"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.