After including him in Aware Festival concerts and his songs on Aware compilations, in early 2001, Aware released Mayer's internet-only album titled, Room for Squares.
During this time, Aware concluded a deal with Columbia Records that gave Columbia first pick in signing Aware artists.
In February 2003, Mayer released a live CD and DVD of a concert in Birmingham, Alabama titled Any Given Thursday, which included songs previously not recorded, such as "Man on the Side", "Something's Missing", and Covered in Rain".
Reflecting on the incident, Mayer said, "That was the moment the songwriter in me was born", and he penned his first lyrics the night he left the hospital.
With the help of local producer and engineer Glenn Matullo, Mayer recorded the independent EP Inside Wants Out.
Mayer's secondary career pursuits extend to television hosting, comedy, and writing; he has authored columns for magazines such as Esquire.
He supports various causes and has performed at charity benefits.
He is a watch aficionado (with a collection he values in the "tens of millions" of dollars), and has been on the jury at the Grand Prix d’Horlogerie de Genève. According to Mayer, his fascination with Vaughan started a "genealogical hunt" that led him to other blues guitarists, including Buddy Guy, B. King, Freddie King, Albert King, Otis Rush and Lightnin' Hopkins.
When Mayer was seventeen, he was stricken with cardiac dysrhythmia and was hospitalized for a weekend.Even so, the album enjoyed a generally favorable reception, though was less commercially successful than his previous work.After extensive treatments for his vocal problems—and a two-year hiatus—Mayer began performing as a singer again in January 2013, and that year released the album, Paradise Valley.After his appearance at the 2001 South by Southwest Festival, he was signed to Aware Records, and then Columbia Records, which released his first EP, Inside Wants Out.His following two full-length albums—Room for Squares (2001) and Heavier Things (2003)—did well commercially, achieving multi-platinum status.Because of this, he removed the top half of the Grammy and gave it to Keys, and kept the bottom part for himself.