In 1966, Joe Orlando and writer E. Nelson Bridwell created the parody superhero team The Inferior Five in Showcase #62 (June 1966). This lighthearted feature would soon receive its own ongoing series. Orlando launched the Swing with Scooter series with writers Barbara Friedlander and Jack Miller in July 1966. After 16 years of freelancing, Orlando was hired in 1968 by DC Comics, where he was the editor of a full line of comic books, including Adventure Comics, All-Star Comics, Anthro, Bat Lash, House of Mystery, Plop!, Swamp Thing, and The Witching Hour, also scripting for several of these titles. Orlando coined the names of the Weird War Tales and Weird Western Tales titles. While serving as DC’s vice president, he guided the company’s Special Projects department. This included the creation of art for T-shirts and other licensed products, negotiating with such companies as American Greetings and Topps, working with editor Joey Cavalieri on Looney Tunes Magazine and supervising production of trading cards, Six Flags logos, DC character style guides and other items. In the late 1960s, Joe Orlando hired Filipino artist Tony DeZuniga for work on some of DC’s horror titles. In 1971, Orlando and DC publisher Carmine Infantino traveled to the Philippines on a recruiting trip for more artists. Alfredo Alcala, Mar Amongo, Ernie Chan, Alex Niño, Nestor Redondo, and Gerry Talaoc were some of the Filipino komik artists who would work for DC, particularly in the 1970s 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. Joe 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.