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Payne started drawing cartoons as he earned a history degree at Princeton University for two student publications, The Daily Princetonian and The Nassau Weekly. After graduating, Henry began his professional cartoonist career with the Charleston Daily Mail (Charleston, West Virginia) from 1984 to 1986. From 1986 to 1999, he worked at the Scripps Howard News Service in Washington D.C. on its cartoon wire as an editor and an editorial cartoonist.
In 1999, Henry joined the Detroit News (Detroit, Michigan) as an editorial cartoonist and an editorial writer. Due to budget cutbacks at the Detroit News, Payne was removed as a local editorial cartoonist in October 2013, but still maintained work on the editorial pages. By November 2013, he became the News' auto critic.
Payne worked as an editor for the Detroit News' Politics blog, which featured up to 20 Michigan-based commentary and opinion writers. He founded and edited The Michigan View.com for the Detroit News, an 2010-2013 online opinion site, which had up to 30 writers working for the web page.
When with Scripps Howard, Payne's editorial cartoons were syndicated by the Associated Press. By the times he was with the Detroit News, his cartoons were syndicated by the United Media Enterprises through its United Feature Syndicate. After the end of Henry's time as editorial cartoonist with the News, his nationally-oriented editorial cartoons continued to be syndicated by Universal Uclick (who took over for United Media in 2010), and often showed up in the News as well. As of 2018, Payne's editorial cartoons are still syndicated by Universal Uclick.
Payne has also written for National Review, The New York Post, Scripps Howard News Service, The Wall Street Journal, and the Weekly Standard.
Princeton University ? to 1984
Notes: Degree in history. Did cartooning for the student publications, The Daily Princetonian and The Nassau Weekly.