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On Tragedy
At a meta-level, tragedy is optimistic because it enriches its audience by helping it understand a philosophical principle essential to man's well-being. The events leading up to a tragic death tend to call to attention one's own tragic makings, growing the audience's self-awareness and giving it hope that such pitfalls as beset by the fictional character may be avoided in his own life. With the final act of death upping the ante, the lesson is seared into the soul of the audience, increasing the odds that that lesson will actually change his life.
A tragedy may appear outwardly cynical or dismal - consider the deaths of Romeo & Juliet, Oedipus, or Lester Burnham (American Beauty) - but underlying each instance of death is a sense of perfect closure - of death being the best possible exit of the character from the stage, a high-stakes demonstration of a philosophical principle at work in a concrete, believable scenario.
In Romeo and Juliet, death is self-inflicted out of despair at the loss of love. That Romeo and Juliet consider their mutual love so essential to their valuation of existence is the message: that a life without love is not a life worth living. And what's not to find uplifting in such an exaltation of what is arguably man's greatest principle or emotion?
Oedipus suffers under the hands of the Gods who punish him for his hubris. Justice levels even the greatest of kings, causing him to sleep with his mother and tear out his own eyes. That we are all held to the same standards of morality and decency, no matter how rich or beautiful or powerful, makes us feel equal, and therefore more connected, to one another.
Lester Burnham commits the sin of not treating his own life with the same respect with which God granted it. But he eventually wakes up and realizes that he's been squandering it, prostituting it to the greed of others. He's sleep-walked through his marriage (an institution of love, that sacred human and spiritual principle exalted in Romeo and Juliet) and the miracle of creation of his own daughter. He realizes that he's not ready to meet his maker, that he hasn't expressed adequate gratitude for "every little stupid moment of my life" and then proceeds to prepare for death, which he naturally meets with at movie's end, immortalizing that perfect moment in which he basks in his own realization of living in the 'ongoing wow' of existence.
So sad endings are often always happy on some higher level than their surface action might otherwise suggest. I think the big difference is that death is simply just an artistically superior ending in the case of high-stakes philosophical principles, while a party or two people getting together may serve to close smaller or more subtle ideas more appropriately.
Above this level, of course, is that the concept of tragedy is itself optimistic: that the human lot can be improved through artistic endeavor. That we allow ourselves to affect and be affected by the joys and despair of our fellow man by creating and experiencing art. And that, ultimately, we are a beautiful species, capable of as much good and excellence as we are of the cheap, amoral and stupid behavior that tragedy places under the magnifying glass.
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