Year: 2000

John Mayer is one of the biggest success stories to come out of SXSW because of how organic his discovery was. In 2000, the festival was still limited to unknowns looking to get noticed by labels. After performing at SXSW, the guitarist was picked up by Aware Records, the label that led him to sign with Columbia and helped him drop his first album—albeit online only—Room For Squares, which was subsequently re-released by Columbia. Mayer's debut album had breakout hits like "Your Body Is A Wonderland," "No Such Thing," and "Why Georgia." Three years after Mayer's SXSW debut, he won his first Grammy for Best Male Pop Vocal Performance.