Pre-heat oven to 400°F.
Cut the Brussels sprouts into quarters. Toss liberally in olive oil and salt. Roast until crispy, soft, and dark brown in spots, about 30 minutes.
Toss kale lightly in olive oil and bake slowly in a single layer on a sheet tray in a 300°F oven until crispy, about 30 minutes. Resist the urge to pile on kale as it can result in a soggy "chip."
Set Brussels sprouts and kale aside to cool.
To make dressing: Blend garlic, anchovy, and half and half together in blender until smooth. Add vinegar, Dijon, lemon juice, and lemon zest. Add yolk. While blender is on low, slowly add the olive oil. To finish add Tabasco, Worcestershire, Parmesan, and cracked pepper.
In a large bowl, place romaine, roasted Brussels sprouts, crispy kale, shredded Parmesan, and croutons and toss with dressing. Garnish with shaved Parmesan. Finish with a drizzle of olive oil to really drive the flavor home.