Once Upon a Mattress takes place in a fictional medieval kingdom ruled by the devious Queen Aggravaine and the mute King Sextimus the Silent. King Sextimus suffers from a curse that can only be reversed "when the mouse devours the hawk." As the show opens, the populace of the castle complains about an unjust law levied by Queen Aggravaine. She is testing Princess #12; to the queen's delight, the princess misses the last question ("What was the middle name of the daughter-in-law of the best friend of the blacksmith who forged the sword that killed the beast [the dragon killed by St. George]?") and is given a dead bird. The law states that no one may wed until the Prince, Dauntless the Drab, first marries ("throughout the land no one may wed, 'till Dauntless to the altar's led") . However, every petitioning princess is sent away after failing an unfair test devised by the Queen. It seems that no one is good enough to marry Prince Dauntless.
The crisis escalates when the leading knight of the realm, Sir Harry, discovers that his girlfriend, Lady Larken, is pregnant. Facing great embarrassment and loss of his station, Sir Harry embarks on a quest to find the last princess in the realm. He soon returns with Princess Winnifred the Woebegone, a brash, unrefined, and muscular princess from the marshlands. She immediately charms Dauntless and most of the townspeople. However, she also succeeds in offending the Queen, who vows to find a way to stop her.
The Queen, assisted by her Wizard sidekick, quickly designs Winnifred's secret "test." They will place a tiny pea beneath twenty thick downy mattresses. If Winnifred is unable to sleep due to the pea, then she will be sensitive enough to marry Dauntless.
As the day of the test approaches, Dauntless and Winnifred fall in love, Harry and Larken break up (only to be later united by Winnifred), and the King, Jester and Minstrel trick the Wizard into telling them of the test. When she finally takes the test, Winnifred cannot fall asleep. She drowsily confronts the Queen the next morning, but Aggravaine insists that the test was rigged. Dauntless tells Aggravaine to "shut up," and the curse on King Sextimus is lifted (the "mouse," or Dauntless, thus devours the "hawk," or Aggravaine). Aggravaine discovers that she cannot talk, and Dauntless and Winnifred are free to be married. The Wizard falls for the King's charm and wit, and leaves the poor Queen hopelessly hopping and skipping on stage.
In the final seconds of the play, the real reason why Winnifred passed the test is revealed. After learning about the test, the King, Minstrel, and Jester stuffed the mattresses full of weapons, jousting equipment, and other sharp items. All the items are removed by the Jester in the Finale. After the items are removed Winnifred still has trouble sleeping until Dauntless takes the pea out from under the mattress, when she then falls asleep almost immediately. Everyone, in classic fairy-tale tradition, lives happily ever after.
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