After a short stint at the Berklee College of Music, John Mayer set down roots in Atlanta, where his music career really got started. After a year in Atlanta, he released his debut solo album, Inside Wants Out, in 1999. At the same time, he became a regular in the Atlanta club circuit, playing a steady stream of shows at venues like Eddie's Attic. An appearance in March 2000 at the South by Southwest Music Festival led to a recording contract with Aware Records, a subsidiary of Columbia. He began recording his major label debut, Room for Squares, that fall with producer John Alagia, who had previously worked with artists like Dave Matthews and the Ben Folds Five. Mayer's first album had been a decidedly acoustic effort; in contrast, Room for Squares featured a full electric band and showed the work of its producer with its funky hooks and an emphasis placed on Mayer's versatile, smooth voice, which bore more than just a stylistic resemblance to Dave Matthews. Aware's parent company Columbia re-released Room for Squares in the summer of 2001 adding one bonus track, and also offered a very limited edition two CD set including a disc with two previously unreleased covers.

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