After graduating, Brad signed a songwriting contract with EMI Music Publishing. His debut as a singer was with the label Arista Nashville. The song was "Who Needs Pictures" (released February 22, 1999). His first No. 1 hit came that December, with "He Didn't Have To Be."

In 2000, Brad won the Country Music Association's (CMA) Horizon Award and the Academy of Country Music's best new male vocalist trophy. He received his first Grammy Award nomination a year later. In 2002, he won the CMA Music Video of the Year for "I'm Gonna Miss Her (The Fishin' Song)." He made his debut on the Grand Ole Opry on May 28, 1999, and after 40 appearances, was inducted into the Opry on February 17, 2001.

Brad released his third album, Mud on the Tires (2003), following Who Needs Pictures and Part II. The new album features the hit song "Celebrity," which parodies reality shows such as Fear Factor and famous people such as Jason Alexander (who is also featured in the music video); and the title track (a No. 1 hit in January 2005).

Brad is married to actress Kimberly Williams. They live in Franklin, Tennessee.

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