Hale first obtained for his Screen Actors Guild card when he appeared in a commercial for MCI Inc., though it never aired. He made minor guest appearances in TV shows such as Dawson's Creek, The Sopranos and Sex and the City. He is often recognized for his role in the famous Volkswagen television commercial aired in 1999, in which he danced to the song "Mr. Roboto", which was later spoofed on Fox sitcom Arrested Development.

From 2003 to 2006, and returning to the role in 2013, Hale found success in television when he was cast as Byron "Buster" Bluth, the hapless, neurotic son with "mother issues" on Arrested Development.

In March 2006, Hale was cast in a co-starring role as the video store owner Simon in the NBC sitcom Andy Barker P.I., starring Andy Richter and co-created by Conan O'Brien. He was the voice of “Furlough" in The Tale of Despereaux, an animated children's film released in 2008. Hale had a recurring role as Emmett on Chuck, beginning in October 2008 and ending with the character's murder in January 2010. He joined the cast of Numb3rs in 2009, in the recurring role of Professor Russell Lazlo.

In 2012, Hale was cast in the HBO comedy Veep as Gary Walsh, the personal assistant to Vice President Selina Meyer (portrayed by Julia Louis-Dreyfus). On September 22, 2013, Hale won a Primetime Emmy Award for Outstanding Supporting Actor in a Comedy Series for his work in the show's second season. This was his first major award. He earned his second nomination in 2014, but lost the award to Ty Burrell. However, Hale won his second Primetime Emmy Award with his third nomination in 2015, in the same ceremony where Veep won its first Primetime Emmy Award for Outstanding Comedy Series.

In 2017, Hale hosted the 9th Annual Shorty Awards at the PlayStation Theater in New York City. The next year, Hale began portraying Jerome Squalor on the second season of the Netflix comedy/drama series A Series of Unfortunate Events.

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