Step 1

Preheat the oven to 450°F.

Step 2

Line a baking sheet with parchment paper.

Step 3

Slice the heads of garlic in half horizontally and place them on a large piece of foil. Add the shallots, drizzle with olive oil, season with salt, and wrap everything in the foil.

Step 4

Brush the cut side of the eggplant lightly with olive oil.

Step 5

Place the eggplant halves cut-side down on the prepared baking sheet.

Step 6

Optionally, brush a little oil on the skin as well.

Step 7

Roast at 450°F until soft and caramelized, about 25-35 minutes depending on size.

Step 8

Remove the eggplant, garlic, and shallots from the oven and let them cool.

Step 9

Peel the eggplant and squeeze the garlic out of its skin.

Step 10

In a food processor, combine the canned tomatoes, roasted eggplant, shallots, and garlic. Season with salt, black pepper, and 1 teaspoon of chili flakes. Add the basil and process until everything is combined.

Step 11

Cook the pasta in a pot of boiling salted water according to the package instructions (al dente), then drain, reserving a cup of the cooking water.

Step 12

Heat ¼ cup of olive oil in a pan over medium-high heat. Add the tomato paste and sizzle for one minute.

Step 13

Add the tomato-eggplant mixture to the pan, and cook for 2-3 minutes, allowing the liquids to evaporate. Then add the heavy cream and cook for an additional 3-4 minutes. Adjust salt and black pepper to taste.

Step 14

Add the al dente penne, Parmesan, and reserved pasta water. Mix over medium heat for about 3 minutes, or until you achieve a smooth and creamy texture and the pasta is fully cooked.

Step 15

Serve topped with grated Parmesan cheese and additional chili flakes if you prefer extra heat.