Jaffee first appeared in Mad in 1955, shortly after its transformation from comic book format to magazine. When editor Harvey Kurtzman left in a dispute, 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.
After Humbug folded in 1958, Jaffee brought his unpublished material to Mad, which bought the work. "Bill Gaines took out every Trump and Humbug," remembered Jaffee, "called me into his office, sat me down on the couch next to him, and went over every issue and said "Which is yours?" And as he came to each one, when he saw my stuff, he OK'd to hire me."