So I've asked this question to hundreds of people over the past decade. I wish that I had written down their answers, because it's a great way to learn about others while making a must-have collection list. Please email your personal top five and I will post on this page in the comments section below. Here's how it goes:
If you were on a desert island for the rest of your life, and you could have only five movies to watch over and over again, what would they be? This question is not what are the top five movies of all-time. I think Schindler’s List has to be one of the most-moving and well-made movies, but I would need some serious anti-depressants to continually watch it. To qualify, these movies need to have that 'repeat-ability' element. Also, you probably want some diversity to keep you sane on this island. Sometimes you might be in the mood for adventure or sci-fi, but other nights you might like a romantic comedy.
I'm going to get us started by listing five movies that make a solid list and that I've heard lots of people mention. This is not my personal list as I am not a personal fan of number five, but it's makes the list by popular request.
1. The Princess Bride: This one continually comes to the top, and if you ever watched USA in the late 1980s and 1990s, you realize that this movie has been played thousands of time already. I think the appeal of The Princess Bride is that it combines comedy, fairy-tale and love-story all in one. For those avid fans, here's my favorite line when Westley is lying dead (or at least mostly dead) on the table of the local miracle worker:
Miracle Max: Hey! Hello in there! Hey! What's so important? What you got here that's worth living for?
Westley: T-R-U-E L-O-V-E <pressing on Westley chest to exhale air>
Inigo: "True Love", you heard him? You could not ask for a more noble cause than that.
Miracle Max: Yeah, True Love is the greatest thing in the world, except for a nice MLT---mutton, lettuce and tomato sandwich, when the mutton is nice and lean, and the tomato is ripe. <makes puckering sound> They're so perky. I love that. But that's not what he said---he distinctly said "To blave" and as we all know, to blave means to bluff, heh? So you were probably playing cards, and he cheated (you can find the whole script at http://fringe.davesource.com/Fringe/Entertainment/Scripts/The_Princess_Bride.html)
2. Love Actually: If you're on a desert island, you're probably going to want to feel good at the end of the movie, and Love Actually nails it. If you haven't seen, it's an emotional roller-coaster of people's lives around Christmas filled with infidelity, political posturing, boyish love, immense loss and true friendship. When the guy stands at the front door with the carol music playing and flipping the cue cards, it gets me and Sam every time.
3. Star Wars (The Original, A New Hope, 1977): This is one of the best films ever made. For anyone who dismisses it as science fiction, I'd like to say, look at the scoreboard. It held the best-selling movie title for over 20 years until Titanic came along (http://articles.latimes.com/1998/mar/16/local/me-29454). It's the classic hero story that follows the format told since ancient times. I wrote my admissions essay to Harvard on it. You may laugh, but here it is Harvard Admissions Essay (Star Wars).
4. Monty Python's and the Holy Grail: People either get the humor of Monty Python or they don't. The references to this movie are countless. What is the air-speed velocity of unladen swallow? You got to love when King Arthur tries to ingratiate God. Arthur: "Good idea, my lord" God: "OF COURSE IT'S A GOOD IDEA"
5. High Fidelity: Honesty, I didn't think this movie was that great, but for some reason, it is one of the most popular responses, so I felt compelled to post. If you're interested in why people like, you can try this link (http://www.filmschoolrejects.com/features/movies-we-love-high-fidelity.php). If I were to substitute, I think I would add when Harry Met Sally, Good Will Hunting, or a personal favorite, the Thomas Crown Affair, which no one else seems to like.
As for the trip, I'm still having a blast. I got to watch Phil Ivey make the final table of nine, which will be played in December. In addition I've played well in tournaments but have lost my shirt in cash games for poker. That said, I don't mind saying that I played my cards and lost. It is part and parcel of figuring out what you're good at (If by Rudyard Kipling). I'm meeting up with Cheryl today to head down to Fremont St, which should be fun. Send me your desert island movie list and keep posting comments (I'm happy to see someone's reading at least).