Step 1: Prepare Your Tomatoes. Slice tomatoes about 1/4 to 1/2 inch thick. Arrange them in a single layer on a cooling rack set over a baking sheet or in a colander. Sprinkle liberally with salt and let them sit for at least 30 minutes, up to an hour, to draw out excess moisture. Gently pat them very dry with paper towels before proceeding.
Step 2: Blind Bake the Pie Crust. Preheat your oven to 400°F (200°C). If using a homemade crust, roll it out and fit it into a 9-inch pie plate. Trim and crimp the edges. Prick the bottom and sides with a fork. Line the crust with parchment paper and fill with pie weights or dried beans. Blind bake for 15-20 minutes, or until the crust is lightly golden. Remove the weights and parchment, then bake for another 5-7 minutes until the bottom looks dry and slightly golden. If using a store-bought crust, follow package directions for blind baking. Reduce oven temperature to 375°F (190°C) after removing the crust.
Step 3: Prepare the Herb Layer. While the crust bakes and tomatoes drain, chop your fresh basil. Set aside.
Step 4: Mix the Cheesy Topping. In a medium bowl, combine the mayonnaise, shredded cheddar cheese, Monterey Jack cheese, minced garlic, black pepper, and a pinch of salt. Mix well until thoroughly combined and creamy.
Step 5: Layer the Pie. Once your pie crust is blind-baked and the tomatoes are dry, begin assembling. Place a layer of the drained tomato slices in the bottom of the pre-baked pie crust. Sprinkle about half of the fresh chopped basil over this layer. Repeat with another layer of tomatoes and the remaining basil.
Step 6: Add the Cheesy Topping. Carefully spread the entire mayonnaise and cheese mixture evenly over the top layer of tomatoes, ensuring it reaches the edges of the pie crust.
Step 7: Bake the Tomato Pie. Place the pie on a baking sheet and bake in the preheated 375°F (190°C) oven for 35-45 minutes, or until the topping is bubbly, golden brown, and the tomatoes are tender.
Step 8: Cool and Serve. Remove the tomato pie from the oven and let it cool on a wire rack for at least 20-30 minutes before slicing and serving. This allows the pie to set properly for clean slices. Enjoy warm or at room temperature.