James Bennett began studying art at Bucks County Community College in Pennsylvania. His professional career as an illustrator started soon after receiving recognition from the Society of Illustrators and RSVP as a scholarship student at the School of Visual Arts in New York City.

Bennett's conceptually humorous illustrations have since appeared as covers and interior pieces for The New York Times, Sports Illustrated, Business Week, TIME, MAD, The L.A. Times, Golf Digest, Maxim, and Readers Digest among others. He has produced art for RCA Records, American Express, Paramount Pictures, Citibank, Hasbro, and Milton Bradley.

Bennett's awards include the prestigious Hamilton King Award, which acknowledges an illustrator's outstanding body of work represented by the "Best Illustration of the Year," the Stevan Dohanos Award from The Society of Illustrators in NYC. The "Creative Show" in San Diego which recognizes the best in advertising for the year, awarded him a gold medal, and he has won both gold and silver medals from the Society of Illustrators Annual Shows in New York and Los Angeles. He has been featured in magazines such as Communication Arts and Fantasy Art from China.