When the news first broke that Robert Downey Jr. was being eyed to reprise his role as Tony Stark/Iron Man in Captain America 3, few could have imagined it would be for an adaptation of Mark Millar and Steve McNiven's Civil War.
During a "Marvel Event" held in 2014, Marvel Studios President Kevin Feige announced that the movie would be titled Captain America: Serpent Society. However, he was just trolling us as Chris Evans, Downey, and Chadwick Boseman soon hit the stage alongside to reveal the Russo Brothers would be helming Captain America: Civil War.
What followed was one of Marvel Studios' best movies; an Avengers-level event, it saw Earth's Mightiest Heroes split in two following the introduction of the Sokovia Accords. It wasn't quite on the same scale as the comic book it shared a name with but it did bring Spider-Man into the MCU, making many a dream come true in the process.
Talking to The Hollywood Reporter before reuniting with Downey for Avengers: Doomsday and Avengers: Secret Wars (where the Oscar-winner will portray the villainous Doctor Doom), Joe and Anthony Russo reflected on enlisting the actor as Iron Man for their follow-up to Captain America: The Winter Soldier.
"We pitched Kevin on the idea and Kevin goes, 'All right, I buy it. Now you guys got to go get Downey,'" Anthony recalled. "And I was like, 'What do you mean we got to go get Downey? Aren’t you coming?' And he didn’t."
Joe added, "Downey was sitting on a chaise lounge, splayed out like a king, on the roof of his office in Venice. Ant and I showed up and we’ve been rehearsing this pitch, and you’re literally pitching the biggest movie star in the world to take his giant cash cow character and convert it into a villain."
"In a Captain America movie," Anthony interjected before Joe pointed out, "In a movie that wasn’t even titled after his character. And it was the pitch of our lives. And he said, 'Yes, let’s do it.' He liked the risk, to Robert’s credit, and that choice led the explosive upside to Infinity War and Endgame."
At the time, Downey was believed to be out of contract and managed to score a hugely lucrative deal that included the Avengers movies mentioned by Joe.
Ultimately, he helped turn the third Captain America movie into a $1 billion franchise, though that momentum sadly didn't continue with last month's Captain America: Brave New World. Downey's latest return came after meetings with Disney CEO Bob Iger and Feige, with him only agreeing to return provided it wasn't as Iron Man.
Avengers: Doomsday is set to be released in May 2026, with Avengers: Secret Wars scheduled to arrive in May 2027.