Combine 1 teaspoon oil, tomatoes, and garlic on a baking sheet. Bake at 400° for 20 minutes. Remove skins from tomatoes; discard skins. Squeeze garlic to extract pulp; discard garlic skins. Combine tomatoes, garlic pulp, basil, salt, and pepper in a mini food processor; pulse 10 times.
Combine mayonnaise and cream cheese in a medium bowl. Add cheddar, stirring well to combine (mixture will be very thick). Spread one-fourth of cheese mixture (about 2 tablespoons) over each of 4 bread slices; top each with about 1 1/2 tablespoons tomato mixture and 1 bread slice. Lightly coat outsides of sandwiches with cooking spray.
Heat a large skillet over medium heat. Add 1 teaspoon oil; swirl to coat. Place sandwiches in pan; cook 3 minutes or until lightly browned (do not flip). Remove sandwiches from pan. Add remaining 1 teaspoon oil; swirl to coat. Turn sandwiches over, and add to pan; cook 3 minutes or until lightly browned and cheese melts. Cut in half; serve immediately.
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Lovely flavor, though I think next time I'd combine the tomato mixture with regular shredded cheese and not bother with the mayo/cream cheese mixture. It made the sandwich more tangy, less cheesy, and I want my grilled cheese CHEESY. CL used this method (shredded cheese + mayo + cream cheese) in another recent grilled cheese recipe, and it's just not for me. But love the roasted tomatoes!
These are really delicious and definitely achieve the claim of getting grilled cheese and tomato soup flavor in one sandwich. I used Trader Joe's sourdough whole wheat boule and it was perfect for this. I'm not sure what lrose17 is thinking here--I thought this was a perfect and easy recipe; perhaps she's comparing it to making plain grilled cheese? Hands-on time was maybe 15 minutes. You can roast the tomatoes the night before to save time.
These were really good, but a lot of work. They're definitely not something you whip up on short notice. I can't claim that I measured every ingredient very carefully, but this only made three sandwiches for us.
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