Hey, this is kind of random but my high school just had a senior symposium of alumni in various careers including speakers from the entertainment industry. One woman, an author, Amy Sohn (class of '91) brought up an anecdote about someone from the year above her and how he was voted "Most Likely To Be Homeless." She pointed out the irony of his position as supervising producer on LOST. Anyway, I didn't want to say what HS I go to, but apparently it's the same one you attended, which I thought was rather interesting (read: "pretty damn cool").
p.s. She said that you threw crazy parties and were nicknamed "the scoop." Sound familiar?
Take care, fellow alum! lol