3 pounds assorted medium to large heirloom tomatoes
1 teaspoon kosher salt, divided
6 thick-cut bacon slices, diced
2 large shallots, chopped
2 garlic cloves, finely chopped (2 tsp.)
6 ounces aged extra-sharp white Cheddar cheese, grated (about 1 1/2 cups)
1/2 cup mayonnaise
1/2 cup chopped fresh basil
1/4 cup thinly sliced fresh chives
1 tablespoon Dijon mustard
1 large egg
Fresh basil leaves
Minced fresh chives
Parmesan Pie Crust
2 1/2 cups all purpose flour
3 ounces Parmesan Reggianno cheese, finely shredded (about 1 packed cup)
1/2 teaspoon kosher salt
1/4 teaspoon black pepper
3/4 cup cold unsalted butter, cubed
1/4 cup cold solid vegetable shortening, cubed
6 tablespoons buttermilk
Preheat oven to 400°F. Cut tomatoes into 1/2-inch-thick slices. Place about 7 or 8 slices (enough to cover top of pie) on a baking sheet lined with paper towels, and sprinkle with 1/4 teaspoon of the salt. Cover with additional paper towels, and reserve.
Arrange remaining tomatoes in a single layer on a lightly greased wire rack set on a large baking sheet. Sprinkle with 1/2 teaspoon of the salt. Bake in preheated oven until wilted and slightly dried out, 40 to 45 minutes. Cool completely, about 1 hour.
Meanwhile, cook bacon in a skillet over medium-high until fat is beginning to render, 4 to 5 minutes. Add chopped shallots, and cook until bacon is crisp and shallots are caramelized, 6 to 7 more minutes. Stir in garlic; cook until fragrant, about 1 minute. Using a slotted spoon, transfer bacon mixture to a plate lined with paper towels to drain. Cool 20 minutes.
Stir together cheese, mayonnaise, basil, chives, Dijon, and egg until combined. Sprinkle with pepper and remaining 1/4 teaspoon salt. Fold in bacon mixture.
Gently spread a third of cheese mixture onto Parmesan-Buttermilk Crust; layer with half of the roasted tomato slices in slightly overlapping pattern. Spread another third of cheese mixture on top of tomato slices. Repeat with remaining roasted tomato slices and cheese mixture. Top with reserved sliced fresh tomatoes, pressing filling gently into crust. Shield edges of pie with aluminum foil.
Bake in preheated oven until filling is set, 40 to 45 minutes. Transfer to a wire rack, and let stand 1 hour before serving. Sprinkle with basil and chives.
Parmesan Pie Crust
Pulse flour, cheese, 1/2 teaspoon salt, and 1/4 teaspoon pepper in food processor until combined. Add butter and shortening. Pulse until butter and shortening are pea size pieces, about 5 times. Drizzle in buttermilk processing until dough begins to just come together. Gather and lightly knead dough into a ball on a large piece of plastic wrap; flatten into disk and wrap tightly. Chill at least 2 hours or up to 2 days.
Preheat oven to 400F. Roll dough on a floured surface into a 15 to 16-inch circle about 1/3 inch thick. Transfer to a 9-inch deep dish pie plate. Trim edges leaving a 1 inch overhang. Fold edges under and crimp. Freeze dough at least 20 minutes.
Line pie crust with parchment paper and fill with pie weights or dried beans. Bake at 400F 20 minutes. Remove parchment and weights and bake until edges are golden and bottom of crust is set, about 8 more minutes. Cool completely about 30 minutes.