"Little Miss Obsessive" is a song recorded by American singer Ashlee Simpson for her third studio album, Bittersweet World (2008). It features uncredited guest vocals from Tom Higginson, the lead singer of the Plain White T's. The song was written by Simpson, Jim Beanz, Victor Valentine and Karl Berringer. "Little Miss Obsessive" was produced by Jack Joseph Puig and Berringer, with vocal production by Beanz. The song was released as the "first official single" from Bittersweet World on March 11, 2008, following the commercial disappointment of its predecessor, "Outta My Head (Ay Ya Ya)".