Sad Like Crazy formed in 1997 when Gram LeBron, Trey Pool, and Mari Chow began to collaborate in Houston, TX. LeBron and Pool had been reworking some songs from their previous band, Trompedo, and Chow fit perfectly into the mix. A quick musical camaraderie took form with LeBron on drums and Pool and Chow on guitar and vocals. Bassist Thane Matcek joined the group soon after, forming a quartet. They soon recorded a six-song self-released cassette, C'mon, Music. 1999 saw the release of the My Heart Is a Hobo 11-song cassette on Spare Change Records. Still in 1999, LeBron left the band when he moved to San Francisco, where he continued work in his other band, Schrasj, and his a solo project, Golden Gram. Also in 1999, Pool and Chow married each other. The band eventually settled on Piam Oskouie as LeBron's replacement on drums. The new lineup recorded nearly 100 songs between 1999-2000. The 2001 release of Love Songs to Death on Ojet signaled as part one of Sad Like Crazy's history, chronicling the brightest moments of their first four years of existence.