In 2004, Frank Miller received a seven-figure upfront payment to bring “Sin City” to the big screen from Dimension Films, as well as a share of profits from the film. He wrote the screenplay and co-directed the movie, which took in more than $160 million in worldwide box office and was a DVD hit. Then he signed to do two more installments of the series for Dimension. He’s conservatively estimated to have made more than $10 million for the package.

The anti-heroes at the center of today’s graphics novels like “Hellboy” and “Sin City” are far more complex and nuanced than classic characters like Superman and Batman. The same could be said of deals for the rights signed by their creators. And the deals are far more lucrative for the creators, as well.

The deal cut by Miller, a comic book icon, was an exception. But savvy modern comics writers, enlightened in part by the financial struggles of their predecessors, have cut broad and creative rights deals covering not only film and TV, but video games and DVDs, as well as emerging platforms like wireless and broadband.

In addition, they’re going through independent publishers, rather than working with the majors.

Siegel and Shuster, who worked in the Great Depression, never thought about television rights, much less iPod broadcasts.

“When Siegel and Shuster created Superman, they didn’t think it was going to become an icon and part of the nation’s mythology,” said comic book creator Marc Andreyko, 35. “It’s like saying John Wayne didn’t know his movies would be out on DVDs. The opportunities created by technology and how small the world has become and the output for entertainment are so much more vast than they were 60 years ago, even 20 years ago.”

While the creators never cashed in, the Man of Steel nonetheless changed the contract landscape for comics creators.

“It really wasn’t until the first ‘Superman’ movie (in 1978) that people started looking at comic books in a whole other way,” said Steven M. Weinberg, a partner at Greenberg Traurig LLP, who has represented Marvel Comics founder Stan Lee. “‘Superman’ was a blockbuster (the three films grossed more than $300 million for Warner Bros.). I don’t think that had been seen before.”

Hollywood achieved more comic-based film successes, including Superman’s DC Comics stable mate, Batman. Warner Bros., like DC under the Time Warner Inc. corporate umbrella, reaped $700 million on three films based on the Caped Crusader. However, it was the incredible box office grosses realized by Sony, when it produced two films featuring Marvel’s Spider-Man, which kicked the comics-to-film biz into high gear. The first “Spider-Man” recorded the biggest box office opening in history, with $114 million in three days in 2002. Overall, Sony reaped more than $1.6 billion on that film and its sequel, and millions more in ancillary receipts.

Platforms proliferate
Along with the box office numbers – comics-based films have brought in $14 billion since 1978 – the proliferation of media platforms has also upped the ante for comic book creators.

“I think what’s really happened over the last 20 years is, especially with the explosion of cable TV and the Internet, that animation has risen to new heights as has the popularity of various characters,” Weinberg said.

All of which provides potential for revenue streams, for the owner of the characters.