Before he worked at CNN, or was hailed by GQ as "the realest man" in fake news, or reported from Afghanistan and Iraq for ABC News, his career in journalism started in print. In the '90s, Jake Tapper was working as a freelance writer for a number of publications, including The Washington Post, Entertainment Weekly, and Moment. In his own words, he worked "literally anywhere that [he] could get a byline" (via The New Republic). Before that, Tapper wanted to be a cartoonist.

In fact, he created caricatures and illustrations for The Washington Post and Los Angeles Times, even writing a comic strip called "Capitol Hell" that appeared in Roll Call between 1994 and 2003 (via Roll Call). This passion followed a comic Tapper submitted to his high school's senior yearbook that, when folded in a specific way, revealed male genitalia; a prank that earned him a suspension and community service (via Business Insider). This might not come as much of a surprise to critics of Tapper, however, given his only Politifact fact check that hasn't been deemed either true or mostly true was regarding the comic book origin story of DC Comics' Joker (via Politifact). 

Tapper has since channeled those creative skills into book writing. His second novel is due out in May 2021 and his non-fiction book The Outpost: An Untold Story of American Valor, is now a major motion picture available to stream on Netflix (via Twitter).