Heat olive oil in a 12-inch heavy-bottomed skillet over medium-high heat.
Add ground beef and diced onion to the skillet; cook until beef is fully browned and onion is translucent, approximately 7-8 minutes. Drain excess rendered fat.
Add chopped bell peppers and minced garlic to the skillet; sauté for 3 minutes until peppers are slightly softened.
Stir in the diced tomatoes, uncooked rice, beef broth, salt, pepper, paprika, and oregano until well combined.
Bring the mixture to a simmer, then reduce heat to low and cover the skillet with a tight-fitting lid.
Cook for 18-20 minutes without lifting the lid, until the rice is tender and the liquid is completely absorbed.
Remove skillet from heat, sprinkle shredded cheddar cheese evenly over the surface, and cover for 2 minutes to allow the cheese to melt.
Fluff the mixture gently with a fork and serve immediately.