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Cut tomatoes in half; squeeze gently over the sink to get rid of excess water and seeds; dump in a baking pan; dribble with olive oil and scatter a whole bunch of whole garlic cloves in and roast, at about 400F until the tomatoes are slightly charred in places and fully baked.
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2
If you want, you can just pick off the tomato skins and discard.
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I usually just puree the lot.
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I will often stir some fresh oregano and/or basil in about halfway through this process.
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When done, puree this roasted tomato mess and add some half and half (how much you want to use depends entirely on you - sometimes you want a pure tomato flavour, other times, it may be too much of a good thing and you may want a creamier, less-pronounced taste).
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Season to taste, using LOTS of freshly-cracked pepper.
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The most awesome roasted tomato soup ever.
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Note: The tomato-mess, without the addition of the half and half, is a good base for many recipes calling for tomato sauce.
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Or add the cream and use to toss with freshly-cooked pasta.
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Second Note: If you like a thinner soup, use hot broth or even water to bring it to the desired consistency.
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Check seasoning.