Penny Flanagan was one half of Australian folk band Club Hoy until the band's demise in 1993. Following the break-up, she embarked on a solo career, which, despite record company problems, saw her become one of the more successful Australian singer/songwriters of the mid-'90s.
In 1994, a year after the end of Club Hoy, Penny Flanagan's debut solo album Bravado appeared, featuring her backing band the New Moon. Its release had been preceded by the first single from the album, "Lap It Up," which had received significant airplay on Australian radio. The album itself was folk in nature, but ranged from country-influenced tracks, to straightforward pop tracks, and even to dance, thanks to a Boxcar-remixed version of "The Sky," which also became a radio hit. Bravado was poorly promoted by Flanagan's record company, and despite good reviews and the success of "Lap It Up," the album did not become widely successful.
Nearly two years of legal wranglings with her record company followed until Flanagan was released from her contract in 1996. Forming her own record label, Penny Dreadful, Flanagan recorded an acoustic set of songs, including some that had appeared on Bravado, and released this as Seven Flights Up in 1996. Praised by critics, this album did not succeed commercially, mainly due to the fact that it was only available by mail order for some considerable time after its release.
In 1999, Flanagan returned with a new album, Light Sleeper, her first album of entirely new material in five years.
Penny Flanagan is also a published author, with two novels and a number of short stories to her credit.