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Preheat oven to 425°F.
Place Brussels sprouts on a rimmed baking sheet and drizzle with olive oil. Season with salt and pepper and toss to coat.
Add bacon to sheet pan and toss once more, making sure that sprouts are in a single layer and spaced out.
Roast for 12 minutes, then stir to move sprouts around, making an attempt to flip them to the other side. Bake until brown and crisp, 10-12 minutes more.
Remove from oven and toss with balsamic vinegar. Season with a bit more salt, serve, and enjoy!