Robert Downey Jr. has really become one of the most beloved actors in the Marvel Cinematic Universe. It seems as though he finally found his niche playing Tony Stark. But that's not how it had always been for the Iron Man actor. As many know, Downey had drug-related problems and was arrested multiple times, so despite his talent, Hollywood saw him as a liability and wouldn't cast him for many roles he probably would have been perfect for.
Roles in classic eighties and nineties movies such as Say Anything, Wild Things, and Backdraft would have all featured Downey if perhaps he had gotten his life together sooner, but there is one movie where his potential co-star actually rooted for him to get the part.
Downey almost got cast in Pretty in Pink, the 1986 classic teen romance featuring Molly Ringwald. The original script had the character of Duckie getting the girl at the end of the movie, but that was changed right before Jon Cryer was cast. Ringwald wanted Downey to play the role of Duckie, and in the book You Couldn’t Ignore More if You Tried: The Brat Pack, John Hughes, and Their Impact on a Generation, Ringwald said she understood that since the script was changed, it made sense Cryer would play the part.
Ringwald said, “I mean, if they remade the movie now, [Duckie] would be, like, the gay friend who comes out at the end. … I feel bad saying that I really fought for Robert Downey, Jr., because it sort of seems like I don’t appreciate Jon’s performance, which I totally do—it’s just, it really did affect the movie.”
Cryer responded to Ringwald’s comments in the DVD commentary on Pretty in Pink: Everything’s Duckie Edition, saying that, "Molly dropped the bomb that she would’ve been fine with the original ending if Robert Downey Jr., had played Duckie … But since it was me, she just couldn’t see it. It was like, wow, so I’m that unattractive? Thanks, Mol!”
Even though we love Robert Downey Jr., Pretty in Pink turned out just fine in the end, despite what Ringwald might think.