Jaffee first appeared in "Mad" in 1955, one issue after its transformation from comic book format to magazine. When editor Harvey Kurtzman left in a dispute three issues later, Jaffee went with Kurtzman. Jaffee contributed to Kurtzman's first two post-"Mad" publishing efforts, "Trump" and the creator-owned "Humbug". In 2008, the first full reprint of "Humbug" was published as a two-volume set by Fantagraphics; the set includes a newly commissioned cover illustration by Jaffee, and a co-interview with Jaffee and Arnold Roth.