Preheat the oven to 425°F and place a large sheet pan inside while it heats. A hot pan makes crispy brussels sprouts.
Prep the brussel sprouts (5 min): Trim the ends of the brussel sprouts and halve lengthwise (quarter if they’re large). Toss in a bowl with olive oil, salt and pepper.
2 lbs brussels sprouts, 2 Tablespoons olive oil, 1 teaspoon kosher salt, 1/4 teaspoon fresh cracked black pepper
Roast (30-35 min): Carefully remove the hot sheet pan from the oven and arrange the brussels sprouts cut-side-down in a single layer. Roast without stirring until they’re deeply golden and slightly charred in places, 30-35 minutes.
Make the maple bacon glaze (8-10 min): While they’re roasting, cook the bacon pieces in a medium skillet over medium-high heat, until brown and crispy, 3-4 minutes. Transfer the bacon to a paper towel and discard the bacon grease, leaving the brown bits in the pan. Add the balsamic vinegar and bourbon and stir over medium heat to scrape the brown bits from the pan. Stir in the maple syrup and bring to a gentle boil over medium heat. Turn the heat down to low and simmer, stirring frequently, until slightly thickened, 2-3 minutes. Add the bacon bits back in and stir to coat.
4 slices bacon, 3 Tablespoons balsamic vinegar, 1-2 ounces bourbon, 1/3 cup maple syrup
Toss and serve (5 min): When the brussels sprouts are done, turn the oven off, remove the brussels sprouts and pour the maple bacon mixture on top. Toss to coat evenly then place them back in the turned-off oven for 2-3 minutes (or until ready to serve) to let the maple soak in. Toss with additional toppings and serve hot and crispy right away.