Hemingway began working in the industry on Tom Fontana’s HBO prison drama Oz as an assistant director. He later worked with Fontana on The Jury. He was the first assistant director on the film Freedomland in 2006 which was written by The Wire writer Richard Price and featured several cast members from that show alongside Samuel L. Jackson. He first worked with Jackson as assistant director on the 2002 film Changing Lanes. He first worked with director/producer Joe Chappelle on the 2000 film Takedown and has since collaborated with him on The Wire and CSI: NY.

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 Rick McCallum and Chas. Floyd Johnson, was released.

Hemingway identifies as gay, stating that he had known his entire life. He and actor Steven Norfleet started dating in 2014, after being introduced through a mutual friend. They got engaged in June 2018 and married in September 2019.

In 2020, Anthony Hemingway signed a deal with 20th Television to produce and direct its own projects.