During one of their stays in Los Angeles, Mœbius introduced Darrow to Frank Miller, which led to a friendship and a number of comics collaborations. Darrow, Miller and Steve Gerber started developing a Superman series as part of the "Metropolis" proposal, then after the idea fell through, Miller offered Darrow to work on a Daredevil story he was writing that would . Eventually, Miller realized he didn't want to be the person to bring Darrow into the world of Big Two work-for-hire, and the two focused on developing their own story. As Darrow has never worked with a writer before, he often strayed from the script, prompting Miller to make a number of significant changes to the story. Between 1990 and 1992, Dark Horse published the three-issue mini-series titled "Hard Boiled", which earned Miller and Darrow the 1991 Eisner Award in the "Best Writer/Artist Team" category. After "Hard Boiled", Darrow wanted to do a superhero story, specifically, an Iron Man story, although Marvel wasn't interested. Miller and Darrow started developing the concept into their next project, "The Big Guy and Rusty the Boy Robot". This time, they worked in the so-called "Marvel style": Miller wrote a few paragraphs describing the general plot, from which Darrow drew the eighty-page story, which Miller then wrote the dialogue over. Between 1993 and the series' first issue, released in 1995, the characters of Big Guy and Rusty appeared in a number of Darrow-illustrated posters and pin-ups, occasionally crossing over with other creator-owned characters such as Spawn and Ash. In 1994, Dark Horse started a new imprint titled Legend, spear-headed by Frank Miller and John Byrne and encompassing works by various creators including Art Adams, Mike Mignola and Darrow. "The Big Guy and Rusty the Boy Robot" was published in two issues in 1995 and 1996 under the Legend imprint. Between the release of the first and the second issues, the characters also appeared in two issues of Mike Allred's "Madman", which was also published under the Legend imprint at the time. The comic book was later adapted into a 26-episode animated series of the same name, produced by Columbia TriStar Television and Dark Horse Entertainment, airing for two seasons from 1999 to 2001.