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After playing the guitar for several years, Mayer enrolled in the Berklee College of Music in Boston, Massachusetts, at the age of nineteen. After a semester or two, he chose to cut his studies short in favor of a move to Atlanta, Georgia. With his fellow friend and bandmate, Clay Cook, he began his career in earnest there, quickly making a name for his band LoFi masters in the local coffeehouse and club circuit, in venues like Eddie's Attic. After the band LoFi masters split, Mayer began his solo career. With the help of local producer/engineer Glenn Matullo, John Mayer recorded Inside Wants Out. Clay Cook is also cited as the writer of many of the songs from the album Inside Wants Out, most notably, the ballad Comfortable. This EP ultimately contributed to John Mayer being signed as a major upcoming artist.

Mainstream success

In 2001, two years after releasing the independent EP Inside Wants Out, Mayer released his first major label album, Room for Squares. This "debut" included several of the songs that previously had been released. By 2002, Room for Squares had spawned several radio hits, including "No Such Thing," "Your Body Is A Wonderland," and, ultimately, "Why Georgia." In 2003, he won the Grammy Award for Best Male Pop Vocal Performance for the 2002 release of "Your Body Is a Wonderland." In his acceptance speech he said "This is soon. I'll try to live up to it."

In 2003, Mayer released the follow-up album, Heavier Things. This album also brought critical and commercial success. Although the album did top the charts for a time, it ultimately did not sell as well as Room for Squares. The first single from this album, "Bigger Than My Body," was thought by some to be Mayer's attempt to demonstrate that he was not just a one-trick pony, i.e., that "Your Body Is A Wonderland" did not define him. Mayer's most successful single to date, "Daughters," yielded Mayer a Grammy for Song of the Year in 2005. For this award, he beat contenders Alicia Keys and Kanye West. He dedicated this award to his grandmother, Annie Hoffman, who died in May 2004. He also won Best Male Pop Vocal Performance, beating Elvis Costello, Prince, and Seal for the Award.

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