Judge Jackson was born in 1955 in Orangeburg, South Carolina to Sue Gatlin Jackson and the late James B. Jackson, Sr. He is married to the former Cynthia Martin of Salem, Virginia. and they have two children, Benjamin and Katherine.

Judge Jackson is a 1977 graduate of Emory & Henry College, Emory, Virginia, and a 1980 University of South Carolina School of Law. Upon graduating from law school, he joined the law firm of the late Thomas O. Lawton, Jr., in Allendale, South Carolina where he practiced until January 1982. In February 1982, Judge Jackson opened his own law firm in Orangeburg, South Carolina where he practiced until December 1987. He also served as a part-time Public Defender for Orangeburg County form 1984 through 1987. In January 1988, he began full time employment as Assistant Solicitor for the 1st Judicial Circuit where he worked until December 1989. In January 1990, he became a partner with the firm of Yarborough, Hutto and Jackson where he practiced until 2007. In October 2007, Judge Jackson joined the firm of Nester and Jackson in Santee, South Carolina as a partner, where he continues to practice.

He has been an active member of the Orangeburg Kiwanis Club since 1982 and is a past president of the Orangeburg County Bar Association.

His hobbies include reading and playing golf.