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Ah, fall. I know I'm not alone in choosing this season as my favorite: every single year, when it rolls around, I'm ecstatic for the return to crisp air, scarves and jackets, hot coffee, and, of course, soup. I eat a lot of chilled soups during the summer, but I won't touch hot ones with a ten-foot pole: swampy New York weather provides me with quite enough heat and steaminess, thank you very much.
In appropriate weather, I do love hot soup, and I find myself reaching for my favorite deep, heavy-bottomed soup pot as soon as it turns cool at the beginning of autumn. And tomato soup is one of my very favorites to make. Now, I wasn't one of those kids who grew up on the stuff, as I absolutely hated tomatoes. Insane, right? It was a textural thing: I couldn't get past those squishy, jelly-like seeds inside. So, logically (in kid world, at least), my hatred extended to tomato anything: sauce, salad, and, of course, soup.
As a result of my no-tomato-soup policy, I missed out on what I now gather is a major part of the childhood culinary experience: tomato soup served with a buttery, oozy grilled cheese alongside, to be eaten dipped into the soup. Since growing up and first accepting and eventually adoring anything involving tomatoes, I've prepared this soup-and-sandwich combo for myself many a time. And it's from this classic pairing that I got the inspiration for the recipe I'm sharing today, a warming, filling soup made with roasted tomatoes and served with crusty, cheesy cheddar croutons on top.
The soup itself is somewhat unusual, but couldn't be simpler: canned tomatoes get drained of their liquid, spread out on a roasting pan, and baked with brown sugar until they're bubbly, browned, and intensified in flavor. I learned the sugar/roasting trick years ago at a now-defunct catering company, and I've kept it in my roster ever since: it's perfect for smoothing out the sometimes over-the-top acidity that tomatoes can have. Rather than making the soup taste sweet, the brown sugar simply vanishes into the background, making the soup's flavor a lot more full and rounded. The roasted tomatoes then get cooked in their reserved liquid plus a little water, blended smooth with a touch of half and half, and topped with the cheesy nuggets of crisped bread. I suspect that had my mom served this soup to me as a kid, my bias against tomatoes would have vanished in an instant.