This is the current version of the classic tomato pie my family makes (Lila's Tomato Pie, also on this site). The fresh tomato pie, although delicious, can have an element of wateriness despite draining and I wanted to concentrate the tomato flavor so I started roasting the tomatoes before they go into the pie shell. The result was a sweeter, stronger and more chewy filling. I also decided just to roast the garlic along with the tomatoes so the garlic flavor is rounder and sweeter, too. The topping has always been a bone of contention in the family and I've done lots of variations on the original cheddar/mayo combination like sour cream and goat cheese, or shaved Parmesan and mayo or sour cream. But then I recently remembered a truly toothsome gratin from Deborah Madison's Vegetarian Suppers that is topped with a saffron custard. I've pretty much stuck to her custard recipe except that I've exchanged the saffron for fresh basil so that you bite through a pillowy layer of basil and cheese soufflé to get to the sweet, tart tomatoes. Great is the family's delight when this is in the oven! If any is left, it is delicious the next day, but rather homely looking. —JadeTree
For the roasted tomato filling:
Recipe single pie crust
Ripe yet firm tomatoes, thickly sliced
Plump cloves of garlic
Kosher salt and pepper
The basil custard topping:
Ricotta (fresh would be amazing!)
Finely chiffonaded fresh basil from a solid handful
Preheat oven to 425. Settle racks in the top and bottom thirds of the oven.
On two baking sheets, spread out a layer of parchment and then pour 2 tablespoons of olive oil (3 if you like things extra juicy) on each sheet. Chop the garlic, without attention to nicety, and sprinkle three cloves worth on each sheet and smear the oil and garlic over the entire base of the pans.
After thickly slicing the tomatoes, about 1 inch thick, dredge each slice in the garlic oil mixture once and then flip over so that both sides are coated. Fill both baking sheets with tomato slices and give both pans a lusty casting of kosher salt.
Note: the end piece of the tomatoes with all of the skin on them are fine here. Roast them skin side up and when they are done you can just skim off the tough skin, like unfashionable hats, and discard them so that your pie will be more silky. I don't bother with the skin on the sliced pieces.
Slide each pan onto a rack and roast for 20 minutes. Then switch the pans from top to bottom as though you were baking cookies and roast a final 20 minutes (40 minutes total). The tomatoes should get very soft and wrinkly and the juices may get kind of dark on the parchment. You don't want them to be desiccated, though.
Set aside pans of tomatoes on cooling racks. Lower oven to 375.
Roll out pie crust and fit into a 9-inch pie plate. (If you want to do a deep dish version of this pie then you will need to add a few more tomatoes.) Cover with parchment and weight with whatever and bake 10 minutes. The crust will dry and start to color a bit. Remove and set near the tomatoes. I fill hot crusts all the time so it won't matter if you start right away or wait for a bit.
Heap the tomatoes into the crust making sure the garlic comes along. There should be a good inch or so between the top of the tomatoes and the top of the crust.
Prepare the topping. Whisk together the eggs, ricotta and milk with 1/2 teaspoon of salt. Add the finely sliced basil and stir to incorporate. Crumble in the goat cheese and Parmesan and mix well. Pour over the top of the tomatoes. Depending on how full your crust ended up, you may have extra. Alas! Don't flood the crusts on the edges.