Preheat oven to 425°F (220°C).

Remove papery outer skin from garlic bulb, but do not peel or separate the cloves.

Cut off top of garlic bulb, exposing individual cloves.

Brush cut cloves with 1 teaspoon of olive oil.

Wrap garlic bulb in foil.

Bake until cloves are soft, about 30-35 minutes.

Unwrap and cool slightly.

Squeeze garlic from skins; mash with a fork.

In a large dry skillet over medium-high heat, toast ancho and chipotle chilies on both sides until puffy, about 3-6 minutes.

Cool toasted chilies.

Remove stems and seeds from the chilies.

Coarsely chop the chilies.

Place chopped chilies in a small bowl and cover with dark beer.

Let chilies stand in beer until softened, about 30 minutes.

In the same skillet, heat 1 tablespoon of olive oil over medium-high heat.

Brown beef stew meat in batches, adding additional oil if needed.

Transfer browned beef to a 6-qt slow cooker.

In the same skillet, heat 2 teaspoons of olive oil over medium heat.

Add chopped onions to the skillet and cook until tender.

Add cooked onions to the slow cooker with the beef.

Stir in rinsed and drained kidney beans, diced tomatoes (undrained), tomato sauce, Worcestershire sauce, chili powder, pepper, salt, mashed garlic, and the softened dried chilies mixture into the slow cooker.

Cover and cook on low until meat is tender, about 7-9 hours.

Serve the Spicy Cowboy Chili, optionally topped with shredded cheddar cheese.