Cutcliffe was born and raised in Birmingham, Alabama, which played a formative role in his development as a football coach. He has two brothers (Charles "Paige" Cutcliffe, and Raymond Eugene "JR." Cutcliffe) and three sisters (Mary Marlyn Cutcliffe Sullivan, Margart Lynn Cutcliffe, and Elizabeth "Buff" Cutcliffe Easterly.) Cutcliffe attended Banks High School in Birmingham where he played football. He attended the University of Alabama where he worked as a student assistant on Bear Bryant's Alabama staff.