Huskey was born in Charlotte, North Carolina, and did not meet his biological father until he was 17. He attended Charlotte Country Day School for the entirety of grade school, graduating in 1987. He attended University of North Carolina at Greensboro, graduating with a degree in English and minor in photography. Around this time he began to play in the band Bicycle Face.
He made some notable early television appearances in a series of commercials opposite Molly Erdman in a campaign for Sonic Drive-In. Both actors would later be fired from this role as the result of an Onion News Network veterans parody he wrote and performed. Huskey has appeared in commercials for Wendy's, and, in 2011, "The Swagger Wagon" ad campaign for the Toyota Sienna.
In 2014, Huskey co-wrote the film A Better You, with UCB co-founder Matt Walsh. Huskey starred in the film and Walsh directed.
