@Scepticalscribe, not sure whether you were asking me to add my reasons for choosing the movies I did...
Anyhow, I've used my own, highly subjective parameters that are all over the place, so some are in my list because I have emotional ties to them, others are cinematographically brilliant, among other things.
The Last Wave is on the list because it excels in everything. The screenplay was pretty much non-existent. Some of the actors (Aborigines) weren't even professional actors but the only "true" tribal people left in Australia. The story itself is captivating and highly engaging. The end can be interpreted in many ways and there is no definite answer. This is one of those movies that you can't watch just once and something new to ponder about pops up with every viewing. Most people would likely find it boring. I find it fascinating to no end. An overall brilliant, smart, low-key, zero(!)-budget movie with excellent actors. The cinematographic aspect doesn't fall short either. The imagery is so timeless, it could have been shot today. Or a hundred years ago. Anyone who loves to chew their nails in despair while figuring out the great questions of life - as well as the smaller ones - will find this movie a good fit. As a side note; This is probably one of Richard Chamberlain's best acting. This movie is supreme beyond words and a true labor of love by everyone involved.
Cleopatra is a two-fold thing. It's nostalgia as I watched it the first time when I was around 8. Now, a good three decades later, I still am in awe. This movie has triggered my interest in history - particularly Roman and Egyptian history - at a very young age and has formed and highly influenced many of my educational decisions later in life. It's also simply a great movie, even without a backstory. The cinematography was unbeaten and highly progressive for its time. The actors are great, the story, while not 100% accurate - as is the case with pretty much all of the more known Hollywood movies that deal with ancient (or contemporary) history - is solid, the actors are great, though I'd highlight Roddy McDowall who plays the role of Octavian (Augustus). I've not seen all of his works but he easily surpasses Richard Burton (that says something) with a tour-de-force acting performance. It's definitely left a mark.
North by Northwest is also mainly a childhood pick. That and the fact that I love almost all of the movies in which Alfred Hitchcock had a hand. Powerful scenery, wonderful soundtrack, just overall a great classic with nice twists that weren't obvious to me at the age of 8. I've seen it a dozen times (like all of the movies in this list) and it's still a great way to waste nearly 2.5 hours.
The Kid is representative of my love for Charlie Chaplin's works. All of them. And it features the magical Jackie Coogan! I've never seen a child perform like this. It's made me shed many tears. It's a fine silent movie, nothing out of the ordinary in terms of story, but the execution and timing are perfect, as are all of Chaplin's movies and shorts.
Once Upon a Time in America is representative of my fascination with Mafia/gangster movies of that era. I like The Godfather trilogy almost as much, or Goodfellas. But I think Time in America stands out and prefer it over the rest. I don't actually know why. I just think the mixture of life/love/tragedy are best balanced in this movie. And the soundtrack kills me.
Ordinary People is another childhood mention. I was around 8, so this is another thirty-year-old memory. The story is tight and gripping, highly emotional and probably one of the first movies that highlighted the field of psycho-therapy without exaggeration or "over-the-top" nonsense. All three of the main actors, Donald Sutherland, Timothy Hutton, and Mary Tyler-Moore truly nail their roles, Moore is probably the most convincing one because you almost begin to deeply despise her while watching. The story itself is very down-to-earth and thus very easy to relate with on a personal level, at least for me.
