Born and raised in Four Oaks, North Carolina Bailey began playing mandolin at 11 years old. He later would switch over to guitar at the age of 18. Bailey spent two and half years with the GrassCats before coming to Sideline. Bailey is also a graduate of The University of North Carolina at Greensboro and will continue his education in Occupational Therapy. When Bailey is not on the road or playing music he enjoys spending time with his friends and loved ones, reading and playing with his two dogs Harvey and Molly. Music has always been a cornerstone of Bailey's life and he looks forward to continuing that with Sideline.