Written by Ben Folds to be the lead single off Whatever And Ever Amen, this piano-driven tune was based on the lacklustre slacker lifestyle the band encountered at the time in their North Carolina home base. Bassist Robert Sledge told Sodajerker On Songwriting podcast, "With 'The Battle Of Who Could Care Less,' that was about the attitude in Chapel Hill, like it's a competition who can be cooler and more indifferent. That was definitely a shared frustration between the band because like for me, I'm always striving to play really well and expand myself, but that's just not cool, at all."
The song achieved Ben Folds Five's joint highest UK chart position of #26 (along with "Brick"). It was helped by a comedic video directed by Norwood Cheek.
The Whatever and Ever Amen album title came from a line in this song.
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