Place a pot of water on to boil and lay out a sheet pan and a large bowl of ice water. Lay out a second sheet pan with parchment paper for baking.
Pull off stem and make an X on the opposite end of each tomato with a sharp knife.
Work in batches of 8-10 tomatoes at a time and drop them into the hot water. After about a minute, the skin will start to peel. Remove them with a spider or strainer and plunge into the ice bath. Then remove from the ice water onto the sheet pan and peel off and discard skins. Repeat for all of the tomatoes.
On a cutting board, split each tomato the long way for plum and horizontally for regular round tomatoes.
Scoop out the seeds and pull off the stem. Lay the tomato half cut side up on the prepared parchment lined sheet pan. (For the round tomatoes, squeeze over a bowl and reach a finger up into each seed cavity to release the seeds.) Leave the core in but remove after baking.
Preheat the oven to 275 degrees F.
Once all of the tomatoes are skinned and seeded and are on the parchment lined sheet pan, drizzle the tops with the olive oil and sprinkle the salt, pepper and pepper flakes over the tomatoes.
Bake for between two and three hours depending on the water content of the tomatoes. High water content tomatoes will take the full three hours. When you check them, they should just barely be starting to dry out but still be moist and supple. Do not over cook them otherwise they will dry out and stick to the pan. If you see a lot of water collecting on the pan, pour that off.
Remove from the oven and cool.
Place in a bowl and add fresh basil and toss. Can be served hot or cold with any meat or fish.
Last Step! Please leave a review and rating letting us know how you liked this recipe! This helps our business thrive & continue providing free recipes.