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Bittersweet Ending: Theater
  • The Phantom of the Opera: Christine gets her Tenor Boy Raoul, leaving the Phantom alone and miserable.
    • Love Never Dies: It turns out that Christine loved the Phantom more all along — her son Gustave is the product of a one night stand they had before she married Raoul — and Raoul accepts this. Unfortunately, Meg Giry, driven mad by the Phantom never paying attention to her and being unaware of how much she did to build his fortune in America (she was forced into prostitution by her mother) tries to murder Gustave. When the others confront her, Christine is accidentally killed...but she dies in her true love's arms and Gustave is ready and willing to accept the Phantom as his father, so he is no longer alone in the world.
  • A Chorus Line: Paul is injured with a 50/50 chance of ever being able to dance again. And only some of the dancers will be accepted into the chorus line; the others have to go. In both cases, such is the reality of show business.
  • Wicked. Even though the protagonist survives, and Glinda banishes both Morrible and the Wizard, Glinda is still left alone believing every close friend she's ever had to be dead. Fiyero, now cursed as a scarecrow, and Elphaba might have survived but can never return to Oz. Glinda and Elphaba come to terms with the irreversibility of fate and circumstances and ultimately realize that the fact that they met and changed each other was what really mattered.
    • At least it's not so much of a downer ending for Elphaba and Fiyero compared to the book(s).
  • In the musical Spring Awakening, Melchoir finds that his pregnant friend, Wendla, is dead. Racked with guilt, he attempts to commit suicide only for her ghost, and his friend's ghost, to appear and convince him to live.
    • Even more creepy, in the original play. Mortz's ghost finds that he rest with a pride and a smile on his face, while Melchior, remorseful of his part in Wendla's death, lives on under the workds of the Masked Stranger.
  • By the end of Act II in "Into the Woods", only Cinderella, Little Red, Jack, The Baker and the Princes with their new wives end up surviving the Giantess' Roaring Rampage of Revenge.
  • Gilbert and Sullivan's The Yeomen of the Guard ends with one happy couple and poor Jack Point realizing his love is well and truly lost to him.
  • 1776 ends with the Continental Congress signing the Declaration of Independence-with the knowledge that they have a long, arduous war that they have little chance of winning to look forward to, considering their army is a shambles and the British Navy was the greatest in the world. Hindsight tells us they'll win eventually (since it is based of history), but they don't know that.
  • Cyrano de Bergerac: Roxane knows the truth of Cyrano Playing Cyrano for Christian and assures the dying Cyrano that she will mourn him, De Guiche discovers that is Lonely at the Top, Roxane realizes that she has been Loving a Shadow for fifteen years and that all her suitors abandoned her or are dead, Ragueneau not only doesn’t cook anymore, but he never could keep a stable job and is very angry because Molière stole a scene to Cyrano, and OnlySaneGascon Le Bret rebels against destiny, because he never understood the self – destructing tendencies of his best friend, he could do nothing to help him .
  • The climax of Shakespeare's Henry V sees the vastly outnumbered English defeat the French at the (in the play) decisive Battle of Agincourt. The victorious Henry charmingly woos the French Princess Katherine to seal the deal. But the Chorus reminds the audience that "this star of England" would die just a few years later, and his son, unfit to rule, would lose France and "make his England bleed."
  • Although it's usually considered tragic, Romeo and Juliet finishes with the ending of a terrible feud which was probably going to have killed a lot more than five people over the years had it been allowed to continue.
  • Nathan of Thrill Me does get his parole, and so gets to go out and live his life. However, there are only two characters in the show, and this makes it look like the only meaningful relationship of Nathan's life was with Richard, who is now dead. The ending can be played better or worse—anywhere from Nathan still being fully obsessed with Richard to Nathan finally beginning to get over him—but regardless, Nathan gave up most of his young life to a bad relationship, and only now gets any chance at starting over. Not to mention the fact that a convicted murderer being set free isn't necessarily the best ending.

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