight, pop forms, and found Mayer dabbling in blue-eyed soul moreso than sprawling blues-rock. It had “Waiting On The World To Change,” a nod to Marvin Gaye rather than Hendrix or Stevie Ray Vaughan, and simmering mid-tempo fare like “Vultures” and “Slow Dancing In A Burning Room,” a song laced with Clapton-esque guitar lines. It had “Belief,” a song that wasn’t altogether dissimilar from his earlier work, but was just more lived-in, better, more mature. It had a cover of Hendrix’s “Bold As Love,” which many seemed to give him props for having the guts to do, but it always struck me as not only on-the-nose but mostly pointless — you can’t have that song without its celestial outro, which Mayer doesn’t try to reproduce here (and which nobody should try to reproduce anyway). All this was cleaned up and tidied compared to what Try! had suggested might be around the corner. And that worked. It allowed Mayer to explore these influences while not giving up on the pop landscape entirely. Maybe it scanned as covering his ass. Maybe it was a way of doing this without going full retro-revivalist.

Ultimately, what matters is that Continuum was good. It was a better record than the ones he’d released before. Mayer’s vocal delivery means that, no matter what, this still sounds like a contemporary soft-rock version of the revered stuff he was trying to quote. But that’s all right, if it’s something you can get past. “Vultures” was calmly infectious, as was the sultry comedown of “I Don’t Trust Myself (With Loving You).” Though “Waiting On The World To Change” sometimes gets sidelined as a the pop concession if you’re talking to the rock purists who’d welcomed Mayer into their tribe, it’s a great pop song that succeeds in cribbing an old mold for something new, even if the idea of Mayer gesturing at politics and The State Of Things is a bit much. And “In Repair” builds to a stunning conclusion, all beautiful intersecting guitar licks while Mayer gently mulls over the refrain of “I’m in repair/ I’m not together/ But I’m getting there.”

It still isn’t a particularly cool record, and he’s shot himself in the foot plenty of times in the ensuing years. So it wasn’t a clean line, his move from baby-faced popstar with evident talent perhaps misspent, to full-fledged “serious musician.” He went back to some of his old musical tricks later on, he said dumb things. Regardless of all that, he also succeeded at exactly what he intended. After Continuum, there was a different tone to how Mayer was discussed as a person, a guitarist, and a songwriter. He had prominence already, but now it was secured. And now he had respect. Now he could put out a country record, if he damn well felt like it. Now he could tour with the Dead, but he could also date Katy Perry.

In hindsight, it makes you wonder: Was the beginning of Mayer’s career, with all its overwhelming earnestness, actually a cynical ploy? A way of gaming the system, to get himself in and established, so he could make the music he was really passionate about? Or was it legitimate: the guy who came up on blues-rock guitarists, made pop for his time, before rediscovering what really made him tick? Either way, it’s now hard to figure out where John Mayer lives, exactly. You will still hear “No Such Thing” and “Your Body Is A Wonderland” in mall food courts. You probably will forever. But you also have the inherently strange and idiosyncratic nature of Mayer as a pop figure, the fact that he’s a popstar blues-indebted guitarist in an era where that is, well, uncommon. He got the fame and wealth and success, and eventually coupled that with respect within the circles that came out of the same stuff he loved — the people who like Derek Trucks, who like guitarists, who like the Dead, who go to Bonnaroo. It still comes across as some kind of paradox that Mayer — performer of the eyeroll-inducing “Daughters,” with a sometimes-offensive celebrity persona through a good chunk of his career — made it into that world, and that he seems more comfortable there. Who knows what comes next for this guy. If the patterns hold, it’ll either be something boring and safe, or something totally unpredictable and potentially exciting.