Bailey then wrote the film "A Boy's Life" (2003), which documents two years in the life of a boy from Eupora, Mississippi, and his interaction with social services. In 2007, he cowrote (with Jack Youngelson) the film "Ghosts of Abu Ghraib", "an examination of the prisoner abuse scandal involving U.S. soldiers and detainees at Iraq's Abu Ghraib prison in the fall of 2003," which was nominated for six Primetime Emmys, one of which it won—best nonfiction special. Following those films, Bailey wrote two documentary shorts for HBO: "Thank You, Mr. President: Helen Thomas at the White House" (2008) and "The Fence" (2010), which "examines the construction of the seven-hundred-mile fence along the . . . border between Mexico and the United States." "The Fence" had its premiere at the Sundance Film Festival. Bailey also wrote the 2012 film "Ethel", which "chronicles the life of Ethel Skakel Kennedy." Ethel was nominated for five Primetime Emmys, including one for Bailey (outstanding writing for nonfiction programming). Bailey was also awarded the Humanitas Prize for his work on the film.