Whenever I remember that movie this automatically springs to mind.
As far as the musical crowd is concerned I'd say Grease (not 2, DO NOT WATCH GREASE2!!1!) and the Rocky Horror picture show.
Grease 2 is pretty bad, but it rounds the corner from "argh, do not watch" back to "this is pretty enjoyable, why am I still watching this?"
Rock Horror Picture Show is pretty trippy and I still think it is the best for it's camp value alone.
My list: (contains many foreign films and a lot of indie weirdness)
Indie: Amelie - I don't know how to classify this, but maybe as a romantic comedy film? It's a not one by Western standards of comedy, but it's kind of fun. The character is Amelie Poulin and she tries her best at making people happy in their daily lives, and she eventually meets the "love of her life". It's pretty fun, and it's subject matter can get pretty dark in tone...dealing with death, loss and sexual matters. This movie will definately make you cry and laugh. (Also, it's a pretty fun date movie, if you and your date know each other pretty well.) Only thing is...subtitles if you don't speak a word of French.
Amelie Trailer:
Musical: Rent - I know, most people would dismiss this as glorifying "pseudo-hipsters". It's a pretty original broadway production and the characters are pretty interesting. Plus there is a love story for everyone, from the gay guys to the lesbians to the straight couple...and the music gets completely stuck in your head! I'd probably describe this as a story about a bunch of friends/lovers weathering good times and bad times in New York City. It's pretty fun and be prepared to shed a few tears at some points. (Also, I might be killed for suggesting this - the film version has better pacing and character development.) It's also about fighting the stigma of AIDS/HIV and it's a pretty powerful piece. There's only one dull moment in this - the scene with the spoken word performance...but if you like this kind of thing, you'd go for it.
Rent Movie Trailer:
Musical 2: Cabaret - Okay, okay, this is an extra musical, but it's still pretty well done. Set in a Cabaret at the beginning of World War 2. It can get pretty dark and pretty weird before it gets done. There was a broadway version with Alan Cummings in it as the MC. Pretty interesting. I would say it's more of a character driven piece in which characters are described with their own musical score. I love two songs in this - Two Ladies and Liza with a Z. It's racy, it's raunchy and it's fun - and you can see the characters desperately escaping their own mundane lives in the Cabaret.
Cabaret Trailer:
Big Budget: Star Wars (original trilogy) - Good and evil and the original father-son relationship drama, set to semi-religious connotations and in the future. Also because it showcases the talent and people who were behind the idea and the execution of the ideas! Features a few new ideas - like the lightsabers and very technically good....also good for the pop culture references. (Believe it or not, one o
f my nerdy/geeky friends hasn't seen this!)
Foreign: Drunken Master - Featuring a real fighting style and a really young Jackie Chan. The choreography is highly excellent and makes for a tense battle scene. Also, one of the first use of the Hong Kong style of "wire fu", a style that uses wires and grapples to pull actors and punches. Also, one of the better funny foreign movies. (The end fight is one of the best in movie history.) Some of the humor is pretty low brow, although - with Jackie's character refusing to practice the stances of the female "drunken god". (Also, one of the few martial arts movies that sounds like a fighting video game.)
Drunken Master 2/Legend of Drunken Master Trailer:
* Note: Trailer is from the more recent Drunken Master 2. The fighting style is similar, but not the same.
Classic: Citizen Kane - Yes, this film that is an essay question by every single university student. It's a great example of an introspective film. *It's the film equilivant of "The Great Gatsby" - just basically how a wealthy man gains power and prestige by working hard and finally realizing that he lost his soul or his personality in the pursuit of money and fame. It's pretty good, although the film's pacing is slow (probably on purpose), and the character development is plodding as well. Watch it with a great big tub of popcorn and you'd be able to have fun. (I had to watch this for the first time in first year university and I only sat through it with the help of snacks - 5 hour classes are so not good!)
Introducing the Characters in Citizen Kane:
Extra Credit: Bridget Jone's Diary - This is the ultimate example of a "chick flick". This is based on a book that spawned out of a relationship advice column in a UK newspaper. It's biggest achievement is completely capturing the spirit of every insecure moment of a woman's life...and what her thoughts were on the subject. I actually love this movie, despite the cheesy nature of that. (Also, I'm told that Hugh Grant and Colin Firth are completely attractive to those who like men.)
Guys, watch this and you'd no longer wonder why women are pretty damn insecure! (Also...the lady who plays Moaning Myrtle in Harry Potter is one of Bridget's friends.)
I'm actually ashamed to really like this, being a card carrying feminist as well. The character is pretty bad...kind of a ditz, airhead and completely weird. I would say this movie is Pretty Women rewritten from the female perspective and with a healthy heap of funny.
Bridget Jone's Diary Trailer:
