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Heat the olive oil in a large cast iron skillet or heavy-bottomed pan over medium-low heat. Add the thinly sliced onions, salt, and granulated sugar (if using). Cook, stirring occasionally, for 20 to 25 minutes, or until the onions are deeply golden brown, very tender, and caramelized. Remove the caramelized onions from the skillet and set aside.
While the onions are caramelizing or cooling, gently divide the ground beef into 4 equal portions (approximately 6 ounces each). Loosely form each portion into a ball; avoid overworking or compressing the meat. Season all sides of the beef balls generously with kosher salt and freshly ground black pepper.
Wipe the skillet clean if necessary, or use a separate skillet. Brush the cut sides of the burger buns with the melted unsalted butter. Place the buns cut-side down in the hot skillet over medium heat and toast for 1 to 2 minutes, until golden brown and lightly crispy. Remove the toasted buns and set aside.
Increase the skillet heat to medium-high until it is very hot and just beginning to smoke. Place two beef balls in the hot skillet, ensuring there is space between them. Immediately use a sturdy metal spatula (or a burger press) to firmly smash each beef ball flat into a thin patty, about 1/4 inch thick and slightly wider than the burger bun.
Cook the smashed patties undisturbed for 2 to 3 minutes, until the edges are crispy and deeply browned. Flip the patties. Immediately place one slice of American cheese on top of each patty. Continue to cook for another 1 to 2 minutes, or until the cheese is fully melted and the burger is cooked through to your desired doneness. Transfer the cooked cheeseburger patties to a plate. Repeat steps 4 and 5 with the remaining two beef balls and cheese slices.
Assemble the smash burgers: Place a cheeseburger patty on the bottom half of each toasted bun. Top generously with the prepared caramelized onions. Add dill pickle chips if desired. Place the top bun on each burger and serve immediately.

Heat the olive oil in a large cast iron skillet or heavy-bottomed pan over medium-low heat. Add the thinly sliced onions, salt, and granulated sugar (if using). Cook, stirring occasionally, for 20 to 25 minutes, or until the onions are deeply golden brown, very tender, and caramelized. Remove the caramelized onions from the skillet and set aside.
While the onions are caramelizing or cooling, gently divide the ground beef into 4 equal portions (approximately 6 ounces each). Loosely form each portion into a ball; avoid overworking or compressing the meat. Season all sides of the beef balls generously with kosher salt and freshly ground black pepper.
Wipe the skillet clean if necessary, or use a separate skillet. Brush the cut sides of the burger buns with the melted unsalted butter. Place the buns cut-side down in the hot skillet over medium heat and toast for 1 to 2 minutes, until golden brown and lightly crispy. Remove the toasted buns and set aside.
Increase the skillet heat to medium-high until it is very hot and just beginning to smoke. Place two beef balls in the hot skillet, ensuring there is space between them. Immediately use a sturdy metal spatula (or a burger press) to firmly smash each beef ball flat into a thin patty, about 1/4 inch thick and slightly wider than the burger bun.
Cook the smashed patties undisturbed for 2 to 3 minutes, until the edges are crispy and deeply browned. Flip the patties. Immediately place one slice of American cheese on top of each patty. Continue to cook for another 1 to 2 minutes, or until the cheese is fully melted and the burger is cooked through to your desired doneness. Transfer the cooked cheeseburger patties to a plate. Repeat steps 4 and 5 with the remaining two beef balls and cheese slices.
Assemble the smash burgers: Place a cheeseburger patty on the bottom half of each toasted bun. Top generously with the prepared caramelized onions. Add dill pickle chips if desired. Place the top bun on each burger and serve immediately.