Bailey was born in the vibrant city of Chicago, but his life took a dramatic turn when his parents got divorced at a young age, prompting him to relocate to Florida. This significant event had a profound impact on his life, shaping him into the person he is today.
He then went on to attend Duke University, where he earned a football scholarship and majored in Psychology. This academic achievement was a testament to his hard work and dedication.
After completing his education, Bailey moved to Los Angeles to pursue his childhood dream of acting. He further honed his craft by undergoing a training stint in London at the prestigious LAMDA.
His breakthrough in the film industry came with Adam Shankman's "Cosmo's Tale" in 1998, which premiered at both the Sundance and Cannes film festivals. This initial success paved the way for his future endeavors.
Bailey's television career flourished, starting with his role in "Buffy, the Vampire Slayer." He then went on to work with Oscar-winning directors and actors in "Saving Grace" and "Damages," showcasing his versatility as an actor.
One of his most critically acclaimed performances was in "Longmire," which solidified his position as a talented actor in the industry. He has since starred in various projects, including "Batman V Superman," "Chicago PD," "Grimm," "24: Legacy," "Twin Peaks," and "Queen of the South."
Recently, Bailey received a nomination for Best Lead Actor for his performance in "Far Haven," a testament to his exceptional acting skills. He is currently working on the upcoming film "Homestead," set to be released in 2024.
Bailey resides in North Carolina with his loving wife and three children, enjoying a peaceful life away from the spotlight.