Claim: Keith Urban sang a single.

`` Stupid Boy '' is a song that was written by Dave Berg , Deanna Bryant and Sarah Buxton . First recorded by Sarah Buxton , it was later recorded by Australian country music singer Keith Urban on his 2006 album Love , Pain & the Whole Crazy Thing , from which it was released as that album 's second single in December 2006 . A year after its release , the song won Urban a Grammy Award for Best Male Country Vocal Performance .