John Mayer has always been something of a critical bête noir. His gentle, mawkish songwriting juxtaposed against his caddish, clownish behavior has created a friction that is at best unappealing and at worst artistically dishonest. At the height of his fame in the mid- to late-’00s, as the guitar virtuoso and singer-songwriter was vacuuming up Grammys for harmless pablum like “Daughters” and “Say,” he became known for a notorious string of celebrity exes, from Jennifer Aniston to Jessica Simpson to Taylor Swift. Once a dependable source of amusing copy, he beat a forced retreat from the Hollywood media sphere after his increasingly incendiary interviews culminated in the use of a racial slur, followed by his tearful onstage apology during a February 2010 show in Nashville.

Yet since Mayer has stepped out of the spotlight, he has entered an unlikely career renaissance. His three solo albums since his self-induced purgatory have been understated, exploratory; his mind expanding according to the size of his hat. His work when he is not billed under his own name, especially, has been fascinating to behold. Mayer blazes an uncredited guitar solo on one of the best songs on one of the 2010s’ greatest albums, Frank Ocean’s Channel Orange, and since 2015, he has been touring, with Dead & Co., as the de facto leader for what remains of the Grateful Dead. To replace Jerry Garcia and be warmly accepted into the Deadhead community is not something you could have predicted from the guy who once donned a Borat-inspired lime-green “mankini” on a festival cruise ship called the Mayer Carrier.

But at the start of the millennium, Mayer was just a nobody with a website, exploiting his wide-eyed lyrical clarity and chopsy musicianship to capture a teen audience readied by the college-quad strums of Dave Matthews Band and David Gray. “Welcome to the real world,” he sings at the start of Room for Squares. The giveaway is that he’s attributing these words not to himself, but to an unspecified authority figure. His major-label debut, released when he was 23 but largely written when he was at least a couple of years younger, is not the real world. Its opening track, “No Such Thing,” denies that one even exists, “just a lie you have to rise above.”

Room for Squares offers a willfully innocent fantasy. Life can be as safe, as self-consciously cute, as broadly appealing as a really popular sitcom. The Crayola-bright soundtrack echoes the music of the protagonist’s childhood, particularly early MTV hits by the Police and Elvis Costello. He wins over audiences with sincerity and admitting his faults; the music is smooth because people are not. What Mayer describes on the album as a “quarter-life crisis” is also a privileged space, a temporary sanctuary from becoming an adult. This is a place where it’s OK to make yourself vulnerable as you figure out who you’re going to become.

As a kid in suburban Connecticut, Mayer wanted to play the guitar after watching Michael J. Fox in Back to the Future. A neighbor passed him a tape by Stevie Ray Vaughan in 1990, the year Mayer turned 13, and he grew worryingly obsessed. “Everyone else had Nirvana, and I was skipping class, reading the Buddy Guy biography Damn Right, I’ve Got the Blues, cutting out the pictures when I was done,” he has said. A few years later, when he was 17, Mayer told his mother and father—an English teacher and a high school principal, respectively—he wanted to skip college and become a musician. They did not react well. Mayer began to suffer from panic attacks. He dreaded landing in a mental hospital.

After graduating from high school in 1995, Mayer worked for two years at a gas station and played in blues clubs at night. When he realized that his “dreams of staying in Connecticut and becoming a star from home,” as he once put it, weren’t going to happen, he briefly enrolled in Boston’s Berklee School of Music. It wasn’t a fit, and, wanting to be “listenable,” he moved to Atlanta, where he and co-songwriter Clay Cook, later of the Zac Brown Band, won an open-mic contest as a short-lived duo, Lo-Fi Masters. Mayer self-released a coffeehouse-tinged solo EP, Inside Wants Out, in 1999. By the fall of 2000, anyone could hear early versions of several Room for Squares songs via his page on MP3.com, which acted like MySpace, SoundCloud, or Bandcamp for unknown artists right before the dotcom bust. In a nod toward the jam band scene, Mayer also encouraged fans to tape his live shows and circulate the recordings.

If Mayer initially gravitated toward the blues, he escaped whatever was on his trail through his accessibility and relentless eagerness to please. (You can picture the genre’s fabled hellhound walking away thinking, “What a nice young man.”) Room for Squares shares a producer, in John Alagia, with Dave Matthews Band, who came up a lot as a comparison for Mayer’s percussive acoustic guitar playing and slightly congested vocals. But the album feels more polished than that. “I was trying to make the most mature-sounding immature record in the world,” Mayer once said, adding later, “It’s almost a concept album about being really shamelessly melodic.” His ambitions leaned toward pop. The title, which happens to be flipped from jazz great Hank Mobley’s 1963 album No Room for Squares, is Mayer laying out a welcome mat. It’s as if to say: No prerequisites to your enjoyment here.

