Robert Downey Jr. may be stepping into the role of Victor von Doom in the upcoming Avengers saga but it is hardly his first villainous turn in MCU.

Despite Marvel offering a broad spectrum of films and stories, very few could be considered as interesting as Captain America: Civil War. The days of gritty battles, road chase sequences, mind-controlled assassins, or being ruthlessly hunted down by the Black Panther are all in the rearview mirror. But once, the Robert Downey Jr. film was the peak of MCU quality content as compared to the recent saga that has hardly produced 2 good movies in the last 5 years.

Marvel’s foray into the realm of fantasy and superhero adventure has never been entirely without its faults. In the late 90s and early 2000s, Blade’s big-screen debut ended in a controversial run while Mahershala Ali’s current reboot looks like a distant dream. However, even the vampire-hunting morally grey anti-hero gets to have his day in the sun.

But as far as the complex grey area of morality is concerned, Victor von Doom is perhaps the ultimate dream role one could ask for.

Robert Downey Jr. Gets a Crash Course in Villainy

Contrary to popular belief, Dr. Victor von Doom is not Robert Downey Jr.’s first rodeo playing the bad guy in a Marvel movie. The announcement which came as a shock to some and a surprise to others did not do much good for the franchise in the long run, considering how fans will be putting the former Iron Man star under the microscope as soon as he steps into his role as the villain.

However, Captain America: Civil War once came very close to playing out a similar angle 8 years ago. The Avengers vs. Avengers film was a crash course in how the MCU would fare if its heroes were faced with a morally grey predicament that couldn’t be solved by blasting their way through. In such a scenario, heroes and villains are no longer binary terms categorizable under black & white or good vs. evil.

Instead, emotions, humanity, love, fear, and guilt all churn into an obsidian mix that makes even the best heroes question their roles and turn their back on friends. Robert Downey Jr. walked down that path as Tony Stark and lived to tell the tale. Civil War may have pitted friends against friends and played with an entire fandom’s emotions but it also showed the true nature of humanity and how far one is willing to go for the sake of retribution and revenge.

Russo Brothers’ Plan on Turning to the Dark Side

During the making of Captain America: Civil War, the Russo brothers gave Robert Downey Jr. an offer he couldn’t refuse. They allowed the Iron Man star to unfurl fully by dipping his toe in the pool of villainy after nearly a decade of playing a superhero. While the offer was a tempting one, the sales pitch was even more flattering.

However, there remained a slight wedge in the plan. Robert Downey Jr. was under no obligation in his Marvel contract to do Civil War and by the time of the film’s production, he was already a heavily in-demand A-list star. In a podcast interview with Variety‘s The Big Ticket, Joe Russo revealed how he convinced the actor to forego his contractual rules and come on board the film:

You say, ‘Look, we’re going to try and do something really risky here. We want to deconstruct, we want to inject some edge and some tension into these stories.’ And he has to keep telling these stories, so he wants to play something compelling.

So when you say to him, ‘Hey, you get to be a villain and it’s going to make your next few movies a lot more interesting and give you more to play,’ it’s not that hard to sell.

While Captain America: Civil War may not have been the full turn into the dark side of evil for Robert Downey Jr., one could certainly give the Russos credit for their idea. After all, his role in Christopher Nolan’s Oppenheimer playing the villain did earn him the first Oscar of his career.

Now, Downey Jr. takes it a step further by playing the most sinister villain to ever exist in the Marvel universe, a world he once helped build from the ground up not too long ago as its honorary godfather.

Captain America: Civil War is streaming on Disney+.