and 1980s. During the 1980s, Orlando began teaching at the School of Visual Arts, continuing as an art instructor there for many years. In 1987, he created an illustration for the supplemental text piece from Watchmen #5, a page from the comic-within-the-comic, Tales of the Black Freighter. Orlando's contribution was designed as if it were a page from the fake title; the conceit being that Orlando had been the artist for a run of stories from the fictional Tales of the Black Freighter comic. Watchmen writer Alan Moore chose Orlando because he felt that if pirate stories were popular in the Watchmen universe, DC editor Julius Schwartz would have lured Orlando into drawing a pirate comic book. The comic-within-a-comic pages were credited to the fictitious artist "Walt Feinberg", and all art attributed to Feinberg was actually drawn by series-artist Dave Gibbons. The Orlando page was the only artwork for the series not by Gibbons. A limited series featuring The Phantom published by DC in 1988 was written by Peter David and drawn by Orlando and Dennis Janke. Orlando had a long working association with the prolific letterer Ben Oda, roughing out display lettering effects which Oda would finish. During the 1990s, Orlando was pleased to discover that designer-typographer Rick Spanier, working on a Macintosh computer, could create polished Oda-like finishes of Orlando's roughs. These Orlando-Spanier collaborations were printed in DC's Superman Style Guide and other DC style guides. Associate publisher of Mad After the death of Mad founder-publisher William Gaines in 1992, publishing company/owner Time Warner positioned Mad under the purview of fellow-publishing-subsidiary DC Comics. After this shift, Orlando became the magazine's Associate Publisher. Concurrently, he was involved in creating exclusive Mad products for the then-new Warner Brothers Studio Store on Fifth Avenue. Although he retired from DC in 1996, he nevertheless maintained an office at Mad where he worked on Mad cover concepts and other projects for the next two years. He illustrated four additional articles for publication in Mad with the last appearing in the July 1997 issue. At the time of his death in 1998, he was survived by his wife, Karin, and four children. Reprints Orlando's artwork for EC Comics has been reprinted extensively by publisher Russ Cochran. Following the 2006 culmination of Cochran's Complete EC Library reprint series with the EC Picto-Fiction volumes, other EC reprint volumes featuring Orlando illustrations have been published by Steve