Art Alexakis suffered through a troubled youth, beginning with his father walking out when Alexakis was a child. Financial hardships pushed his family into the slums of Los Angeles, where Alexakis became a heavy drug user. During his teenage years, Alexakis was shuttled around the country between various family members (including a brief period in Houston living with his father's new family), but the drug addiction persisted. Eventually, Alexakis suffered a near-fatal cocaine overdose, which finally pushed him to clean up. In the late 1980s, Alexakis played in a short-lived rock band in Los Angeles called Shakin' Brave, where he began to hone his songwriting skills. Frustrated by the inattention of the L.A. music scene, Art relocated to San Francisco, where he fell into the then-burgeoning cowpunk scene.