Bailey was born in Chicago but moved to Florida after his parents divorced at a young age. He attended Duke University on a football scholarship and majored in Psychology. After graduation, Bailey moved to LA to pursue his boyhood dream of acting which encompassed a training stint in London (LAMDA). His first film break came in Adam Shankman's Cosmo's Tale (1998), which screened at both Sundance and Cannes. Bailey's career blossomed in television starting with Buffy, the Vampire Slayer then working with Oscar-winners in Saving Grace and Damages before his own critically acclaimed performance in Longmire. Bailey has starred in various projects since including Batman V Superman, Chicago PD, Grimm, 24: Legacy, Twin Peaks and Queen of the South. He was recently nominated for Best Lead Actor for his performance in Far Haven and is currently shooting Homestead (2024). Bailey resides in North Carolina with his wife and three children.