Starting out in Wellington in the late 90's. Bret and Jemaine were flatmates back then and both dropped out of university. Bret "dribbled on for ages" studying English and music at Victoria University while Jemaine attempted to study film and theatre but eventually gave that up.
In 1998, they were sharing an old villa in Mt Victoria and performing in local productions around town. Jemaine was writing and performing in 'Skitz' and also teamed up with fellow comedian, Taika Cohen (Taika Waititi), as 'Humourbeasts', a comedy production which won the Billy T comedy award in 1999.
Hurt Feelings debuted in the Official New Zealand Top 40 Singles on 2 November 2009. It has been in the Top 40 Singles for one week with a highest position of #36. There are three songs by Flight Of The Conchords in the Top 40 Singles with one reaching Number One.