In 2000 Madeline began performing her songs in Athens, Georgia at the age of 15. Over the next couple of years, Madeline worked on a full length album and fronted the locally successful psychedelic pop band, The Sugar Shakers. In 2002 Madeline self-released her album Kissing & Dancing. In 2003 the record was re-released by Plan-It-X records. That year, Madeline went on her first big tour, accompanied by Zumm Zumm.
