5. Youd be working for me, mostly undercover Redford teaches Pitt the Ropes Spy Game (2001)
Without wishing to sound like a broken record, Spy Game is possibly Scotts most underrated movie. Made in 2001, at no point does the film feel old fashioned, yet at the same time the film somehow manages to feel very traditional, almost like a celebration of great spy movies gone by. The movie largely takes place in an office at a CIA building with Robert Redfords Nathan Muir telling his side of events which are shown in flashback. Being a spy thriller there are twists and turns but essentially Muir is trying to protect his friend, the spy-gone-rogue, Tom Bishop, played by Brad Pitt. The way the movie is constructed, right down to the very end, is like a less cool version of The Usual Suspects, but Scotts not trying to be cool. It might seem an odd choice to pick a montage as the greatest scene, we all know how montages work and what theyre there to do, the South Park guys even wrote a song about it, but theres so much to enjoy about this one. Redford is a magnetic screen presence and Tony Scott cant take credit for that, but the casting of Redford alongside Brad Pitt was like Redford passing the baton to Pitt who has more than earned it. The montage works because despite being the two leads, Redford and Pitt dont really share a lot of screen time, so for the 3 or so minutes in which this montage takes place the audience can sit back and enjoy 2 classy A-listers do their thing. Whats more is that Scott has fun with it. Pitts character is effectively an updated version of Redfords character from Three Days of the Condor, so who better to teach him his craft than the man himself, something that wouldnt have passed Tony Scott by. In addition, in one sequence involving Pitt learning how to question for information their resemblance to Woodward and Bernstein, aka Robert Redford and Dustin Hoffman in All the Presidents Men is uncanny. Scotts direction, for him at least, is relatively unfussy, he stays out of the way and lets the actors do their thing and you get the sense he enjoyed watching this back as much as the audience did.