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Roasted Tomato Soup w/ Grilled Cheese Garnish ...for PFB challenge #4

I'm gonna let you in on a little secret.  When I was a little girl, I did not like Tomato Soup.  Heck, I didn't even like it when I was a teenager or even as a young adult.  Really.  That thick red liquid...plopped from a red and white can...and then combined with water.  Eeewwww.  Can you blame me?  Oh, and I hear that question playing on the tip of your tongue...What, pray tell, did you dip your grilled cheese sandwiches in then? {Pshhhh...  Pfffft.... Eye-roll...} Something waaaay better than tomato soup.  Ketchup, of course.

Those of you who know me even a little probably know that soup in general is one of my favorite meals.  And if you didn't know it before, then you know it now!  Anytime of the year....brothy, stewy, chunky, creamy, simple, complex...I loves me some soup.  Yup, I'm that girl in the dog days of summer slurpin' up a big bowl of spicy, chile-laden soup to ward off the heat.   Don't believe me?  Try it some time.  Nothin' like getting the sweat rolling from your forehead to start the cooling process.  I digress. 

Back to the topic at dislike of good 'ol tomato soup.  Or rather, my former dislike.  Because upon my discovery of homemade tomato soup, that red goo-in-a-can that caused shivers down my spine, was instantly forgotten.  Can you believe it's only been about ten years since that discovery?  I was mid-twenties and somewhere in the throws of culinary school -- knee-deep in soups, stocks, and sauces.  Chef suggested I char some tomatoes and garlic on the grill before throwing them into my soup pot.  This brought out a deep, rich, earthy sweetness from both the tomatoes and the garlic...I was hooked.  To this day, I cannot make tomato soup without first grilling or roasting the tomatoes and garlic.  And YES, there's ALWAYS garlic.  Plus,  now I can  dip my grilled cheese in my tomato soup.  But also my ketchup... 
The brilliant thing about first roasting or grilling your tomatoes is that you can use tomatoes even out of season and get great results...coaxing that hidden flavor that wishes it could flaunt itself like a summer tomato.  But that doesn't mean you have to make it out of season.  No sir!  Use all red tomatoes for the deepest color...or just use what you've got. 

While tomato season is pretty much over here in northwestern Indiana, our plants have basically refused to recognize that fact.  So, I grabbed a basket and took full advantage of what was probably my last big tomato harvest.  I used a combination of what we grow...and what the neighbors grow.  They've given me full reign because they're busy and their garden's gotten away from them this year.  I gladly oblige.  So I've got Sunrays, Tigerellas, Green Zebras, Romas, some varietals of grape & cherry tomatoes. This is also a good opportunity to use up end of the season herbs.  My basil was looking pretty rough, so I cut it all the way back and added it to the soup, as well.  It's okay if your herbs are looking beat up and little bruised...they get blended in.  Also, my affinity for garlic means I tend to use a lot...if you're not as down with it as I am, use the lesser amount.
Roasted Tomato Soup
w/ Grilled Cheese garnish
from the kitchen of girlichef
yield: ~2½ qts.

~6 lb. tomatoes, any variety you wish
huge handful of basil
1-2 heads of garlic, peeled
olive oil
sea salt
freshly ground black pepper
1 qt. chicken stock/veg stock/water (+ a little more, as needed)

Begin by weighing out your tomatoes and washing any dirt from them.
Quarter the tomatoes...or if you're using smaller ones, simply halve them.
Pull all of the basil leaves from their stems.  Rinse off any dirt.  Roughly chop it.
Place the tomatoes and basil in a bowl (or two) and drizzle with olive oil, salt and pepper.  Toss well with your hands.  You want just enough olive oil to lightly coat the tomatoes.  Oh, and don't forget to add in your garlic cloves.  Like I did.  Because I was so smitten by the pretty colors and the glorious weather of this Indian Summer day... If you do, just toss in the bowl with the oil and herbs that are still stuck to the sides.  Then lay out everything on some lined baking sheets.  Place them in an oven preheated to 325° F. for ~1 hour, or until they are soft and a bit golden in some spots.
Transfer to a large dutch oven (or soup pot), using the liner underneath to lift and pour...this way you get any juices that accumulated in the pot, as well.  Add the liquid and bring to a boil.  Reduce heat to a simmer and let cook for 20-25 minutes.  Purée with an immersion blender (or alternately in a jar blender) until smooth.  Strain the soup.
Or don't strain it.  But fair warning...this is what will get stuck between your teeth if you don't...
Pour the strained liquid back into the (cleaned) pot and bring it back to a boil. If it seems too thick for your liking at this point, simply add in a bit more liquid...if it seems too thin, simmer it for a while to reduce it. Turn off heat.  Taste and adjust seasoning if necessary.
While you're reheating your soup...make yourself a grilled cheese sandwich.  OR!!!  Better yet...add a little whimsy by making mini-grilled cheese garnish for your tomato soup!  You can use any type of bread and cheese you desire.  I tend to crave the American "cheese" on white bread variety that I grew up with, for this particular application.  But again, if you know me even a know I'm a total cheeseslut and a breadwhore to take it how I can get it... 

Butter one side of each slice of bread (I go one sammich per person).  Lay a slice or two of cheese on an unbuttered side of the bread.  If I'm making a bunch, I like to stack them buttered-sides together in a row.  Lay one slice of bread, butter side down on a hot comal/skillet and cover with the other slice of bread, butter side up.  Flip when crisp and golden on the bottom and repeat.  Use a small "cutter" in any shape  you desire...I use an apple cut minis from the sandwich.  Set them aside to use as garnish.  Don't throw away those holey sammies, though!!  Those are just bonus for eating on the side.  Cuz lets face it...those adorable teeny-tiny circles would never be enough!
Now it's time to eat!  Ladle the hot soup into bowls...and serve a little side dish with the grilled cheese garnish on the side for people to sprinkle on as they like...all at once...bite by bite...let 'em be in charge of their own destiny!
I like to call that a little bowl of perfection.  But, that's just me.