Bruce Timm is finally getting to adapt one of the most iconic (and controversial) Batman stories, The Killing Joke, but this is hardly the first time plans have been made by DC and Warner to turn Alan Moore and Brian Bolland’s best-selling comic into a movie. They’ve tried twice before, and two very different scenarios caused them to hold off.

The information comes from a new Empire interview with Timm and longtime Batman voice actors Kevin Conroy and Mark Hamill. Much of the focus is on how the animated film’s R-Rating will allow the movie to do justice to the original material, but Timm also notes that the darkness of the story—especially its depiction of Barbara Gordon’s paralysis at the hands of the Joker, an event Moore describes as something he regrets to this day—caused production on potential adaptations to halt twice before. The first time, according to Timm, was the financial failings of Zack Snyder’s Watchmen adaptation, leading to concern at an R-Rated animated Superhero movie wouldn’t work:

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This is actually the third time that The Killing Joke came up for production. The first time, it was because we had told the home video department that chances are if we do this story, it’s going to get an R rating. This was years ago, but they said, “We’re okay with that, but we’re going to kind of hedge our bets monetarily.” The idea was because the source material was not really long enough to do a full movie, we were going to do a shorter movie at a lower price point, so that would hopefully offset the loss of sales that we would have by the fact that it wouldn’t be an all age title. But right around the time we were ramping up, the Watchmen movie was released and underperformed. Everybody kind of took a step back and said, “Well, maybe the time’s not right for an R-rated superhero movie, so put it on the shelf.”

The second was much more pointed at the story’s most controversial moment. Plans began to formulate again in the run up to 2012—but then James Holmes’ mass shooting at a midnight screening of The Dark Knight Rises in Aurora, Colorado caused Warner to back off once more:

A couple of years later, it came up again and we even had started production with character designs and stuff. But then that horrible shooting at the Dark Knight Rises theater happened and everybody got nervous again about it, because of gun violence, so we put it back on the shelf.

Go forward a couple of more years and it came up again. At this point we kind of looked at the whole thing and felt if we were going to do it, there were certain things about the original story that had always kind of bothered me. I mean the idea of adapting this story always kind of terrified me, because of how relentlessly grim and bleak it is. And what happens to Barbara Gordon in the story is very controversial to this day.

The delays have at least meant one positive thing for this new adaptation. Timm and his team have expanded the story of the original comic, including new prequel material that places a much more prominent emphasis on Barbara Gordon as a hero. In the original storyline, she was little more than a plot device, and her paralysis is still seen as a black mark in DC Comics’ treatment of female characters to this day.

The Killing Joke will be available digitally on July 26, with a physical release landing on August 2.