James was born in St. Louis, Missouri and attended high school at Central Visual and Performing Arts High School. After graduating in 1990, he attended both the Center for Creative Studies in Detroit, Michigan and the University of Missouri in Columbia, Missouri before settling at the School of the Art Institute of Chicago. After three years at SAIC he graduated with a Bachelors degree in Fine Art in 1995.
James started tattooing while at the Art Institute in 1994. Self-taught, he worked on friends in his spare time while working coloring comic books. In 1996, answering an ad in the paper, James was hired at Milios Salon as a tattoo artist. While at Milios, he worked with Jason Leisge (now at Infinity Tattoo in Portland, Oregon) and then his brother Tim Kern. In 1999, he participated in a tattoo demonstration at University of Illionois-Chicago as part of a lecture series celebrating body art. After approximately three years at Milios, it was time for a change and James and Tim moved to No Hope No Fear (formerly owned and operated by David Kotker) in the Wicker Park neighborhood of Chicago.
His work has won numerous awards at tattoo conventions and has been published in many tattoo magazines, as well as feature articles in Tattoo Magazine (August 1998) and Skin Art #70, Tattoo Society #4, Skin and Ink, Tattoo Flash and (most recently) Northwest Tattoo Magazine- as well as magazines in Germany, France, Mexico and Japan.
In 2004, James self-published his book “Advanced cover-ups for tattooists” which is now out of print. A new edition of the book is in the works.