"Sure Be Cool If You Did" was praised by
Entertainment Weekly, which gave it an A− and called it "ludicrously catchy". Billy Dukes of
Taste of Country gave the song three stars out of five, calling it "comparatively ordinary next to catalog hits like '
She Wouldn't Be Gone' and the infectious '
Honey Bee and writing that "a break in the name of artistry would satisfy fans of his rowdier songs, while giving those who discovered him on TV something more nourishing to listen to." Matt Bjorke of
Roughstock gave the song three and a half stars out of five, saying that "the production of Scott Hendricks may not be as groundbreaking or as 'identifying' as say
Jay Joyce or
Joey Moi's productions are but the sound here is still likable - albeit a tad
MOR." Bob Paxman of
Country Weekly gave the song a C and compared the song's melody to that of an earlier Shelton single, "
Over". He felt that "Sure Be Cool If You Did" featured cliche lyrics but praised Shelton's vocal performance as "truly rich and expressive" while singling out "the searing guitar breaks" as "the most interesting components" of the song. Gary Graff of
The Oakland Press called the song "as polished and melodic as any pop hit". Chuck Dauphin of
Billboard wrote, "it’s not exactly the most well-written song of his career, but his vocal is very pleasing on the cut – as well as the arrangement." ==Commercial performance==