The name of their first full-length recording To Sir With Hate was a play on the theme song from the British school film, To Sir With Love, performed by Lulu. A song from this LP, "The Fairview Mall Story" was based on true events concerning media publication of the names of men arrested after being entrapped by police and was instrumental in paving the way for the emergence of the queercore scene. Their video for the song, directed by indie feature film director Steven Rumbelow, involved 50's images of men cruising in their new cars, shopping malls, and car crashes, was intercut with the band and go-go dancer Bruce La Bruce. A video for the song "Where Are they Now?" was also made, directed by Marc DeGuerre.
Their live shows often included films played overtop of the band and a 'go-go' boy dancing. They were frequently accompanied by guest musicians who played instruments as varied as saxophone, trumpet, flute, or violin.
Independent-minded, they released their recordings, including their second full length recording All-Time Queen Of The World, themselves. A video for the song "Like This " from the album was directed by Bruce LaBruce with Fifth Column. The band also appeared on a number of compilations.
In 1992 they released a single, "All Women Are Bitches", on the independent record label K Records. Despite being controversial and receiving little airplay, the recording was reviewed by Everett True and voted "Single Of The Week" in the UK music publication Melody Maker. This song was included as well on their last full-length recording, 36-C, also on K Records. The band's last release was in 2002, on the Kill Rock Stars compilation, Fields And Streams.
The band performs live in the film named for them, Fifth Column at the Funnel, directed by Toronto experimental filmmaker John Porter. All of the members of the most recent line-up, and some previous members, appear in the G.B. Jones' movie The Yo-Yo Gang for which the band recorded the theme song.
In 2004 the song "All Women Are Bitches" was covered and re-imagined by the band Lesbians On Ecstasy on their self-titled debut album, Lesbians On Ecstasy, as "Bitchsy"; in 2005, it was remixed and sampled along with "Bitchsy" by Kids on TV for the compilation album Giggles In The Dark.
Band members have performed with other groups as well. Caroline Azar has recorded with Kickstand from New York, Shadowy Men on a Shadowy Planet, Greek Buck and Hidden Cameras from Toronto. Beverly Breckenridge was also a member of Phono-Comb. G.B. Jones has recorded with the Italian dark ambient group Mariae Nascenti, and prior to her involvement with Fifth Column, was part of the synth punk band Bunny and the Lakers. She now performs with Opera Arcana.