Bittersweet World is the third studio album by American recording artist Ashlee Simpson. It was first released in Australia on April 19, 2008, with a release soon after in the United States on April 22, 2008 via Geffen Records. The album’s lead single, “Outta My Head (Ay Ya Ya)” was released on December 11th, 2007, and became her first single to not appear on the Billboard Hot 100 chart in the United States. “Little Miss Obsessive” was released as the second and final single on March 11, 2008, featuring guest vocals from Plain White T’s frontman Tom Higgenson. The song charted at #96 on the Billboard Hot 100.