I am thinking about nominating this article for VFH, and I just want to see if it's funny enough and what I need to work on. I think it's a cool article already. By the way, Josh Server is very notable; he was one of the original cast members on All That and to this day is the longest-running cast member in the show's entire history.
Ok, I'm only a N00b here, so my views might be a bit out of focus from everyone else here, but for me this article in its current state is not what I would call particularly funny. It has a few good lines, I liked the one about him claiming to invent the internet, but for me its rather light on gags... I would suggest that you think about removing maybe one or two quotes from the top, as you have a lot there, and I'm not sure they all add to it that much. But hea, I'm British, what do we know about humour? (humor??)
Again (perhaps only for me) this is not really a particularly original concept as it's just basically making fun of the guy, but not from any particular perspective or with any real concept to make is stand out. Perhaps it might work better and be a bit more original if you combined some of the work you have done here with another idea, maybe linking to a particular person who was involved with him on a regular basis, or something he did. Quite what that idea is? Well, that's your job...
Prose and formatting:
I think the language you have used is a little broken in places, especially the After graduating high school in 1982 at the age of three, Josh Server, who skipped a few grades and (at the time) suffered from a rare age disorder similar to Jack, lost interest in nerdy things, removed his glasses, got LASIK, and became addicted to the Next Big Thing at the time... Nickelodeon. paragraph. For me that's a lot of commas to put all together! I think that most of the article suffers from this, if to a lesser extent. I think that the article would benefit greatly if you were to go through trying to reduce the number of words which you use to say what your trying to say. This would make it read a lot better, and make it more enjoyable.
The pictures work quite well at times, and fit with the text. I think they are laid out quite well and that you have about the right number of them. I might suggest that you make the "Josh Server from his 1982 yearbook" picture bigger? Looks like you have space for it, so I see no reason not to.
In answer to your question, and based on its current form I would advise against putting it up for VFH. I have something there myself, so I know how harsh people can be. You have obviously put a fair amount of thought into the article, so I think it can "make it" one day if you wish to work on it more, but I think it needs quite a substantial amount of more work... If you fancy doing it, good luck!