Bennett has been the editorial cartoonist for The Christian Science Monitor since 1998 and, while there, he was a Pulitzer finalist five consecutive years, winning it in 2002. He has also earned just about every other editorial cartoon award there is, including the Robert F. Kennedy Journalism Award, the John Fischetti Editorial Cartoon Competition, the Overseas Press Club's Thomas Nast Award, the National Headliner Award, the Society of Professional Journalists' Sigma Delta Chi Award, the National Journalism Award from the Scripps Howard Foundation, and the National Cartoonists Society Division Award for Best Editorial Cartoons. Bennett was also named Editorial Cartoonist of the Year by Editor & Publisher magazine in 2001.