Stradley's work on issue 86 of Marvel's Star Wars series in 1984 was his very first work in the comics industry. He later went to become VP and business partner with Mike Richardson, who founded Dark Horse comics in the 1980s to focus on movie-licensed comics. The company acquired the license for Star Wars comics in the early 1990s, a few years after the end of the Marvel run and in the build-up to the prequels, relaunching the Star Wars line with such titles as Classic Star Wars (reprinting the original Star Wars newspaper strips), Star Wars: Dark Empire, Tales of the Jedi, and Star Wars: Dark Empire II. Stradley and Richardson teamed up to write the Star Wars: Crimson Empire miniseries, focusing on the Emperor's Royal Guard.
Editing of Dark Horse's Star Wars line passed through a number of hands before Stradley assumed the role of Star Wars Senior Editor in 2002, as Dark Horse reorganized its Star Wars line after the release of Star Wars: Episode II Attack of the Clones. He held the position until Dark Horse lost its Star Wars license in 2014.
Randy Stradley was the first to think up the idea of Chewbacca dying in the New Jedi Order series.