Preheat oven to 400°F and toss cherry tomatoes with 1 tablespoon olive oil, garlic, salt, and red pepper flakes on a baking sheet.
Roast tomatoes for 20-25 minutes until they're blistered and starting to collapse, then remove from oven and set aside.
While tomatoes roast, add mozzarella pieces and heavy cream to a food processor and blend for 1-2 minutes until smooth and whipped.
Transfer whipped mozzarella to a serving bowl or shallow dish, spreading it into an even layer.
Top the whipped mozzarella with the roasted tomatoes and their juices, drizzle with remaining olive oil, and garnish with fresh basil.
Serve warm or at room temperature with crusty bread or crackers for dipping.