Cluck began performing her songs publicly in New York City in 2000. She self-released her first solo album, "Diane Cluck", that same year. By 2001 she was appearing regularly at the SideWalk Cafe in New York's Lower East Side, a venue that has featured such artists as Jeffrey Lewis, Regina Spektor, and Kimya Dawson. Massachusetts-based record label Important Records distributed Cluck's second and third albums, "Macy's Day Bird" in 2001 and "Black With Green Leaves" in 2002. Also in 2002, her song "Monte Carlo" was included in a compilation of New York City Anti-folk music, "Anti-folk Vol. 1", released by British label Rough Trade Records.