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For Len Jenkin, an award-winning but difficult American playwright, two qualities essential to theatre are wonder and heart. Taking these terms, this article examines two perplexing plays that by incorporating material from the Grail story provide entrance to his theatre. Dissolving and interpenetrating scenes in Dark Ride can be disorienting, yet the action is clear. The characters are drawn into a quest that brings them to a convention ballroom where a thief places a stolen precious stone on a pedestal around which the characters stop dancing. Since another Jenkin play utilizes material from Wolfram von Eschenbach’s Parzival in which the Grail is a precious stone, one can interpret the ballroom gem as a Grail image that functions in Western literature as a motive for questing. Despite the lack of heart, because character interaction is minimal, the play has the wonder of questing. Poor Folk’s Pleasure is a series of scenes in which characters interact, sing, and dance within a framework in which a boatman with a “beatific smile” arrives, but when none board his boat leaves. Since a miraculous vessel that transports questers on their adventure appears in the anonymous Queste del Saint Graal, one can interpret the boat as the miraculous ship in the Grail legend. Despite the lack of wonder, because the characters do not undertake the quest, the play has the heart of pleasure. Thus the two plays complement each other with each one dramatizing just one of the two essential qualities of theatre. Other Jenkin plays, however, dramatize the two qualities integrated. By paying attention to the presence or absence of quest and pleasure therefore, the critic can begin to appreciate Jenkin’s theatre of wonder and heart.