Joseph Orlando was a comic book artist, who was considered a star amongst pirate comic artists.
Joe Orlando transitioned smoothly from science fiction and horror to different atmospheric demands of pirate stories. He drew the Sargasso Sea Stories in EC's Piracy magazine that were well-received.
Editor Julius Schwartz managed to hire him for National Comics where he drew the highly anticipated Tales of the Black Freighter in 1960. Issue #1 was written by newcomer Max Shea. Orlando drew issues #1-#9 (with the exception of the back-up feature Galapagos Jones that lasted until #6). He was famous for his shadows, textures and faces. His masterpieces were some panels from "Between Breaths" and "The Shanty of Edward Teach".
From issue #5, Orlando and Shea shared praise but Shea's ego was so elated receiving fan mail that he saw himself as the driving force and became increasingly resentful of Orlando's work. He harassed him with overly detailed descriptions and endless requests for revisions. Because of the friction, Orlando asked Schwartz to take him off the book and his last collaboration was issue #9. Art was taken over by Walt Feinberg.
- Joe Orlando was a real-life comic book artist who had collaborated with Alan Moore. The above story is a fictionalized version of him in the alternate history of Watchmen.
- The Book of Rorschach, an in-universe album by the fictional band Sons of Pale Horse, credits Joe Orlando's son, Joe Orlando, Jr., for designing the album's artwork.
- In 1987, Joe Orlando created an illustration for a page for "The Shanty of Edward Teach", a story from the comic-within-the-comic series, Tales of the Black Freighter, which was featured in the supplemental text piece from Watchmen #5, Treasure Island Treasury of Comics. 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.