Tomato soup is one of those things that I love, but only if it's made well. Not too runny, not too creamy, not too sweet, not too sour. All of the other ingredients should complement the tomato and bring out the flavor, not cover it up. The simplicity of this soup is what makes it so great. It only has five ingredients (not counting salt, is that cheating?).
I found these gorgeous on-the-vine tomatoes from Whole Foods the other day and just couldn't resist picking up a few clusters. Last year I tried growing my own heirloom tomatoes. They were beautiful, but before I harvested any they all contracted some sort of nasty bacterial infection, aka the dreaded black rings of death. My neighbors however, successfully plucked a few and said they were the most delicious tomatoes they had ever eaten. Believe you me, if they hadn't all died a terrible death, they would have found their way into this very soup.
This soup takes a long, long time to make, but it's mostly passive time. I recommend getting started around noon if you plan on having it for dinner. Slow roasting the tomatoes is the secret to making a super delicious tomato soup without a whole bunch of unnecessary flavor enhancers. Trust me, it's worth it.
Depending on if your oven runs cool or hot, adjust the roasting time accordingly. I also recommend using an oven thermometer.
You could substitute half & half for the heavy cream if you're trying to be healthier. I don't recommend using milk as the heat and acidity from tomatoes could (read: will probably) make it curdle.
4 lbs of the freshest tomatoes you can buy, quartered
5 cloves of garlic, unpeeled, smashed
1/4 cup olive oil
2 tbsp granulated sugar
1 tsp salt
1/2 cup heavy cream
Place tomatoes and garlic in a large baking pan and coat with olive oil. Place in oven, no need to preheat, and roast at 250 degrees F for 5 to 6 hours. The tomato juices should have reduced down by a third to a half.
Transfer entire contents of the baking pan to a mixing bowl and blend with an immersion blender (or transfer to regular a blender). Strain through a fine mesh sieve into a dutch oven and bring to a simmer. Add sugar and salt. If the soup is too thin, simmer for 10 to 20 minutes until it thickens a bit. If the soup is too thick, add some water, stir well, and simmer for 3 to 4 minutes until well incorporated.
Turn off heat and stir in cream. Serve immediately (I highly recommend alongside a grilled cheese).