Sorry for the wall of text, but I recommend all of these movies.
Office Space
This is one of the most well put together movies i've ever seen. Its a comedy based on some of the most stereotypical office personalities you can imagine. I highly recommend it.
Anchorman
This is a very dumb but enjoyable comedy making fun of news teams. Its Will Ferrel's best movie in my opinion, but you wont want to watch it if you aren't into cheesy.
What About Bob
This is a great movie about a guy that drives a psychiatrist insane. There's not too much else to say about it, but trust that it's extremely funny and awesome.
Miyazaki Movies
There's Howl's Moving Castle, Laputa: Castle in the Sky, Princess Mononoke, Or Spirited Away. Take your pick. They're all good if but a bit weird. (They're Anime styled if that's a problem.)
The Island
A pretty sick and awesome story about clones who are used to replace the dieing organs of rich people. Its a great story, and the setting is done extremely well (Futuristic). (It's the only Micheal Bay movie I like besides transformers, and thats only when I want to watch explosions.)
Se7en
A physchological thriller about a serial killer approaching his deaths by the seven sins, with Brad Pitt and Morgan Freeman working against him. A great movie.
October Sky
An extremely good and well paced movie about a group of boys from a West Virginian coal town that have ambitions to base their futures on scholarly means as opposed to dieing whilst working in the mine-shafts. I highly recommend it.
Apollo 13
A great Tom Hanks movie about "Apollo 13". I'm sure you know the story, but its still a great movie.
Crank & Crank 2: High Voltage
These are great movies because they're so graphic and action-intensive. Dont watch them if you're expecting a story, otherwise they're awesome.
Funny Farm
A kickass movie about a guy that buys a house out in the country who quickly begins to hate it. Its a comedy that investigates a few country based stereotypes. Highly recommended.
Batman Begins
Its the first batman movie that you can take seriously. Screw Tim Burton's old ones.
The Dark Knight
Its the second batman movie that is also quite awesome. (You should watch both of them.)
XxX
"Triple X" is not porn, as the name might mislead. Its an action movie that is clearly exaggerated, but also thoroughly enjoyable. Its scened in some neat European places.
Fight Club
This is a kickass movie over a guy that turns from his safe workaholic lifestyle into a anarchy fueled terrorist. Its much deeper than that, but its a great movie that gets better every time I watch it.
American History X
Another very good movie exploring the lifestyles and regrets of skinheads. Its pretty good.
Almost All Pixar Movies
The Incredibles, Toy Story, Cars, Finding Nemo, Ratatouille, Up, and Wall-E. They're all really awesome animated movies.
Forrest Gump
Another Tom Hanks movie about a 'slow' guy that does more in his life than any of us probably ever will. A great movie.
Cast Away
Yet another Tom Hanks movie about a guy that gets stranded on an island. Its a good survival movie.
Harry Potter Movies
Not everyone might like them, but they're pretty good movies. I almost look to them for their art department more than the actors themselves.
A Beautiful Mind
A great movie about a crazy mathematician. Its an extremely great movie.
Monty Python and the Holy Grail
If you've not heard of this movie, damn. Its great brit-humor.
Pans Labyrinth
A movie about a girl living in a troubled time juggling reality and a fairy tale. Its a great movie, but dont watch it if subtitles disturb you.
Hellboy 1 & 2
Hellboy 1 sucked, but the second one is good enough to warrant the continuity I think. Two is actually a great movie full of action and humor. The first one is a bit weird.
Back to the Future
All of these movies are fun exploring the possibility of time travel. Highly recommended.
Next
A Nicholas Cage movie about a guy that can see himself two minutes into the future. A highly enjoyable movie.
[b]The Rock[/b]
Another Nicholas Cage movie about Alcatraz island being captured by terrorists and re-claimed. An enjoyable action movie.
Star Trek
I thoroughly liked all of them because I love star-trek. If you're not a fan of Shatner or Patrick Stewart, then just watch the new one. Some are more watchable than others.
The Last King of Scotland
A great and scary (in the sense that it would suck to be the main guy) movie about a doctor that leaves to help people in Africa before becoming the personal doctor of a cruel two faced leader there. A really good movie.
Gladiator
A kick ass movie about a prominent general that gets captured and thrown into being a gladiator. A great movie with nice settings.
