Born in Los Angeles and raised in Orange County, Drew Conrad began playing music at the age of four. Initially starting on the piano, he quickly gained interest in the guitar. By age ten, he discovered his most natural talent - singing. At twelve, he fronted his first band along with brother Erich on guitar.

By age seventeen, Drew again formed a band with Erich. The music was melodic and melancholic, with Erich composing the music and Drew assuming lyrical duties. The two played as a duo for a couple of years, gigging throughout Orange County at coffeehouses and art openings. Adding bass and drums, as well as additional vocals and keyboards, the band started playing bars and clubs. In 1995, Erich departed to pursue a doctoral degree. Drew graduated college with a degree in English Literature and determined to focus exclusively on the band, known as Willoughby Station.

After playing alongside national touring artists such as The Posies, Damien Jurado, and The Mother Hips at some of Orange County's best clubs, the group saw fit to take the music up to L.A. in early 2001. Soon thereafter they found themselves playing numerous shows at The Knitting Factory, The Roxy, The Mint, and other well-known L.A. venues in support of national and international touring acts. In early 2003, the band restructured itself significantly, essentially closing the Willoughby Station era. Drew, along with Willoughby bassist Mark Zelen, teamed up with drummer Scotland Stephenson and formed ALSO.