She first entered the pop market with the song "I.M. Me" while still using her given name. Her first album, Everything I Wished For, was released by the Free Falls record label in 2002 after two years of recording. The album reached #45 on the Billboard Top Independent Albums chart. When Cleary signed with Jive Records in summer 2002, they asked to change her name because they already had a Britney on their roster. Her eponymous debut album was released a year later.
She appeared on a Nickelodeon Kids' Choice Awards record in 2003, with her single "1, 2, 3". She also performed on Nickelodeon's All That. Cleary also did a version of "Summertime Guys", used on the Kim Possible soundtrack. Her song "Hated" was on the Mean Girls film soundtrack.
- Everything I Wished For (2002)
- Nikki Cleary (2003)