"Stupid Boy"
Single by Cassadee Pope
from the album The Complete Season 3 Collection
Released	10 December 2012 (2012-12-10)
Format	digital download
Recorded	2012
Genre	Country
Length	3:38
Label	Universal

"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.

Urban told Billboard that he recorded "Stupid Boy" at the suggestion of his wife, actress Nicole Kidman. He also noted how the song's subject matter contrasted with the more up-tempo love song "Once in a Lifetime," the album's first single, saying that the two songs were "yin and yang."Sarah Buxton, who co-wrote the song, recorded a version before Urban did. This version was included on a 2007 extended play entitled Almost My Record as well as Buxton's 2010 self-titled album.

Tamara Conniff and Ray Waddell of Billboard described the song as "a ballad on how men foolishly break the hearts of the women they love."Associated Press reviewer Michael McCall called it "a funky, witty take on a guy who can't appreciate how good he has it."

In 2008, the song won Urban a Grammy Award for Best Male Country Vocal Performance.

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Wikipedia