James was born in Farmington Hills, Michigan, the son of Edie, an art teacher, and Robert Wolk, a show store owner. His family is Jewish, and James was raised in Reform Judaism. During his teenage years, James worked as an emcee at Bar and Bat Mitzvahs. He graduated from North Farmington High School in 2003, and from the University of Michigan School of Music, Theatre and Dance in 2007.