Process the crushed tomatoes in a blender or food processor, one can at a time, until smooth. Set aside.

Add crushed tomatoes and vegetable stock to a 6 quart or larger saucepan. Whisk to combine, then bring to a boil over high heat, then reduce heat to medium and simmer for 10 minutes.

Meanwhile, in the same blender or food processor you used before, add the stewed tomatoes and cream cheese. Cover and process until smooth.

Gradually stir the cream cheese mixture, oregano, basil, garlic and sugar into the pan with the tomatoes and stock.

Place half and half and cream into a large, heat proof bowl. Temper the half and half and whipping cream by slowly whisking about a cup of the hot tomato mixture into the cold mixture (this will prevent the cream from curdling). Whisk the tempered mixture back into the saucepan with the rest of the soup and let it warm through for a couple of minutes, but don't let it boil.

Garnish with a grilled cheese sandwich (remove the crust prior to grilling, if desired) that has been cut into small, crouton-sized squares, and sprinkle with a bit of freshly grated Parmesan cheese.