Line a rimmed baking sheet with aluminum foil and place a broiler safe rack inside.
Arrange halved tomatoes evenly on the rack, cut side up on. Brush each tomato half with olive oil using a silicone or pastry brush; season with salt and pepper.
Place the baking sheet on the highest oven rack and bake broil 15 to 20 minutes. Check tomatoes at the 10-minute mark to determine the remaining time needed. You don’t want to completely burn the tomatoes, but leave them slightly charred.
When the tomatoes are done to your liking, remove the baking sheet and set aside until the tomatoes are cool enough to handle.
Peel the skin off each tomato half (it should come off easily - recipe note #2). Chop tomatoes (if desired) and use immediately or transfer to an airtight container and refrigerate for up to 5 days or freeze for up to 6 months.
Notes
Yield is ~2 1/2 cups
Alternatively, you can puree the tomatoes with the skin, using an immersion blender or standard blender.