Movie Answers
Here are the answers. I waited for more guesses...and none came, and I grew restless. So there you go.
1. "I can't believe what a bunch of nerds we are. We're looking up 'money laundering' in the dictionary." Office Space - Guessed by
thecomfychair
2. "I thought all writers drank to excess and beat their wives. You know one time I secretly wanted to be a writer." The Philadelphia Story
3. "I'm pretty sure there's a lot more to life than being really, really good looking. And I plan on finding out what that is." Zoolander - Guessed bythecomfychair and 
mystic_amor
4. "Please! This is supposed to be a happy occasion. Let's not bicker and argue over who killed who." Monty Python and the Holy Grail - Guessed bythecomfychair
5. "In punishment for lack of an interesting pirate name, Peter shall walk the plank." Finding Neverland - Guessed bythecomfychair
6. "Well, I've wrestled with reality for 35 years, Doctor, and I'm happy to state I finally won out over it." Harvey
7. "We're all put to the test... but it never comes in the form or at the point we would prefer, does it?" The Edge
8. "Classes will dull your mind, destroy the potential for authentic creativity." A Beautiful Mind
9. "A fencer is always in danger of revealing his intentions to his adversary - and that he must never do." The Swan
10. "Please don't call me by my real name, it destroys the reality I'm trying to create." The Man Who Knew Too Little
11. "Why would anyone want to get over the one thing you hope for from the minute you're born and remember until the day you die?" Guys and Dolls
12. "I killed two people. One was... yesterday? He was just a boy and I led him into quicksand. The other was... well, before Aqaba. I had to execute him with my pistol, and there was something about it that I didn't like...I enjoyed it." Lawrence of Arabia
13. "Death of a loved one can lead people to do the strangest things." The Others
14. "When my son was born healthy, I never asked why. Why was I so lucky? What did I do to deserve this perfect child, this perfect life? But when he got sick, you can bet I asked why! I demanded to know why! Why was this happening?" Awakenings
15. "Sometimes we don't do things we want to do so that others will not know we want to do them." The Village - Guessed bythecomfychair
16. "I knew a man once who said, 'Death smiles at us all. All a man can do is smile back.'" Gladiator
17. "American millionaires must be all quite mad. Perhaps it's something they put in the ink when they print the money." How to Steal a Million
18. "Oh, it's all right, Joe. It's all right. It's my dog. And, uh, my wife." The Thin Man
19. "Hey, you wanna hear my philosophy of life? Do it to him before he does it to you." On the Waterfront - Guessed bymystic_amor
20. "Yes, what's to become of the wretched creatures? Perhaps we should have drowned some of them at birth." Pride and Prejudice (1940)
Good job everyone. :)
1. "I can't believe what a bunch of nerds we are. We're looking up 'money laundering' in the dictionary." Office Space - Guessed by
thecomfychair2. "I thought all writers drank to excess and beat their wives. You know one time I secretly wanted to be a writer." The Philadelphia Story
3. "I'm pretty sure there's a lot more to life than being really, really good looking. And I plan on finding out what that is." Zoolander - Guessed by
thecomfychair and mystic_amor4. "Please! This is supposed to be a happy occasion. Let's not bicker and argue over who killed who." Monty Python and the Holy Grail - Guessed by
thecomfychair5. "In punishment for lack of an interesting pirate name, Peter shall walk the plank." Finding Neverland - Guessed by
thecomfychair6. "Well, I've wrestled with reality for 35 years, Doctor, and I'm happy to state I finally won out over it." Harvey
7. "We're all put to the test... but it never comes in the form or at the point we would prefer, does it?" The Edge
8. "Classes will dull your mind, destroy the potential for authentic creativity." A Beautiful Mind
9. "A fencer is always in danger of revealing his intentions to his adversary - and that he must never do." The Swan
10. "Please don't call me by my real name, it destroys the reality I'm trying to create." The Man Who Knew Too Little
11. "Why would anyone want to get over the one thing you hope for from the minute you're born and remember until the day you die?" Guys and Dolls
12. "I killed two people. One was... yesterday? He was just a boy and I led him into quicksand. The other was... well, before Aqaba. I had to execute him with my pistol, and there was something about it that I didn't like...I enjoyed it." Lawrence of Arabia
13. "Death of a loved one can lead people to do the strangest things." The Others
14. "When my son was born healthy, I never asked why. Why was I so lucky? What did I do to deserve this perfect child, this perfect life? But when he got sick, you can bet I asked why! I demanded to know why! Why was this happening?" Awakenings
15. "Sometimes we don't do things we want to do so that others will not know we want to do them." The Village - Guessed by
thecomfychair16. "I knew a man once who said, 'Death smiles at us all. All a man can do is smile back.'" Gladiator
17. "American millionaires must be all quite mad. Perhaps it's something they put in the ink when they print the money." How to Steal a Million
18. "Oh, it's all right, Joe. It's all right. It's my dog. And, uh, my wife." The Thin Man
19. "Hey, you wanna hear my philosophy of life? Do it to him before he does it to you." On the Waterfront - Guessed by
mystic_amor20. "Yes, what's to become of the wretched creatures? Perhaps we should have drowned some of them at birth." Pride and Prejudice (1940)
Good job everyone. :)