Roof was born at an Air Force hospital in Tampa, Florida to Michael Roof, Sr. and Jean (Tillet). Roof had two brothers, Derek and Donny; and two sisters, Megan and Kim.
Roof toured the nation's comedy clubs with a stage name of "Chicken." He was especially popular in college town comedy clubs such as Deja Vu in Columbia Missouri.
In 2000, he had a central part in the WB Network sketch comedy TV series Hype, but it was canceled after its first season. After Hype, Roof moved to Hollywood, California to pursue a film career.
He landed a number of film roles in big-budget Hollywood productions. Some of these include the role of Private Mike Maddox of the US Rangers in Black Hawk Down, the comedic character of Dil Driscoll in The Dukes of Hazzard, and National Security Agency Agent Toby Lee Shavers in xXx and its sequel xXx: State of the Union.
Roof's role as NSA Agent Shavers in xXx and xXx: State of the Union are perhaps Roof's most recognized.
In 2006, Roof was given his own Spike Channel reality TV show, Raising the Roofs. The program, which ran for six episodes, followed the misadventures of his self-described "Florida cracker" dad, Michael, Sr., and his uncle, while they visited Roof at his home in Hollywood.
After "Raising the Roofs" was cancelled, Roof moved to Georgia with his wife, Megan (Bowen), and their three sons, Chase, Jackson, and Sean.