The Shawshank Redemption (1994) – Tim Robbins is a good director. He doesn't work for me as a lead actor. He has the right qualities in things like Bull Durham, but like many of his films I think other actors could have done as well or better. The movie was long and Robbins doesn't do much here. But the subtlety works on the second viewing. Morgan Freeman is just excellent in a dynamic performance as a hard man made better through his friendship with Robbins.
Forrest Gump (1994) – The spectacle of the thing is all I could see the first time around. The special effects and Hanks's idiot manchild Rainman performance felt grating to me. A gimmick. But I was surfing around one day and I caught it midway through and it was mesmerizing. Showed it to Abby a few years ago and I think she has watched it 5 times since.
American Beauty (1999) – Annette Benning is too much. The militaristic Great Santini father has been done better. Spacey's and his obsession with a high school girl is creepsville. But once you know the plot and can it's dreamlike quality is captivating.
The Apartment (1960) – I saw this before I experienced the corporate ladder and the corruption of the real world so the subdued humor was lost on me. I have since read the screenplay and the stage directions alone or so funny I laughed aloud. I needed to lose some innocence to appreciate it. It's great and timeless about how limited people can only get ahead through power manipulations.
Heat (1995) – Derivative in the heist genre which it excels at but I didn't appreciate the complexity of career men and their relationships until I saw it again years later.
Vertigo (1958) – One of 5 Hitchcock films owned by the master and barely seen outside of the film buffs for decades until the early 1980s and because I enjoyed Rear Window (1954) in the same batch even moreso I immediately thought Stewart was wrong for the film, something even Hitchcock reflected on. With time I disagree with Hitch and appreciate it on its own. It has detractors. Quinten Tarantino doesn't like it. Even kind of silly to see it lead the Sight and Sound poll in 2012, but still great.
Chinatown (1974) – Another movie I saw when I was too young to appreciate the cynicism when I sought heroes. Nicholson is over his head the entire time and it's true to life rather than the movies I grew up on.
Million Dollar Baby (2004) – Without Eastwood I think this would have been a slight and forgettable story. It brings out everything good about Morgan Freeman and the two of them together made far too films together.
The Third Man (1949) – Saw a public domain copy with a poor soundtrack and didn't appreciate the subtle humor. Saw a restored version later and it was a different film for me.
Network (1976) – Saw the movie when it seemed like an over-the-top dark comedy. It was prescient in a way that Paddy Chayefsky scripts do not get the modern-day credit. You have to be in the right mood for it still, but great at what it was doing.