When I Was Cruel is the 19th studio album by English singer-songwriter Elvis Costello, released in the US by Island Records on 23 April 2002.

Although formally credited as solo Costello album, this was the first album to feature his new band, the Imposters featuring Steve Nieve on keyboards, Davey Faragher on bass guitar and Pete Thomas on drums.

Their only difference from his previous band, the Attractions (active 1977–87 and 1994–96), was Faragher replacing Bruce Thomas, with whom Costello had feuded.

[13] Japan also featured as a bonus track a cover of Charlie Chaplin's song "Smile", which was later released as a single.

The song also features Costello's penchant for multiple meanings, referencing the year 1945, .45 caliber pistols, and 45 rpm records.