Dan: I file Kevin Smith in the same mental folder as I do Quentin Tarantino, mainly because they both like to focus on dialogue. The difference is that Quentin mixes his bla bla with action where as Smith mixes in comedy. Now I am sure others might disagree at the mere idea of those two directors sitting at the same table together, but that's just how their films strike me personally. I like them both, but on the whole I find Smith more approachable to a layman audience. You can enjoy Mallrats without "getting" Kevin Smith, but Jackie Brown is pretty tough jerky to chew if you don't know who's sitting behind the wheel.
My two cents out of the way, here's how and why the points landed where they did.
The first point went to Chris with his excellent observation of the scope of Dogma. Kevin Smith could have done nothing but poop and fart jokes, settling into the same suck that Adam Sandler finds himself recently. Clerks proved that he knew how to direct and write, and that's all he needed to line his pockets. But, like the true artist and cool guy he is, he decided to write a movie that not only made some wildly funny observations on organized religion, but also left you having serious debates afterwards. It also helped that it had Alan Rickman.
Kyle fights back and snagged a point with the attainability of Clerks. Everyone who's ever fantasized about making it big in Hollywood thought, "I wonder if I should just go for it, max out my credit cards and take a chance?" Every time we hear a story of someone who took that plunge and succeeded, it gives us hope that we could do it too. Kevin Smith making Clerks was an inspiration due to how meaningful the movie was yet how simple it was to make. "Write what you know" is what we're all told, and Kevin Smith must know some very intimate truths about us all, because that's what he wrote.
I considered not giving Kyle the third point simply due to the similarity to the second point, but upon further reflection I decided to split the two. The first one focusing on the achievement on the whole, with a very indie filmmaking vibe, this second point for Kyle focused more about why the movie store and convenience store was simultaneously the only location available to Smith, and the only locations that would ever have worked. Robot Chicken, Family Guy and a plethora of others have shown us that simply mentioning pop culture existed in the past will get you an audience. Smith realized that a movie store would have instant access to infinite references that he could pull upon, and the convenience store could represent a job that was immune from the possibility of being helpful to society. Any hack director could have made references to movies, and then had a plot shoehorned in to fill the time, but Smith was smart. He wrote a story about the type of people who care about film references, really care about them. And in that caring about the non-important, and lamenting the lack of success of the real, Smith touched an entire generation. Heck, the movie holds up because gen Y feels the same way.
Chris snagged another point for his side during the drinking round by having Dogma be the shining example of what an indie filmmaker can do with a serious subject and a bigger budget. It's true that Clerks was Smith's first, so there is no way to see any progression in his craft, and that's a built in weakness. Especially for Smith, who likes to reuse actors, characters and plotlines, Clerks has to start from ground zero. Jay and Silent Bob Strike Back is pants-on-head hilarious in the parts when it references other movies in Smith's lineup; Hell, it references Dogma. Clerks can't reference any other work due to time flowing forwards, and so one of Smith's best tools was unavailable. Sad panda.
Finally, and for the win, Kyle reminds us that when you turn off the CG, get rid of the larger, better known cast, and cut things down to just conversation in a movie store, you better bring the jokes. Clerks brought the jokes, simple as that. Dogma had the poo monster, flying Ben Affleck, and the like. That's all budget, and without it I don't know if Dogma would be as good. You can't take anything away from [I]Clerks[/i], and that is why it wins.