2. Spy Game (2001)
In some ways you can consider it a tribute to the late Tony Scott that two of his films made the list; nonetheless, this film would have made this list no matter who the director was, and it is also probably the most underrated of the list. In Robert Redford's last great role to date, he plays Nathan Muir a senior CIA spook on the last day on the job. Brad Pitt is his surrogate son, Tom Bishop, who botches rescuing an inmate from a Chinese prison and is immediately convicted to die in the morning. Muir has to negotiate with his superiors to organize rescue, but there is a problem: they have no desire or need to do so, and Bishop is on his own. So he now has to stall by narrating his time working with Bishop in order to devise a prison break plan, from the other side of the world. All in a days work for him... The real core is Robert Redford as Muir and his interactions with both Bishop and the committee. As he confuses and confounds those higher up the ladder of power than him into giving him more information about the situation in China, we see through his story the complex relationship the two spies formed over two decades. From trainee to full-fledged partner-in-crime, Bishop is the archetypal naive wide-eyed recruit, who never losses his idealism. The whole thing plays out as a life or death high stakes power game, all depending on the mentor to do all that is necessary to save the student.