Chris Rock had a quote a while ago, and it's about movies, not games, but I think it applies. It went something along the lines of (and I'm paraphrasing) "When you're doing dramatic work, critics and fans will give you points for effort. With comedy, there's no A for effort. It's funny, or it isn't."
Any comedy writer will tell you that writing a successfully comedic story is an intensely difficult, and often frustrating experience. That's coming from someone who does comedy professionally. Game developers, by and large, aren't comedians. Hence why comedy in gaming is rarely attempted, and so often falls flat when it does. Often when games are funny, it's because outside writers are brought in, ala The Simpsons game and the like. Because let's face it: just because a dev team might have a few funny guys on it, that doesn't mean they can write jokes or have any sense of comedic timing. In fact, most times they flat-out don't.
Obviously there are those rare gems that remind you comedy in gaming is not only possible, but potentially plentiful. Tim Schaefer is an obvious pick, but there are others. The guys behind Portal, for example, and the current Sam & Max team seems exceedingly talented as well.
Again, comedy is just a challenging undertaking, possibly more so than standard dramatic fare, and it seems like most game developers aren't necessarily up for the task at this point. Here's to hoping that changes eventually.
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