300
A shallow but very awesome action movie where an army of 300 arrogant people kick the armies of King Xerxes asses.
Die Hard With A Vengeance
A really fun to watch action movie of Jeremy Irons as a mad bomber who uses his bombs to manipulate the police into doing his bidding. Highly recommended.
Donnie Darko
A bit of a weird movie of a twisted kid. I dunno, I wont say much. It is a little depressing though I suppose.
Scarface
A classic old movie where Al Pacino climbs the ladder of the drug cartels. A really good movie.
The Devil's Advocate
An extremely good movie about a lawyer who begins to work for a law firm in New York before running into a variety of satanic problems. Its another Al Pacino movie that I cant recommend enough. Its a great movie.
Groundhog Day
This is a thoughtful, hilarious, and deep movie about a weather man who relives the same day over and over. This movie I cant recommend enough either. Bill Murray puts on a great performance.
V for Vendetta
A great government satire. That's really all there is to say.
Children of Men
This movie is about a society of people that have lost the ability to have children, until one comes along. This movie has an extremely prominent Half-Life 2 vibe to it. If you see it, you should know what I mean. Its a good movie too.
Glory
A movie about the first black regiment of the union in the US civil war. Its a great movie.
Men of Honor
This is a really great movie about a black guy (in an oppressed time) that becomes a navy diver. It has great performances from Robert De Niro and Cuba Gooding Jr.
The Shawshank Redemption
This is another of those extremely highly recommended movies about a guy that gets wrongfully arrested and makes his way through prison life. You really should watch this movie. The ending is satisfying.
Enemy of the State
This is a Will Smith movie where a run-in with a guy wrongfully sets the pressure and tools of the government in trying to cover a scandal. Its a really great movie that you should watch.
American Gangster
This is a movie in which a guy builds an empire of 'gangsters' that surpasses the traditional mafias in Manhattan.
Independence Day
A great action movie where the stereotypical United States becomes the only hope for the world to repel a dominating alien race. Dont get me wrong though. I enjoyed it quite a lot, and the sountrack and art direction is great. The
I. Robot
A detective sort of movie based in a future where fully autonomous robots begin to revolt against mankind. Its another great movie with good art direction and a good story.
I Am Legend
This movie gives me another HL2 vibe. The story isn't too particularly awesome, but its a good zombie sort of survival movie. The ending will probably piss you off though.
AI: Artificial Intelligence
This is another robot movie (Steven Spielberg) that follows the creation and life of a robot boy. Its great movie balancing action, story, and great art direction. (The ending is very disappointing though.)
Dawn of the Dead
If you love L4D, you will love this movie. It explores several aspects of surviving a zombie attack in a highly enjoyable way. A great great movie.
The Last Samurai
This is a long Tom Cruise movie where he brings western guns and other weapons to Asia, before being captured and slowly adopted into a samurai lifestyle. Its a pretty good movie, except for the end where all the honor bullshit gets them all killed. Its a great movie with some great scenery and fight scenes.
Toy Soldiers
This is a movie about a school that gets seized by terrorist, with a group of mischievous boys trying to repel them. Its a pretty good movie, and you get to see "Sam" from the Lord of The Rings in a different setting, which is refreshing.
The Life Aquatic with Steve Zissou
This is another Bill Murray movie that's a bit weird to watch. Its pretty funny, and it has a weird but enjoyable soundtrack. You'll notice more every time you watch it, if you do that is.
Definitely, Maybe
Its one of those love story movies, only its actually good! Its got a lot of charm to it, and its actually very funny. I really liked it, at least.
The Legend of the Drunken Master
This is a great Jackie Chan movie ("Foreign", it wasn't filmed in English). Its funny and serious at the same time, with several action scenes that are great. I highly recommend it.
Titan AE
This was an animated film (doesn't fit an Anime style, although its cartoon) about a guy that searches for the way to save the human race (Earth was blown up). Its a pretty good movie, and has some high-profile actors voicing the characters.
Steam Boy
This is another animated film that involves a few people (who are great with steam and machinery) to stop a business from dealing technologically advanced weapons (for them) to various nations of the world. I liked it a lot, and some of the settings are pretty cool to look at.
Men in Black 1 & 2
These two movies are funny and action packed, although they have serious and deep aspects of them as well. I thoroughly enjoyed them both (First one more though)