---MAJOR SPOILERS BELOW ---
1. Marion Crane, Psycho (1960) - Neato! It's 1960, and I'm at the movies. I'm really enjoying this movie called Psycho, even if it is in black and white. I like Janet Leigh, and I'm happy to see that she is the star of this movie! Also, my boner is happy about her bra. I'm so glad she plans to return that money she stole, right after she takes this much-needed shower. She needs to clean up! Literally, but also metaphorically. Wait...what the...what the fuck? Who is that with the knife? What the fuck just happened? She's DEAD? You mean I have to spend the rest of the movie with the odd fucker who won't shut up about birds? Oh, wait. This movie is still awesome. That doesn't change the fact that my world has been rocked by the surprise murder of someone I cared about. At least I can take solace in the fact that JFK is still president. Phew.
2. Dr. Malcolm Crowe, The Sixth Sense (1999) - That's salty, dawg.
3. Vincent Vega, Pulp Fiction (1994) - Travolta's hitman was the main character of the movie. Plus, he's alive even after he dies, because this was the mid-'90s and THERE WERE NO RULES. This is why I coined the phrase "It's time to shit or get the Pop-Tart. Or get machined gunned to death by Bruce Willis."
4. Optimus Prime, The Transformers: The Movie (1986) - The lead Transformer is killed a third of the way into this children's cartoon/toy commercial. When Optimus Prime is shot and killed while trying to open the Autobot Matrix of Leadership, it was like my childhood was shot and killed while trying to open the Autobot Matrix of Leadership.
5. Russell Franklin, Deep Blue Sea (1999) - It was only a matter of time before all of the characters in Renny Harlin's mentally-challenged thriller were killed by the Alzheimer sharks, but none of us were expecting Samuel L. Jackson to be among the first, or for it to happen right before he made his big speech. Apparently, the Alzheimer sharks were as sick of Sam Jackson monologues as the rest of us had become by the late '90s. Fuck that guy.
6. Lt. Colonel Austin Travis, Executive Decision (1996) - Of course the leader of the military mission has to be taken out in Stuart Baird's surprisingly good Executive Decision, if only so Kurt Rusell can step up and channel his inner Jack Burton. But it's Steven fucking Seagal, so we don't expect it. I choose to believe getting sucked out of airlock didn't kill him. I choose to believe that ponytailed sonofabitch can fly.
7. Special Agent Richard Chance, To Live and Die in L.A. (1985) - William Friedkin's synth-heavy, neon-drenched crime thriller is dated but awesome and way underrated. There's a kick-ass car chase and some neat stuff about counterfeiting. Willem Dafoe plays a villain who's incredibly slimy (because Willem Dafoe) and William Peterson is great as a jacked-up, twitchy federal agent. Then, with 15 minutes left in the movie, Peterson takes a shotgun blast to the face and the fucking hero of the movie is dead. For 15 minutes, John Pankow -- aka Cousin Ira from Mad About You -- is the hero of a Hollywood action movie directed by an Academy Award winner.
8. Jenna, Friday the 13th (2009) - This slick, pointless "remake" of Friday the 13th should definitely fuck off, particularly for killing the character who, by every indication, would be the "final girl" to fight and defeat Jason. She's played by Danielle Panabaker, who is lovely and also was in Sky High (she lives in that one, because it does everything right) and is the best thing about the movie. I want Hollywood to remake me barfing on this.
9. Wash, Serenity (2005) - It must suck to make it all the way through a TV series (Firefly) and most of its spin-off film, only to be unceremoniously impaled on a harpoon, but that's precisely what happens to Alan Tudyk's Wash three-fourths of the way into Serenity. It really shouldn't be a surprise, because Joss Whedon has an almost compulsive need to kill off his characters -- particularly the ones fans like -- but the suddenness with which Wash's death occurs puts it on this list. Alan Tudyk should be harpooned in more movies.
10. Tracy Mills, Se7en - Because what's in the box? What's in the boooox??
11. John Baxter, Don't Look Now (1973) - Nicholas Roeg's offbeat horror movie dicks us around for two hours just so we can be surprised when Donald Sutherland is stabbed to death by a little person. At least he got to go out boning Julie Christie. For real, apparently.
12. Billy Costigan, The Departed (2006) - It probably wasn't a surprise to anyone who saw Infernal Affairs, but those of us unwilling to sit through a movie with subtitles (because learn English) couldn't have predicted what would follow Leonardo DiCaprio's line, "I am killing you." Irony! Irony and rats.
13. Ted Treffon, Burn After Reading (2008) - Sure, Bradd Pitt's Chad Feldheimer is a more obvious choice for this one, because he's a bigger star and his murder is more sudden. But seeing as gym owner Ted Treffon (the great Richard Jenkins) is the only sympathetic character in the Coen Brothers' movie, it's something of a surprise when he is brutally murdered with a hatchet by John Malkovich. Not cool, Teddy KGB. Flop the nut straight. Don't splash pot. I must break you. Oreos.
14. Jack Vincennes, L.A. Confidential (1997) - Another example where it's no so much the fact that the character is killed but more so the moment at which it happens. Kevin Spacey's final line to the newly-revealed bad guy is one of cinema's great "fuck yous." So is K-PAX.
15. Richard 'Dick' Brewer, Young Guns (1988) - Chuck Sheen is the first to die in Young Guns, presumably so he could go back to his trailer and inhale cocaine from atop a stack of dead hookers and older, leftover cocaine.
If you've got a good surprise character death that was left off this list, leave it in the comments below. Needless to say, spoilers. Let's ruin every movie for everyone!