To prepare the toppings: Heat a big pan over medium heat and line up the bacon slices. Cook until golden and crispy. Drain.
Heat the broiler. Line a baking sheet with parchment paper. Brush both sides of the pineapple with butter and lightly sprinkle with brown sugar. Place on baking sheet and broil until caramelized, about 5 minutes.
Shape beef into 4 wide 1-inch thick patties. Heat the canola oil in a pan on medium-high. Sear patties for 2 minutes on each side, until they develop a nice crust. Reduce the heat to medium-low and cook for an additional 3 minutes per side. Top each patty with a slice of mozzarella cheese and melt.