One of Cannon’s first notable compositions was “I Love the Way You Love Me”, a Number One hit for John Michael Montgomery in 1993, which Cannon co-wrote with Victoria Shaw. This song also won the Song of the Year award at the Academy of Country Music awards, which is awarded to songwriters. From there, Cannon began working primarily for Toby Keith, including “Me Too”, “Dream Walkin'”, “We Were in Love”, “Getcha Some”, “If a Man Answers” and “When Love Fades” in the late 1990s, “How Do You Like Me Now?!” in 2000, and “American Soldier” in 2003-2004. “How Do You Like Me Now?!” was also the Number One country song of the year according to the Billboard Year-End charts. Both it and “I Love the Way You Love Me” earned Eight-Million-Air awards from Broadcast Music Incorporated for receiving eight million spins at radio. Cannon also self-released two albums: God Shaped Hole and Love and Money in 2006 and 2008, respectively.