The band only took one year working on their debut album, Swan Songs. The other two years were spent looking for a company that wouldn't try to censor the album. They first signed a record contract with MySpace Records in 2005 but they left the label after the label tried to censor their first album. They also tried to sign with Interscope Records but they wouldn't publish the songs uncensored. They then signed a contract with A&M/Octone Records and Swan Songs was released on September 2, 2008 and reached #22 on the Billboard 200 in its first week of release, selling 21,000 copies; which was later on released in the United Kingdom on May 18, 2009 with two bonus tracks.
On June 23, 2009, Hollywood Undead released Swan Songs B-Sides EP through iTunes. The band released a CD/DVD set entitled Desperate Measures on November 10, 2009. The set includes a CD of previously unreleased six new songs, three of which are cover songs, as well a previously unreleased remix of Everywhere I Go, and six live recordings of songs from Swan Songs, and a DVD of a full live performance by the band. It peaked at number 29 on the Billboard 200.
In December 2009, the band won Best Crunk/Rock Rap Artist at the Rock on Request Awards.