Scrub the russet potatoes clean and prick them with a fork a few times. Rub each potato with olive oil, and season with salt and pepper. Place them directly on the oven rack or a baking sheet and bake for 45-60 minutes, until the potatoes are tender when pierced with a fork.
While the potatoes are baking, heat your chili in a saucepan over medium heat, stirring occasionally until warm. If using store-bought chili, feel free to add any extra spices or seasonings to customize the flavor.
Once the potatoes are baked, remove them from the oven and let them cool slightly. Cut each potato in half lengthwise and scoop out some of the flesh, leaving a small border around the edges to form a boat shape.
Place the scooped-out potato flesh in a bowl and mash it with a fork. Add salt, pepper, and smoked paprika (if using), then set aside.
Fill each potato boat with a generous amount of chili, then top with the mashed potato mixture, pressing it down gently to compact it. Sprinkle shredded cheddar cheese over the top of each boat.
Return the potato boats to the oven and bake for an additional 10-15 minutes, or until the cheese is melted and bubbly.
Remove from the oven and top with a dollop of sour cream, chopped green onions, and crispy bacon bits, if desired. Garnish with fresh cilantro.
