So, okay, there was one of my problems.
I don't know if I could have done a better job on that script. Does it matter? Probably not. I think it's Robert Rodriguez who said that every writer has about a half-dozen bad scripts in him that need to be purged before the good stuff can start coming out, and the more I write the more I agree with the sentiment. For whatever it's worth, though, I definitely would not write that script today, despite (or perhaps because of) the fact that I'm a much better writer. I just know that I could not bring that idea off.
Which leads me to wonder: What is a good script for a new writer to attempt? I'm not sure I have a good answer. There are a million pitfalls on the way to a first script, and rather than figure out how to avoid them, many budding screenwriters tend to run straight at them. I can't blame them; I gleefully stuck my foot into dozens of literary bear traps when I was starting out, and it took well over a year to notice the blood on my shoe. Anyway, here are some pieces of advice I would give to first- (or second- or third-) time writers, if they cared to listen to me. The screenwriting equivalent of my "sunscreen" speech, if you will.
1. Don't write about a hitman. I don't know why EVERY SINGLE novice writer has such a yen to do an assassin movie, but... actually, I do know why. It's because they think hitmen are cool. And that's about as far as they get, planning-wise. They think about the "cool" movies that are out there -- Tarantino films, The Professional, Fight Club, etc. -- and the element that seems to tie them together is that the main character is more or less a bad guy. This, they reason, is the shortest path to coolness. What they fail to consider is how much of an uphill battle it is to get an audience or reader to sympathize with someone who kills for money. A more seasoned writer might be able to pull it off; a moderately experienced writer would probably be scared away by the task; a newbie writer just doesn't realize it's an issue.
Once in a great while, someone hits on a good idea for a hitman movie. I think the last one was The Matador. We should all be very, very lucky (and talented) to write a movie that good. It really should have been nominated for Best Picture. And that's what it takes to pull off a sympathetic hitman. Anyone not in that echelon of screenwriting (which is to say, most of us) should stick to protagonists who are naturally easier to like.
2. Write what you know, to an extent. "Write what you know" is a sentiment that's hard to argue with in theory, and there are any number of stories that can be trotted out in its defense. Dashiell Hammett worked for Pinkerton's. Ian Fleming was in the British Secret Service. Michael Crichton is an M.D. Charles Dickens was a child laborer. Well, good for them. (Not so much Dickens, though he clearly turned out all right.) But not all of us has the exact right personal experience to draw from when we're sitting down to pen our latest epic. Does that mean we should avoid completely any story that we haven't lived? Of course not. Quite the opposite, in fact, especially when it comes to screenwriting. In practically every writing class I've taken, there's that one student who's writing a script that is very personal and yes, every single detail really happened, and it's very important that the story be told this way and so on and so forth. I'm sorry, but in the vast majority of cases, no one is going to want to read that script. It might be your story, but it's still a story, and the fact that you lived through it doesn't make a difference to anyone other than you (and maybe your family and friends). A personal story is a great starting point for a script, but to make it a good one you'll need to change it, expand it, compress it, combine characters or create new ones -- and above all, remember that your goal at the end of the day is a good story, not a documentary about your life.
Then again, the flipside is also true. Consider Pulp Fiction. Tarantino was never a hitman, probably never even knew a hitman. He made up all the mob stuff or borrowed it from other movies. But he did grow up in Los Angeles, and every quirk of L.A. life in the movie comes directly from his own experience. Ditto the conversation about Amsterdam and the treatise on foot massages. And by laying a big, made-up story over a variety of personally familiar details, he and Roger Avary wrote a fantastic script. Doing this well is difficult, because those personal details don't fit in just anywhere; shoehorn them in and they'll look shoehorned-in. However, I think it's important, especially as a new writer.
If you want your first few scripts to be worthy of someone else's time, they need to have elements that only you can bring to them. If that isn't the case, and your scripts are only inspired by other movies, then you'll be at a big disadvantage because you're trying to do something that lots of other writers can do extremely well -- and your work will be distinguished only by its inferiority. In other words, if you've never written a screenplay before and you try to write a kick-ass James Bond script your first time out, it's going to suck. (I know. I tried.) But if you write a script about a topic of personal interest to you, on which you have some interesting things to say, then it'll at least have a chance of being worth reading even if the execution isn't totally there.
But that summer you rented a shack by the lake with your friends and smoked a lot of pot and sat around telling dirty jokes -- that doesn't count.
So: why am I harping on the hitman stuff and the uninteresting personal story stuff so much?
Because these are the kinds of scripts written by people who are not really writers.
The dispiriting stuff we hear all the time -- You're writing a screenplay? Oh. Isn't everyone? -- 40,000 scripts registered to the WGA every year -- all that stuff -- it's misleading because it doesn't take into account the massive number of non-writers who try to write screenplays. Check out some of the material uploaded to the peer-reviewing site TriggerStreet.com for a window into this phenomenon. There are tons of people out there that couldn't put together a coherent paragraph if you asked them to, yet are bravely writing 100-page screenplays. I don't want to discourage those people, but at the same time, if you're serious about making a go of it as a writer, you do NOT want to be mistaken for one of them.
If you write a hitman script filled with movie in-jokes, or a talky, rambling tale about breaking up and getting back together with your girlfriend, then you run that risk. The people who read your first script are already armed with a million reasons not to take you seriously; there's no need to throw in a few more.
And, oh yeah, wear sunscreen.