John Mayer’s debut album masterfully navigates the tricky tightrope between pop accessibility and artistic credibility. Raised on guitar greats such as Stevie Ray Vaughan and Albert King—Mayer posthumously inducted the latter into the Rock and Roll Hall of Fame in 2013—Room for Squares announced the arrival of an equally adept player, as comfortable in the realms of acoustic folk-pop (“Why Georgia”) as he was noodling on a snaking funk riff on “Neon” and embarking on a Santana-esque middle-eight in “83.” That Mayer used those skills to mold warm, FM-friendly pop songs made him something of an anomaly in the early 2000s, a time when the pop charts were dominated by the second wave of nu metal (Staind, System Of A Down, Disturbed) and pop/R&B megastars like Janet Jackson, Destiny’s Child, and Alicia Keys. (The closest charting artist to Mayer was Dave Matthews—coincidentally, Room for Squares producer John Alagía also helmed multiple Dave Matthews Band albums.) Having dropped out of Berklee College of Music to move to Atlanta, it was there that Mayer crafted many of the songs on his major label debut, signing with Columbia after independently releasing 1999’s Inside Wants Out. Cribbing its name from Hank Mobley’s 1963 album No Room for Squares, that Mayer tweaked the title slightly is a fitting representation of the record—one that foregoes any airs of cool for lyrically earnest guitar-pop that, on occasion, borders on the nostalgic and naïve. Energetic opener “No Such Thing” finds Mayer longing to return to the halls of his high school and scream the knowledge he’s gained about the real world beyond the cliques and pressures of the classroom; “My Stupid Mouth” recalls the promise he’d make to himself at the beginning of each school year to be quiet and tactful, only to break that promise by the end of the first lesson, a habit that’s now cost him a relationship (“I’m never speaking up again,” he laments); “Why Georgia” is inspired by his lean days before finding success, when he’d have to fight the urge to give up and return home. Matters of the heart also play a prominent role, whether it be the fantasy of “Love Song for No One,” written about a partner he hadn’t yet met, or the lust-filled romance of “Your Body Is a Wonderland,” Mayer’s whispered, breathy baritone setting pulses racing as he teases, “You want love? We’ll make it/Swim in a deep sea of blankets.” Mayer would go on to flex his guitar chops more extravagantly on outings such as the John Mayer Trio’s 2005 live album Try!, not to mention his stint with the Grateful Dead offshoot Dead & Company. Here, though, it’s Mayer’s songwriting that remains the focus, the foundation on which he launched—and has maintained—his career.