At a young age, Alexakis' father walked out on the family, leaving Alexakis, his mother, his brother, and his three sisters to fend for themselves. Not long after, financial difficulties forced Alexakis' mother to relocate the family to the Mar Vista Gardens housing projects in California, located in Los Angeles near Culver City (Mar Vista Gardens is near, but not in, the Mar Vista neighborhood).

There, Alexakis came in direct contact with the area's criminal and drug culture. Alexakis' brother George died of a heroin overdose when Alexakis was twelve. A lyric in the song "Heroin Girl" refers to his mother overhearing a police officer describing his brother's death as "just another overdose." About a year later, Alexakis' girlfriend OD'd. Not long after her death, Alexakis attempted suicide by getting stoned, filling his pockets with sand, and jumping off the Santa Monica Pier. He claims the voice of his brother George compelled him to survive.

Regardless, Alexakis' drug addiction continued. Over the next eight years, he was shuffled around between various family members all over the country. He spent a brief period in Houston, Texas, living with his father, and a period in Roseburg, Oregon, living with his sister, a born-again Christian, and her husband. Eventually, he returned to LA to live with his mother. He attended journalism school for a time, and worked as a music reviewer for The Evening Outlook, a small newspaper in Santa Monica. Eventually, a near-fatal cocaine overdose pushed him to quit drugs cold turkey.

After cleaning himself up, Alexakis briefly attended UCLA film school. While living in Los Angeles, he organized a band called Shakin' Brave. Shakin' Brave featured a rather rough rock sound, but never really rose above the sea of music in Southern California. Generally frustrated with the music scene in LA, Alexakis and his first wife Anita relocated to San Francisco.

While living in San Francisco, Alexakis stumbled upon a genre of music known as "cow-punk". The sound meshed together the two prevalent forms of music with which he grew up - Country and straight-ahead Rock-n-Roll. Inspired, Alexakis established Shindig Records. Much of this period is explicitly detailed in the album, Deep In the Heart of the Beast In the Sun, which was originally intended as a solo album but gradually developed into a group project under the name Colorfinger.

In 1992, within a single month, Shindig went bankrupt, Colorfinger disbanded, and Alexakis' girlfriend Jenny became pregnant. Seeking a change of scenery, Alexakis moved to Portland, Oregon. There, he married his girlfriend and had a daughter. Though less directly biographical, Everclear's second album, Sparkle & Fade, deals deeply with the themes of escape and redemption that pervaded his life upon leaving San Francisco.

The instability and personal turmoil Alexakis went through left him with a wide breadth of subject matter for his songs. "Father of Mine" and "Why I Don't Believe in God" described his difficult youth. "Heroin Girl" and "Color Pit" touched upon his drug addictions.

In 2000, Alexakis testified before Congress in support of HR 1488, the Compassion for Children and Child Support Enforcement Act. He has also taped PSA's for the Office of National Drug Control Policy.

Alexakis has also been politically active. He was a delegate for the 2004 Democratic National Convention representing Portland's 3rd congressional district after campaigning for John Edwards during the 2004 Democratic Presidential primaries. He and the new Everclear recorded the Woody Guthrie standard This Land Is Your Land, which Alexakis performed at several political events.

On January 4th, 2005, Alexakis filed for Chapter 11 bankruptcy in United States Bankruptcy Court, Central District of California. According to the filing, Alexakis owes a federal tax bill for the years 1999, 2001 and 2002 of $2.75 million, as well as nearly $230,000 to the Oregon Department of Revenue and more than $120,000 in credit card debt spread over several accounts.