In a large pot, place the olive oil and butter over medium-low heat. Once the butter is melted, add the onions, sprinkle with a pinch of salt, and cook, stirring occasionally, until softened and deeply golden, around 45 minutes. Adjust the heat as needed between medium low and low to keep the onions from burning before they get a chance to caramelize.
Stir in the garlic and cook just until fragrant, 30 seconds to 1 minute.
Increase heat to medium-high. Pour in the whiskey and stir, scraping up the browned bits from the bottom of the pan. Add the Guinness and simmer until reduced by half.
Pour in the beef broth followed by the Worcestershire sauce, thyme, and bay leaf. Season with salt and pepper and bring to a boil.
Reduce to a simmer and cook for another 30 minutes, stirring occasionally, to allow the flavors to blend. Remove the bay leaf and thyme stems. Adjust seasonings to taste.
While the soup is cooking, slice the baguette into 1/2 inch (1.25 centimeters) thick slices and toast under a broiler until golden.
Divide the soup among broiler safe bowls. Top each with a toasted slice or two of baguette. Cover with a large handful of shredded Irish cheddar cheese. Place bowls on rimmed baking sheet and broil until the cheese is melted and starting to brown and bubble.
If desired, top with fresh parsley or chives and serve immediately with the remaining slices of baguette for dipping.