Amish Tomato Pie

Preheat oven to 425°F (220°C) with a baking sheet on the lowest rack. (5 minutes)

Press pastry into a 9-inch deep-dish pie plate. Cover with two layers of aluminum foil, then add pie weights or dried beans. (5 minutes)

Slice heirloom and Roma tomatoes into 1/2-inch-thick rounds. Remove seeds with your fingers and discard. Transfer six heirloom slices to a paper towel-lined plate; cover with more paper towels and set aside for decorating the pie. Arrange remaining heirloom slices and all Roma slices on a wire rack. (20 minutes)

Place pie crust onto the baking sheet in the preheated oven. Place the wire rack with tomatoes onto a higher rack. Reduce the oven temperature to 400°F (200°C). Bake until the bottom of the pie crust has lost its translucent raw look and the edges have just started to color, 12 to 15 minutes.

Leaving tomatoes in the oven, remove pie crust and carefully lift out the foil and weights. Cover the edges with foil to prevent them from burning. Poke bottom of crust several times with a fork to keep it from puffing up. Return pie crust to the baking sheet and bake until light golden brown on the bottom, about 8 more minutes. Remove from the oven and let cool. (10 minutes)

Continue baking tomatoes until wilted, 15 to 20 more minutes (for a total of 40 minutes). Remove from the oven and let cool for about 15 minutes; keep the oven on. (40 minutes)

While the tomatoes are cooling, cook bacon in a large skillet over medium-high heat, turning occasionally, until some of the fat has rendered, about 5 minutes. Add leek; cook until bacon is crisp and leek is soft and brown, about 5 minutes. Transfer mixture to a paper towel-lined plate and let cool, about 5 minutes. (15 minutes)

Combine Cheddar, Fontina, mayonnaise, basil, egg, Dijon, salt, and pepper in a bowl. Add bacon-leek mixture and mix until well combined. (5 minutes)

Spread 1/3 of the cheese mixture into pie crust, then arrange 1/2 of the roasted tomatoes over top, alternating heirlooms and Romas; repeat layers once more. Spread remaining cheese mixture over top, then gently press in reserved fresh heirloom slices in a decorative pattern. Cover the edges with foil, leaving tomatoes uncovered. (15 minutes)

Bake until browned and bubbly on top, about 40 minutes. Let cool completely before serving, about 1 hour. (1 hour 40 minutes)