The play begins at “court”, or in the seamy underbelly of Chicago in 1927, when speakeasies and bathtub gin were all the rage. Our hero, Orlando, is stuck doing menial tasks for his brother, Oliver, who keeps him under his thumb, because Orlando has no aptitude for the family business: the numbers racket.
Meanwhile, Duke Frederick is the real kingpin. He too has transformed the family business, taken the chain of family restaurants from his brother (Duke Senior) and sent him packing. Frederick now runs a vast array of gambling houses and brothels, sporting events (wrestling and dogfights), providing a lavish lifestyle for his daughter Celia, and his niece Rosalind, our heroine.
One of Frederick’s employees is a bear of a man named Charles who wrestles, and rarely loses. Orlando’s dastardly brother Oliver arranges with Charles to take out Orlando in a match. But when the contest actually happens, it is Orlando who comes out on top, dazzling Rosalind with his prowess, and so the love story begins.
But Frederick doesn’t make it easy. He loses his cool, and tells Rosalind she has to clear out of the city, or else. Frederick’s own daughter Celia is so attached to Rosalind, the two of them vow to leave this sordid place and seek peace elsewhere. They convince Touchstone, Frederick’s favorite stand-up comedian, to go with them.
There’s a parallel story in Orlando’s life. Brother Oliver plans to burn Orlando’s hovel to the ground with him in it. Orlando and Adam, the faithful servant, similarly escape from the clutches of a lifestyle they’ve both grown to hate.
Enter The Forest of Arden, now located in the upper peninsula of Michigan, hidden from the reach of Frederick. The benevolent Duke Senior leads his merry band of players to discover the joys of living in the wild, including Jacques, a melancholy philosopher, and Amiens, a calming force with an almost ethereal voice.
Unbeknownst to Rosalind and Orlando, they are both making their way to the Forest, with Rosalind dressed as a sweet-faced boy named Ganymede. This disguise yields some of the sweet comedy of the play, as she meets up with the forest folk, a homespun lot.
But when Orlando starts posting love poems on trees to his “very, very Rosalind”, the real fun begins. Ganymede convinces Orlando to woo him/her as if he/she really was Rosalind (which, of course, she is).
While Orlando’s education proceeds, everyone else seems to be falling in love too. Touchstone lusts for Audrey, Silvius is deeply in love with Phoebe who in turn has fallen for Ganymede. Brother Oliver comes to the forest on a deadly mission and is transformed and woos Celia. The play ends with four weddings, presided over by the voice of Amiens (originally written as the god of marriage). And then they dance. The Charleston!