"Careless" is a song by Australian rock group Paul Kelly and the Messengers, released in October 1989 as the second single from their 1989 studio album, So Much Water So Close to Home.

[3] The song was later covered by Renée Geyer on Difficult Woman (1994), Angie Hart on Women at the Well (2002), and Ozi Batla (MC for The Herd) on Before Too Long (2010).

[4][6] In August 1989 after two albums the group issued, So Much Water So Close to Home under the band name Paul Kelly and the Messengers in all markets.

[9] It peaked at number 92, however, on the Kent Music Report chart[10] The video for "Careless" was directed by Kimble Rendall (XL Capris, Hoodoo Gurus, The Angels, Cold Chisel)[11][12][13] and features Kelly and his band performing the song around an open fire, interdispersed with film from a wedding video.

[15] In 2004 Paul Kelly and the Boon Companions performed the track for the DVD, Ways & Means, in the section subtitled Live in Boston.

[12] Since its release, it has been covered by Renée Geyer on Difficult Woman (1994) – Kelly produced her album, also wrote the title song, "Sweet Guy" and "Foggy Highway".

Ozi Batla (MC for The Herd) sang both "Careless" and "Sydney From a 727" for the Kelly tribute show and related album, Before Too Long (2010).

[12] "Special Treatment" is a protest song that Kelly wrote highlighting the oppression of Australian Aborigines.