Born January 20, 1958 in Clinton, South Carolina. The son of a career army officer, Bennett led a nomadic life, attending ten different schools before graduating in 1976 from S. R. Butler High School in Huntsville, Alabama.
Served as editorial cartoonist for his college paper and managing editor of the alternative student newspaper while attending the University of North Alabama, where he graduated in 1980 with degrees in art and history.
After working briefly as a staff artist for the Pittsburgh Post-Gazette and The Fayetteville (NC) Times, Bennett went on to serve as the editorial cartoonist for the St. Petersburg Times (1981-1994) and The Christian Science Monitor (1997-2007) before joining the staff of the Chattanooga Times Free Press in 2008.
A recipient of the 2002 Pulitzer Prize for Editorial Cartooning, Bennett has earned nearly every honor his profession has to offer including the Sigma Delta Chi Award (2001, 2017, 2019), the Overseas Press Club Award (2005, 2007, 2017), the National Headliner Award (1999, 2000, 2004, 2016), the Robert F. Kennedy Journalism Award (2007), the Berryman Award (2014), the John Fischetti Award (2001, 2005), the Scripps Howard Foundation National Journalism Award (2002), the Grambs Aronson Award for Cartoons (2013), the United Nations/Ranan Lurie Political Cartoon Award (2011) and the National Cartoonists Society's Award for Editorial Cartoons (2002, 2017).
Past President of the Association of American Editorial Cartoonists, Bennett is the husband of artist Cindy Procious and the father of Matt, Ben and Sarah. His work is distributed internationally by The Washington Post Writers Group.