Starting 7/19/24, 6:30:00 pm: Don’t Let the Pigeon Drive the Bus!

Waitress Pineapple Upside-Down Pie

TCR is proud to present the regional premiere of the smash Broadway and London hit, Waitress! Featuring music and lyrics by Grammy Award® winner Sara Bareilles and book by acclaimed screenwriter, Jessie Nelson, Waitress promises to be little slice of heaven this summer.

Jenna, a waitress (and expert pie-maker) dreams of a way out of her small town and rocky marriage. A county baking contest — and a handsome new doctor — offer her a tempting recipe for happiness. Supported by her sweet and sassy crew of fellow waitresses and customers, Jenna’s tale reveals the power of friendship and the courage to take chances.

Inspired by the beloved independent film and brought to life on Broadway by a groundbreaking all-female creative team, Tony®-nominated Waitress is cherished by audiences all over the world. Waitress offers a special recipe for finding happiness in unexpected places. It will move, uplift and inspire!

Tickets start at just $27 and are available HERE

Pineapple upside-down pie

(Makes One 9-Inch Pie)

Classic Single pie crust

  • 1¼ cups unbleached all-purpose flour
  • 1 tablespoon sugar
  • ½ teaspoon kosher salt
  • 8 tablespoons (1 sticks) unsalted butter, cut into small cubes and chilled
  • 3 to 4 tablespoons ice-cold water


  • 2 tablespoons unsalted butter
  • ¼ cup lightly packed brown sugar
  • 4 slices canned pineapple: 3 cut in semicircles, 1 left whole
  • 6 maraschino cherries, halved
  • ¾ cup unbleached all-purpose flour
  • 1 teaspoon baking powder
  • Pinch of kosher salt
  • 3 tablespoons vegetable shortening
  • 1/3 cup granulated sugar
  • 1 large egg
  • 1 cup whole milk
  • ½ teaspoon pure vanilla extract

For the Filling

Preheat the oven to 400°F. Place the butter in a shallow 9-inch pie pan and put the pan in the preheating oven to melt the butter, 5 to 7 minutes. A pie pan with at least a ½-inch lip edge works well, so there is room to crimp the crust edge onto the lip, creating more of a crust surrounding the edge when the pie is turned over.

Sprinkle the brown sugar evenly over the melted butter. Place the whole pineapple slice in the center of the pan and arrange the half slices around it. Fill in the gaps with cherry halves, cut side down. Set aside.

To assemble the cake batter, sift together the flour, baking powder, and salt in a medium bowl. In another bowl whisk the vegetable shortening and granulated sugar together until light and fluffy. Add the egg, milk, and vanilla and whisk until incorporated. Add the dry ingredients to the batter slowly, whisking just until combined.

Pour the batter into the pie pan, being careful not to dislodge the fruit. Smooth the top of the batter.

For the Crust

Roll out the pie crust and carefully lay it over the cake batter. Crimp the edges, creating a seal around the edge of the pie pan and fully enclosing the cake batter.

Bake for 10 minutes, then reduce the heat to 350°F and bake for 20 to 25 minutes longer, or until a toothpick inserted into the middle of the cake (through the crust) comes out clean.

Immediately place a large plate over the top of the pie, and carefully invert the plate and pie pan. Leave the pie pan in place for 10 minutes, then remove the pan slowly to reveal your Pineapple Upside-Down Pie! Let cool completely before slicing and serving.

© The Waitress Pie Book, by Daniel Gercke and Sheri Castle