The most all-around shameless track on Room for Squares is its mid-tempo slow jam, “Your Body Is a Wonderland.” Squint hard enough, and you can almost see the sun peeking between dorm-room window curtains. Like everything on the album, it’s a bit much—“Your skin like porcelain” is an objectively bad lyric, and “bubblegum tongue” is just ridiculous. But if you grew up listening to ’90s R&B, it isn’t that much more ridiculous than Hi-Five smooching and telling on “I Like the Way (The Kissing Game),” or Shai asking to be your “Comforter.” Mayer himself quipped, during a video-streamed 2000 gig, that “Wonderland” should start with a husky spoken-word intro: “...And in the morning, girl, I’m gonna pour you a bowl of Count Chocula, and I’m gonna pull some of the oat pieces out so it tastes like there’s just more marshmallow.” As bubblegum-tongue afternoon delights go, it’s an endearingly silly ode, both tender and curious. If Lady Bird could rescue “Crash Into Me,” maybe there’s hope for “Wonderland” yet.

Mayer is at his most affecting here when he’s singing about feeling lost and scared. The soaring chorus of “Why Georgia” nails a particular youthful anxiety that’s quite different from what critics usually mean by “angst,” and maybe a bit more sheltered, too: “I wonder sometimes about the outcome of a still-verdictless life/Am I living it right?” On “Not Myself,” more like an early Coldplay song with its lyrical economy and sweeping, open chords, Mayer trusts a friend to wait him out if “I lose my worried mind”: “Suppose I said, you’re my saving grace,” he booms, as much as Mayer ever booms. When you’re in a crowd of people mouthing these words back alongside you, you might feel a little less lost and scared yourself.

He would soon be routinely touted as a “heartthrob,” but these are the songs of a young person who has spent a lot of solitary hours in their bedroom. On “83,” which makes plain the early MTV influence by shouting out the Police’s “Wrapped Around Your Finger,” Mayer longs “to be 6 again,” and the Peter Pan syndrome is intensely vivid: “That’s my plastic in the dirt,” he sings, a Lost Boy wryly alerting future homeowners to lost toys. “Great Indoors” uses blocks of electric guitar and more Mayer wordplay to empathize with a TV-gazing shut-in. “Love Song for No One” is one of those ditties you can’t believe hadn’t been written yet. Here, again, the perspective is curiously childlike: “I could’ve met you in a sandbox,” he claims. “Back to You” has a gentle groove distantly reminiscent of Jeff Buckley’s “Everybody Here Wants You”—it struts, as much as Mayer here ever struts—but his lover is just a silhouette, who wouldn’t even smile in their final photo.

When Mayer steps out of the bedroom, he’s still awkward. On the bouncy “My Stupid Mouth,” with its goofy false ending, he’s as winsome about ruining a date as he is about engaging in foreplay on “Wonderland.” On “Neon,” the object of the narrator’s affection is out soaking up Atlanta’s nightlife, and why shouldn’t she be? Mayer was a non-punk straight-edge guy; the song is mainly a fine showcase for his irksomely giant-thumbed guitar flash. Mayer gets in more licks on “City Love,” a blues-drizzled love letter to New York romance where he unforgettably humblebrags, “She keeps her toothbrush at my place/As if I had the extra space.” Listening back, you can sort of sense his ego about to balloon.

Critics have long been averse to this record’s charms because, at its best, Room for Squares is an antidote to exclusion. It’s a coming-of-age album that refuses to pose as rebellious, a guilty pleasure that challenges the idea there should be guilt in pleasure. Arriving when assembly-line teen-pop and aggro nu-metal still ruled the airwaves, the album proved that pop could be delivered by the precocious boy with the guitar next door. The confident vulnerability of early Drake and the sharp-eyed clarity of early Taylor Swift, but also the man-child strums of Ed Sheeran, Shawn Mendes, and the Jonas Brothers, all have precursors here. Teenagers screamed. Elton John raved.

Room for Squares is also a time capsule. Columbia issued the album a week after the attacks of September 11. Nostalgic reassurance was in high demand, and it’s possible that only children of sanitized ’80s America would recognize the music’s cozy solace. Mayer’s big-tent pop now feels like the last gasp of the old monoculture in the face of digital fragmentation, but it also reminds me of all those movies where the straight, white, middle-class, and (cis) male is presented as the default perspective; the fans were a diverse bunch (including the Roots’ Questlove), but the women in his songs are faceless. And while sincerity was Mayer’s stock-in-trade—he wields it “like a pitchfork,” Time’s Josh Tyrangiel later wrote—he has turned out to be more of a scoundrel, or perhaps an enigma, than some doe-eyed romantic. John Mayer is constantly performing “John Mayer,” whether he wants to or not.

I’m not sure the music we loved when we were younger becomes less valuable just because we no longer need what it has to offer. Over the years, I’ve adored plenty of albums that reflect the richly varied ways we are each different, individual, weird. I listened to Room for Squares the most when I wanted to feel normal. Not “normcore”: Just normal. A little less alone; a little more accepted. “You will know what all this time was for,” Mayer promises as “No Such Thing” rings to a conclusion. I just know that expressing what’s true, for yourself or for a group of people, can make a bigger difference than anyone realizes in the moment. Room for Squares, for all of its baggage, remains a little guitar-pop utopia where it’s OK to keep discovering ourselves as we go along.