Place tomatoes and whole, skin-on garlic cloves on a baking sheet. Sprinkle with olive oil and toss to coat. Roast in a preheated 450 F oven for 25-30 minutes. Remove from oven and cool completely. Remove paper skin from garlic cloves. Place tomatoes, peeled garlic, cream cheese, sour cream, and salt and pepper into the work bowl of a food processor fitted with metal chopping blade. Process until smooth. Garnish and serve at room temperature. Can be made up to 2 days in advance. Refrigerate leftovers.