Preheat the oven to 300 F, remove the excess papery skins off of the heads of garlic (keep the heads intact), and prepare 2 pieces of aluminum foil big enough to wrap each head. Keeping the garlic head intact, cut the top (about 1/4") off of each garlic head to just expose the cloves of garlic. Place each head of garlic on the aluminum foil, drizzle each with olive oil, sprinkle with salt and wrap the garlic tightly in the aluminium foil. Bake for 1 hour, seam-side up.
Once the garlic is done, remove from oven and set aside. Turn the heat up to 400 F and place the bacon on a parchment lined baking sheet. Cook for 15-20 minutes, until crispy. Transfer the bacon to a plate lined with paper towels to drain. Cool and roughly chop the bacon.
Combine the lemon juice, Dijon mustard, anchovy fillets, and a ¼ cup of grated parmesan cheese in a food processor or blender. Squeeze all of the roasted garlic out of the skins into the food processor or blender and blend to combine. With the processor or blender running, slowly drizzle in the olive oil. Season with the sugar and salt and pepper to taste.
When ready to eat, place the chopped kale and romaine into a large bowl and toss in the bacon and croutons. Toss with the dressing, garnish with extra parmesan and serve!