Heat the olive oil in a large skillet over medium heat. Add the diced onion and green bell pepper and sauté for about 3 minutes until they begin to soften. Add the ground beef and minced garlic, breaking up the meat as it cooks until there is no pink left.
Stir in the chili powder, salt, sugar (if using), and pepper. Mix in the uncooked rice, diced tomatoes with juice, water, and Worcestershire sauce. Bring the mixture to a simmer, then cover the skillet. Let it cook for about 20 minutes, stirring once or twice, until the rice is tender. Add a little more water if the mixture seems dry.
Fluff the rice with a fork. If desired, sprinkle the shredded cheddar cheese on top and allow it to melt before serving. Garnish with cilantro.