Tiny Taco Salads

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Vegetable oil, for the skillet

8 ounces lean ground beef

Kosher salt and freshly ground black pepper

1/2 cup shredded lettuce

24 tortilla chip cups, such as Tostitos Scoops

1/2 cup shredded Monterey Jack cheese

1/4 cup salsa 

1/4 cup sour cream 

1/4 cup guacamole 

12 cherry tomatoes, sliced in half 

Fresh cilantro leaves, for garnish