The 38-year-old actor told The Hollywood Reporter he had "never had a better audition in my life", so was naturally devastated when he was pipped to the role of district attorney William 'Willy' Beachum.
"I hate auditioning. I despise it. I think most actors do, but I got that one and knocked it right out. And it was so great and I had such a great rapport with the director and really felt like it was coming my way."
Chris added: "Anthony Hopkins was already attached and you really think, this is another one of those moments where I might be able to turn a corner. And to lose that one... obviously, Ryan, if you're going to lose to someone, lose to Ryan. But it was just one of those things where you think, 'Man, this is tough'."
Other movies that Chris missed out on around that same time were "Gone Baby Gone", "Milk", and "Elizabethtown", and the actor recently admitted the disappointments, along with on-set panic attacks, almost led him to quit acting.
"There was a period of time where you start thinking, 'Man, I can't make a good movie. I don't know what it is. I wonder how many chances I'm gonna get at this'," he shared.
Fortunately for Chris, he soon landed the career-making role of Captain America in "The Avengers" franchise and went on to become one of Hollywood's most popular stars.