Willingham graduated from Texas Christian University with a BFA in Theater Performance. Following his work at Funimation (which included series such as Dragon Ball Z and Full Metal Alchemist), he moved to LA and later married fellow Funimation voice actress Laura Bailey.

Since then, he has lent his voice to several animes, video games, and television shows, as well as acting in some shows, including Street Fighter IV, Cold Case, Nip/Tuck, Call of Duty: Black Ops, Catherine, and Halo 4. Willingham again took part in the Dragon Ball series with Dragon Ball: Raging Blast 2 in 2010.