Born in West Point, NY into a military family, Hale was ultimately raised in Tallahassee, FL, where he spent his middle and high school years. After realizing he was more attuned to acting than sports, he joined the Young Actors Theatre and performed in a number of local productions, before earning a journalism degree from Samford University in Birmingham, AL. Even though he chose journalism as his fallback career, Hale still pursued his ambition of becoming an actor by moving to New York City and trying his hand there. While in Manhattan, he formed The Haven, an artistic group of Christians that met weekly, while also studying his craft at the prestigious theater company, The Barrow Group. Following an appearance in the sex comedy "Raging Hormones" (1999), Hale landed a nationally televised commercial for Volkswagen, where he famously sat in the driver's seat earnestly singing the Styx song "Mr. Roboto." Though the spot was his most famous, it was only one of many.While still living in New York, Hale began landing guest spots on a number of series shot in the area, including "Sex and the City" (HBO, 1998-2004), "The Sopranos" (HBO, 1999-2007) and "The $Treet" (2000-01). After playing a doctor in an episode of "Dawson's Creek" (The WB, 1998-2003), Hale landed the role of a lifetime on the cult favorite, "Arrested Development" (Fox, 2003-06), where he played Byron "Buster" Bluth, the youngest brother of the highly dysfunctional Bluth family. A professional student who idolizes his older brothers, Michael (Jason Bateman) and GOB (Will Arnett), Buster is immature, socially inept, and possesses an unhealthy, almost oedipal connection with his domineering mother, Lucille (Jessica Walter). But despite the show's rabid cult following and its popularity with critics, "Arrested Development" was ratings challenged and ultimately lasted only three seasons to the dismay of devoted fans. Over the course of the next several years, there was continual talk about the show moving to another network and even rumors of a possible movie being developed, though the process of writing a script for the big screen proved to be a long one. After a full cast reunion in 2011 for The New Yorker Festival, Netflix announced that it would produce 10 new episodes for release in 2013, with the intention of serving as a lead-in for a potential film. All original cast members, including Hale, were set to reprise their roles.Meanwhile, Hale was featured on the short-lived Pamela Anderson sitcom "Stacked" (Fox, 2005-06) and Andy Richter's "Andy Barker P.I." (NBC, 2007), and made the jump to features with supporting roles in "Stranger than Fiction" (2006) and "RV" (2006). From there, he had a recurring part on the geeky spy comedy "Chuck" (NBC, 2007-2012) during the second season, where he played the effeminate and abusive manager of Buy More. Following a supporting role in the romantic comedy "Because I Said So" (2007) and voice work as Furlough in "The Tale of Despereaux" (2008), Hale landed a slew of guest-starring roles on shows as varied as "ER" (NBC, 1994-2009), "Community" and "Justified". While he logged in episodes of "Royal Pains" (USA Network, 2009-16) and "Psych" (USA Network, 2006-2014), Hale returned to regular-series status on the political comedy "Veep" (HBO, 2012-), where he delivered a deftly comic turn as the sycophantic aide to an incompetent, gaffe-prone vice president (Julia Louis-Dreyfus). In 2013, Hale joined Netflix's resurrection of "Arrested Development" along with the rest of the cast. He also scored a pair of small but memorable film roles, a cameo as a bemused bus passenger in the teen-centric indie comedy-drama "The Kings of Summer" (2013) and an appearance as a hapless john busted by Melissa McCarthy's loud-mouthed Boston cop in the action comedy hit "The Heat" (2013). Later that year, he won his first-ever Emmy for his reliably hilarious role on "Veep," a win he repeated in 2015. He continued his side interest in voiceover work with a recurring role in the cult animated hit "Sanjay and Criag" (Nickelodeon 2013-). In 2015, he co-starred with Jesse Eisenberg, Kristen Stewart, and Connie Britton in action comedy "American Ultra" (2015).