Englehart dropped out of the American Academy of Art in 1967 to join the staff of Chicago Today, where he published his first editorial cartoons. In 1972, he returned to Fort Wayne to start a small commercial art studio and work as a freelance artist for The Journal-Gazette. Influences included Pat Oliphant, Wayne Stayskal, Mike Peters, Jeff MacNelly, Doug Marlette, and Jim Borgman. From 1975 to 1980, he served as editorial cartoonist for the Journal-Herald in Dayton, Ohio. He spent the next 35 years of his career as the first full-time editorial cartoonist for the Hartford Courant from 15 December 1980 until the end of 2015, when he accepted a voluntary buyout plan. Englehart's cartoons have appeared in The New York Times, USA Today, Time, Newsweek, Sports Illustrated, Playboy, and Hustler.
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