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August
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With his company in deep financial trouble, Tom now tries to mooch off of Joshua, by giving him a load of hooey about how they'll make it through the lock-up period and be able to cash in.  I don't know how he thinks there'll be a pile of money waiting, though, as company shares are worth less than used copies of Pearl Harbor, something Josh Hartnett knows about.

        After successfully conning his brother, Tom visits his parents, I suppose, to continue spreading his joy.  As soon as I saw Rip Torn in the role of the father, I immediately wished he'd revert to his Dodgeball character and nail Tom in the face with a wrench, but alas, no.  Dad calls Tom on the carpet, stating that he visited the LandShark offices and saw nothing but a bunch of kids sitting around eating Oreos.  He tries to ask his son in a polite way what the hell his company actually does, but instead of finally explaining it, Tom has a tantrum.  He calls his father a failure despite being a tenured professor who seems financially secure.  Mom tries to smooth things over, but Tom admonishes her: "Mom, I'm saying something to Dad and I'm not finished yet!"  He then brags that 'Tiananmen Square' was just 'the fax machine', which one can't argue with, if only because we can't understand his point.  Tom leaves in a huff and I assume his parents will spend the rest of the night wondering why they didn't give him some sorely needed beatings as a child.
Tom coldly spent his brother's last hundred shares on a pinball game.
Dad gloated, knowing his suspender-factory idea wasn't looking so bad now.
Continuing on his mission of moaning, Tom visits the bar where Sarah the ex works.  He convinces her to go get a bite to eat and they exchange some vapid chatter about her architectural studies in Spain.  Culture is a big interest of hers but we never figure out how she ever had an interest in Tom.  Tom wants to get kissy with her before calling it a night but she hesitates, leading to him having another tantrum.  I wish they'd just move things along so we can finally see this jackass get his comeuppance, hopefully he'll borrow and forget to pay back some mobsters and they'll put his head in a vise.  I doubt it though, as that would be far too exciting to be in this film.  

        At the office the next day, Tom bitches his employees for slacking off work, though I still can't figure out what there is for them to work on.  Of course, Tom has slacked off more than anyone else, having to be reminded that he's scheduled to appear at a symposium that day.  Tom and his assistants walk into the place in slo-mo, an effect that usually builds up hope that something important is about to happen but then again, this is August we're watching.
"Get back to work spamming our crap movie on message boards!"
        Tom walks out on stage.   Having nothing at all prepared to say, he lays on the arrogant blabber, saying stuff that would sound profound to a four-year old like "Are we making the world less sucky or more sucky?" as if that question hadn't already been answered.  Tom contradicts his former beliefs, pointing out that the new techie companies are simply tools of the big old companies.  We get perhaps our biggest shoehorn of the film when Tom compares companies to eyeballs if only to work in a reference to Un Chien Andalou
        Tom does something positive for once when he praises Joshua, for being 'magic' in his computer expertise.  He then has a fit, blaring that startups are over, convergence is over, dotcom is over, blah blah blah.  The reasons behind the tech collapse were common knowledge well before August 2001, when this story takes place, but it seems not to have occurred to Tom until this moment.  Because the script says so, the young hairy masses in the audience give Tom a standing ovation.  After the speech, Tom reverts to his usual dickwad self.  He brushes off Joshua's mentioning of his newborn's cold to ask him what he thought of the speech.  Assistant Dylan thought it was impressive, so I have no idea what in hell he was looking at. 

        At his apartment, Tom prepares dinner for himself and Sarah, who obviously suffered a serious head injury, as she agreed to come over.  They share some allegedly cute banter.  Sarah points out she saw his face on the cover of Wired magazine.  Tom says "I hated that picture.  I looked like a total douchebag" which lets us know that Wired has solid photographers.  He admits that his company is headed down the tubes and acts like a human being for a couple of minutes, so Sarah gives him some sympathy booty.

        Dylan, Melanie and Tom attend a meeting with a woman the next day to discuss a possible buyout of some of LandShark's stock.  Tom is back in mope mode, so I guess he's having another of his monthly 29 day-long PMS attacks.  He doesn't say a word or even shake hands with the woman.  As he walks through the LandShark office looking for Joshua, I notice some guy putting up a big picture of a shark swimming in water, so even the company's picture makes no sense.  Joshua wisely avoids Tom and another potentially lame speech.  Tom also disappoints Sarah, as he shows up way late for an architectural show she was putting on, so Joshua and Sarah have apparently joined me in the "Couldn't give a shit about Tom" club.
"I was gonna put my portrait in the living room, but my guests would fall asleep."
        Tom drives around and pouts for the... I mean, he continues to pout.  Good son Joshua has dinner with the folks and laughs to himself at the small Buddha statue delivered to them as a gift from Tom.  Soon enough, Tom shows up to piss on the party.  He is here to make amends for acting like a dick to the family, though his apology to his parents doesn't quite bring us to tears: "You want the words?  I'll say them.  I'm sorry, I apologize, my bad."  Joshua calls his brother on the carpet, using Tom's words to call the Buddha gift "B-list" and "It's so third-quarter '99".  For once, this film came up with a scene to entertain me but its too late in the proceedings for things to start getting interesting now.
        Outside, Tom pours his heart out to Joshua, admitting that the numbers for their company don't add up, how LandShark can't make money and how "our market doesn't exist", which was always obvious to me, as people have yet to become interested in buying nothing.  This is all supposed to be some kind of epiphany for Tom, I guess, even though all the things he says were common knowledge well before August 2001.

        Later the same night, Tom starts to... I mean, continues to mope, this time in a bar, where he bores the bartender with more deep-sounding but dense dialogue such as "Ultimately nobody wants everything", the sort of lines you would expect to read in a friendless high school freshman's diary.  He sees some other dot-com guy with a trophy girlfriend.  DrunkenTom starts bitching at the dot-com guy for, I suppose, being like himself while also getting rude with the girlfriend.  Finally, the dot-com guy does what everyone else in the film should've already done and clocks Tom in the face.  Maybe we're supposed to feel Tom's regret for mouthing off but I only regretted that Tom didn't wander into Henry Hill's bar from Goodfellas and receive the Billy Batts treatment.