Too Late the Hero (1970): Caine works with director Robert Aldrich who follows up his 1967 anti-war story The Dirty Dozen with this darker, more cynical take on war. Unique and interesting, it isn't an easy movie to re-watch repeatedly, but it leaves an impression like few other movies. Caine co-stars with Cliff Robertson, the two actors working perfectly together. Stick with it through the ending, one of the most adrenaline-pumping, chaotic finales ever.
Harry Brown (2009): Harry Callahan meets Paul Kersey meets forced retirement, Caine playing an old man fed up with the violence and murder seemingly so readily accepted in society. Good enough movie, but it never adds a new wrinkle to the vigilante angle.
Play Dirty (1969): One of the most underrated war movies ever made, basically pushed aside since its release over 40 years ago but now available on DVD. Caine plays Capt. Douglas, an engineer assigned a nearly suicidal mission in North Africa in WWII, his team composed of crooks, murderers and rapists. There aren't too many war movies like this, and I guarantee that ending will shock and surprise you. Completely out of left field...in a good way.
Children of Men (2006): It is sometime down the road, and civilization looks to be facing its own death. No one can have children anymore until Clive Owen discovers a young African girl several months into a pregnancy. Dystopian story that was one of the best movies of the 2000s. Caine delivers as always in a funny part, an aging hippie working against the system.
Inception (2000): Director Christopher Nolan tops even himself in this action thriller based in our dreams. What if we could implant a thought or steal someone else's dreams? Leonardo DiCaprio, Ken Watanabe, Ellen Page, Tom Hardy, Joseph Gordon-Levitt and Caine (basically an extended cameo) star in one of the most original, well thought out movies I've ever seen. A classic.
Victory (1981): Michael Caine, Sylvester Stallone and soccer star Pele play Allied P.O.W.'s in occupied Germany forced to play a soccer game with their German captors. Sounds ridiculous, but this sports story is a ton of fun, from director John Huston and also featuring Max von Sydow.
Flawless (2007): Caine and co-star Demi Moore make for an interesting pair in this unlikely heist film set in 1960s London. Very stylish with a good twist toward the end.
The Wilby Conspiracy (1975): An action movie with a message, a story with South African apartheid as the backdrop. Caine and Sidney Poitier play an Odd Couple of sorts (re-done and re-worked some 30 years later in Blood Diamond) navigating their way across war-torn South Africa.
The Prestige (2006): Another film with Caine working alongside director Christopher Nolan. Pretty reflective of the parts he's taken later in his career. Supporting part, but one that makes the movie better just for being there. Mystery thriller keeps you guessing, also featuring Christian Bale and Hugh Jackman.
The Wrong Box (1966): Funny, dark, off-the-wall British comedy. Caine, John Mills, Peter Sellers, Dudley Moore and Ralph Richardson keep the laughs coming throughout.
Battle of Britain (1969): The British equivalent of the American 'The Longest Day.' Somewhat condensed story of England's courageous defense against seemingly unstoppable German forces. Name a British actor from the 1960s, and there's a good chance they have a part -- however small -- in this WWII story from director