During this time, Simon met Fox Feature Syndicate comics artist Jack Kirby, with whom he would soon have a storied collaboration lasting a decade-and-a-half. Speaking at a 1998 Comic-Con International panel in San Diego, California, Simon recounted the meeting:
with the comic book industry beset by self-imposed censorship, negative publicity, and a slump in sales. Simon turned primarily to [[advertising]] and [[commercial art]], while dipping back into comics on occasion. He created, edited and produced material for the humor magazine ''Sick'', a competitor of ''[[Mad (magazine)|Mad]]'' magazine, for over a decade. The Simon & Kirby team reunited briefly in 1959 with Simon writing and collaborating on art for [[Archie Comics]], where the duo updated the superhero the [[The Shield (Archie Comics)|Shield]] in the two-issue ''The Double Life of Private Strong'' (June-Aug. 1959), and Simon created the superhero [[The Fly (Archie Comics)|Fly]]; they went on to collaborate on the first two issues of ''The Adventures of the Fly'' (Aug.-Sept. 1959) and Simon and other artists including [[Al Williamson]], [[Jack Davis (cartoonist)|Jack Davis]], [[Carl Burgos]] and others did four issues before Simon moved on. Simon & Kirby again reteamed for [[Harvey Comics]] in 1966, updating Fighting American for a single issue (Oct. 1966). Simon, as owner, packager, and editor, also helped launch Harvey's original superhero line, with ''Unearthly Spectaculars'' #1-3 (Oct. 1965 - March 1967) and ''Double-Dare Adventures'' #1-2 (Dec. 1966 - March 1967), the latter of which introduced the influential writer-artist [[Jim Steranko]] to comics.
In 1968, Simon created the two-issue DC Comics series
Brother Power the Geek, about a mannequin given a semblance of life who wanders philosophically through 1960s hippie culture; Al Bare provided some of the art. Simon and artist Jerry Grandenetti then created DC's four-issue
Prez (Sept. 1973 - March 1974), about America's first teen-age president.
Simon & Kirby teamed one last time later that year, with Simon writing the first issue (Winter 1974) of a six-issue new incarnation of the Sandman. Simon and Grandenetti then created the Boy Millionaires in the DC try-out series
1st Issue Special #2 (May 1975), and the freakish Outsiders in
1st Issue Special #10 (Jan. 1976).