1. Guile, Street Fighter 2
2. Lord Alfred Tennyson, Charge of the Light Brigade
3. Cobb and Mal, Inception
4. Asbel Lhant and the one and only M. Ceasar, Tales of Graces
5. Vizzini, The Princess Bride
6. Dennis Green, NFL Head Coach. His Arizona Cardinals were heavily favored to lose against the Bears, and got out to an early lead. They lost the game at the last second in hilarious fashion, leading to this meltdown. Unsurprisingly Green was fired after this season.
7. Zack, Kimberly, Billy, Trini, and Jason, Mighty Morphin Power Rangers
8. Sam Axe, Burn Notice
9. Blink 182, All the Small Things
10. Calvin, Calvin and Hobbes
11. Lionel Hutz, The Simpsons
12. Astaroth and Yuri Hyuga, Shadow Hearts 2
13. Dante, Devil May Cry 3
14. Marcus Bennett, Bad Boys 2. Hot Fuzz was also accepted as an answer here.
15. Manfred von Karma, Phoenix Wright: Ace Attorney
16. Lews Therin Telemon/Rand Al Thor, The Gathering Storm. I wasn't going to use a Wheel of Time question, but my first pick for 16 was super obscure (Megaman X6 line). I went with a quote I rather liked to replace it.
17. Real American, Hulk Hogan's theme. Thank you to Lance for actually knowing this, you were the only person who sent in guesses (Besides Dune) who knew this one.
18. Edward Cullen and Isabella Swan, Twilight.
19. Happy Gilmore, Happy Gilmore. Don't mess with Bob Barker.
20. Clue. This is said by several characters.
Lance: 10/20
Twil: 5/20
Monkey: 5/20
(Dune, doesn't count): 17/20
Alex: 11.5/20. Gets half a point for guessing WoT on 16, and gets full credit for 9.
Snowfire: 9/20. Gets half a point for guessing WoT on 16, and half a point for ballparking 7.
AAA: 10/20
Elfboy: 10/20
Ciddy: 11/20
Ciato: 8/20
Alex manages to steal the show, whee! Thanks to everyone who sent in guesses.
Edit: Who got which questions.
Street fighter: Cid, Alex, Dune, Monkey, Twilkitri, Lance (6/10)
Charge of the Light Brigade: Cid, AAA, Snowfire, Alex, Dune, Lance (6/10)
Inception: Cid, AAA, Snowfire, Alex, Lance (5/10)
Tales of Graces: Dune (1/10)
Princess Bride: Ciato, Cid, Elfboy, AAA, Snowfire, Alex, Dune, Monkey, Twilkitri, Lance (10/10)
Dennis Green: Ciato, Elfboy, Dune (3/10)
Mighty Morphin Power Rangers: Ciato, Elfboy, AAA, Snowfire, Alex, Dune, Twilkitri (6/10)
Burn Notice: Dune (1/10)- This one is extremely easy if you've seen burn notice, but yeah.
WATCH BURN NOTICE.
Blink 182: Ciato, Cid, AAA, Alex, Dune, Lance (5/10)
Calvin and Hobbes: Elfboy, Snowfire, Alex, Dune (4/10)
Simpsons: Cid, Elfboy, AAA, Dune, Monkey (5/10)
Shadow Hearts 2: Ciato, Cid, Elfboy, AAA, Snowfire, Alex, Dune, Monkey, Lance (9/10)
Devil May Cry 3: Elfboy (1/10)
Bad Boys/Hot Fuzz: Cid, Snowfire, Dune (3/10)
Phoenix Wright: Ciato, Elfboy, Alex, Dune, Twilkitri (5/10)
Wheel of Time: Ciato, Elfboy, AAA, Snowfire, Alex (5/10)
Real American: Dune, Lance (2/10)
Twilight: Cid, AAA, Alex, Dune (4/10)
Happy Gilmore: Ciato, Cid, Elfboy, AAA, Alex, Monkey, Twilkitri, Lance (7/10)
Clue: Cid, Snowfire, Alex, Dune, Lance (5/10)