For The Wire Hemingway served as the first assistant Director on several episodes in the first season and throughout the second and third season. He returned in 2006 as a Director for the seventh episode of the fourth season "Unto Others". Showrunner David Simon said that Hemingway's directing debut proved what they already knew, "that it was time." The experience has led to directing work on several other series for Hemingway.
In 2012, Hemingway's first feature film Red Tails, produced by George Lucas, was released.
