"Careless" was the second single released by Australian rock group Paul Kelly and the Messengers from their 1989 studio album, So Much Water So Close to Home. The song was written by Kelly and co-produced with Scott Litt. The single was released in November 1989 on the Mushroom Records label. It reached the Top 100 on the Australian Kent Music Report Singles Chart. 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).

Paul Kelly had formed Paul Kelly and the Coloured Girls in 1985, named from a line in Lou Reed's "Walk on the Wild Side". The Coloured Girls were Michael Barclay on drums and backing vocals, Peter Bull on keyboards, Steve Connolly on lead guitar and Jon Schofield on bass guitar. For international releases from 1987 they used the name Paul Kelly and the Messengers to avoid possible racist interpretations. 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. The album peaked at No. 10 on the ARIA Albums Chart. It was recorded in the United States with Scott Litt, best known for his work with R.E.M., co-producing with Kelly. Litt had re-mixed some of Paul Kelly and the Coloured Girls' earlier tracks for their US releases as by Paul Kelly and the Messengers.So Much Water So Close to Home was released on Mushroom/White Records in Australia and A&M Records in the US and Europe. "Sweet Guy" was the first single from the album and peaked at number 53 on the ARIA singles chart. "Careless" was the second single from the album, but failed to chart on the ARIA top 100 singles chart. It peaked at number 92, however, on the Kent Music Report chart

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