John Mayer grew up in Connecticut listening to pop radio and picked up the guitar after discovering blues music, specifically the work of Steve Ray Vaughan. Within two years of first learning how to play, he was a notable performer at various local blues bars, and at 19, he enrolled at the Berklee College Of Music. However, Mayer soon realized he would rather perform music than study it, and would rather focus on serious songwriting than on virtuoso guitar playing. So in 1998, he returned to his adopted hometown of Atlanta and became a regular in the Atlanta club circuit, playing continuous gigs at nightspots like Eddie's Attic.

A year later, Mayer released Inside Wants Out, an album of acoustic-based tracks as well as several songs recorded with a full band. His stellar March 2000 performance at the South By Southwest Music Festival in Austin, Texas caught the attention of many record labels, who soon courted the young talent; Mayer eventually chose to sign with Aware/Columbia Records. He began recording his major-label debut, Room For Squares, that fall with producer John Alagia (Dave Matthews Band, Ben Folds Five), which featured a full electric band (including bassist David LaBruyere and Alana Davis/Genesis drummer Nir Zidkiyahu) and a more versatile singing style.

In summer 2001, Columbia re-released Room For Squares as a limited-edition, two-CD set with two previously unreleased Jimi Hendrix and Stevie Ray Vaughan covers and one bonus track recorded with Alagia entitled "3 X 5." The reissued CD also included seven remixed songs recorded with legendary producer Jack Joseph Puig (Eric Clapton, Weezer, Black Crowes) at Ocean Way Studios in Los Angeles. Mayer gained an incredibly strong fanbase during his first international tour to support the album, was hailed as the next Dave Matthews or Jakob Dylan, and received a Grammy nomination in 2002 for Best New Artist.

Although Mayer failed to win the award, which when to Norah Jones, it didn't dim his star. His label attempted to capitalize on his rising popularity with the release of the live album, Any Given Thursday. In September 2003, Mayer released his proper followup to Room For Squares, an album that promised in its title, Heavier Things.