Bentley came out the blocks flying with his debut single in 2003 What Was I Thinkin becoming a Number 1 song on the Billboard Hot Country Songs. Operating within the country lane but with a music palette that pleasingly embraces a broader rock and pop sound, Bentleys studio albums have accounted for 25 singles on the Hot Country Songs and Country Airplay charts, of which 17 have reached Number one, and seven more have reached the top 5.

On 1 October 2005 Bentley was invited to be a member of the Grand Ole Oprey; he was the third youngest member after Carrie Underwood and Josh Turner.