Easton broke on the scene in 2009 with not one, but two, No. 1 singles, "A Little More Country Than That" and "Roll With It," and a Top 15 hit, "I Can't Love You Back," the country music world was put on notice. He became the first country male artist in 17 years to have his first two consecutive singles reach No. 1. Billboard named Easton the Top New Country Artist of 2010 and named "Roll With It" the No. 6 Hot Country Song of the Year. He was ranked No. 9 on Billboard's list of Top Country Artists-Male, listed between Blake Shelton and Tim McGraw.