One of the most successful pop singers of the 2000s, John Mayer was pigeonholed early as a soft, sensitive songwriter, and has since put much of his energy into defying that label. In four years, he won five Grammy Awards, including three for best male pop vocal performance. Three of his major-label studio albums have gone platinum or multi-platinum. He established him as a romantic heartthrob, but when the most sentimental song on his second album, “Daughters,” was released as a single despite his objections and became a huge hit, Mayer decided to alter his career by emphasizing his work as a blues guitarist. He collaborated with several blues legends and began recording with a tight trio. Though such a move generated some predictable criticism, given his musical reputation and middle-class upbringing, his recordings with the trio have earned him a measure of critical respect as well as continued commercial success.

Mayer grew up in Fairfield, Connecticut, where he became a fan of classic blues guitarists. “I was 15 years old, with my room plastered with posters of Stevie Ray Vaughan and as many Albert King photos as I could have, which wasn’t many,” he told Entertainment Weekly. He briefly attended Berklee College of Music in Boston, where an overdose of intense guitar performances drove him to explore soft, melodic ballads. In 1998, after he dropped out, he moved to Atlanta, where he became a frequent performer at music clubs. “Atlanta’s my musical home,” he says in 2003. “It really was the place where I really came alive.”

While in Atlanta, Mayer released his first album, Inside Wants Out. He appeared at the prestigious South by Southwest Music Festival in March of 2000, and his performance there won him a contract with the Columbia Records’ Aware Records. He went into the studio in late 2000 to record his major-label debut.

The new album, Room For Squares, included re-recordings of some songs from Inside Wants Out with more punch and instrumentation. The album, released in September of 2001. The first song, “No Such Thing”, with an alienated teenager defying the expectations of “prom kings” and “drama queens” and imagining a sort of emotional revenge at his ten-year high school reunion, appealed to a wide audience of young, lonely misfits.

Mayer’s popularity grew steadily throughout 2002. Room For Squares was certified platinum by that summer, on the way to going double platinum. Mayer spent much of 2002 touring nationwide to promote the album, selling out concert halls with as many as 10,000 seats. Columbia/Alive re-released Inside Wants Out to satiate fans’ appetite for new Mayer songs. The following February, he won a Grammy for Best Male Pop Vocal Performance.

Room For Squares, Mayer told Entertainment Weekly, was his attempt “to make the most mature-sounding immature record in the world,” that is, an album with lyrics from a youthful perspective but music inspired by sophisticated influences. “A lot of young artists right now are drawing from an incredibly shallow pool of inspiration,” he complained.

Another aspect of Mayer’s success was, undeniably, his good looks—his “deep, searching brown eyes” and “l(fā)uscious, curly brown hair,” as USA Weekend described. Combined with his romantic lyrics, his looks and 6-foot-3 frame quickly led him to heartthrob status. That seemed to surprise Mayer. “If you can see inside my brain and what I’m trying to do onstage, the last thing that comes to mind is [to] make people swoon,” he said.

Though Mayer titled his follow-up album Heavier Thing , critics dubbed it another soft, pleasant, but not edgy affair. Mayer said the album showed him at his most emotionally honest. The record company chose the song “Daughters” as the single from the album, over Mayer’s strong opposition. It was the softest, most sentimental song on the album, and Mayer feared it would forever pigeonhole him as a sensitive guy. “I saw that as career death,” he later told Rolling Stone . Meanwhile, the record company proved to be right that the song would be a strong single: “Daughters” won Mayer his second Grammy, for Song of the Year.

After that, Mayer began to resist the sensitive singer-songwriter tag. “I got pigeonholed,” he told Entertainment Weekly. “Everybody [was going], ‘You’re doing good,’ but I felt terrible. They had the wrong man. So I had to jam the door open.” To change his career path, Mayer formed the John Mayer Trio, a band that included bassist Pino Palladino, and drummer Steve Jordan, who had recorded sessions with Clapton and Bob Dylan. They embarked on a tour of small theaters that sold out around the country. The move pushed Mayer to test the limits of his musicianship.

Meanwhile, Mayer also began working as a guest musician with several legendary and popular musicians. His insistence in interviews that he was a bluesman upset some critics. But when the trio released a live album, Try! John Mayer Trio Live in Concert in 2005, People reviewer Chuck Arnold, called the live album “exciting,” praising Mayer’s “surprising new blues, funk, and jazz colors.”

Mayer spent a few years recording his next studio album, Continuum. The collection of mostly soul-influenced songs included some radio-friendly pop ballads, but also showed off his blues-guitar skills. He declared the new album his best. “Continuum is kind of like my thesis paper,” he Entertainment Weekly. “It’s the one I feel best about. I’ve finally got it right.”

Mayer has also explored comedy and magazine writing. By 2007, Mayer’s efforts at being taken more seriously were succeeding. In February, he won two more Grammys. “Waiting on the World to Change” won him his third award in four years for best male pop vocal performance, and Continuum won best pop vocal album. Then, in May, Time named him to the Time 100, its list of the world’s most influential people. He spent the rest of the summer of 2007 touring to support Continuum and writing songs for a new album.

Nominated for five awards in 2009, Mayer picked up two trophies at the 51st Grammy Awards: Best Male Pop Vocal Performance and Best Solo Rock Vocal Performance. “It’s always been an honor for being a musician,” Mayer said of his win during his acceptance speech. Mayer’s latest studio album, Battle Studies, topped the Billboard albums chart. Rolling Stone praised Mayer in an album review, calling his latest release “a real study in craftsmanship and understated guitar ninja-dom.”

After spending two years out of the spotlight, Mayer returns in 2012 with his latest album, Born and Raised, which tops the Billboard 200 chart making it his third No. 1 album. “I hope people want to receive this music. I have so much that I need to say – I hope I get a chance to say it. I hope people are interested,” he tells NPR of his return to music.