In large pot over medium heat, heat the oil and place 3 kernels in the center of the pot. Wait for the 3 kernels to pop as it's a signal that your oil is hot enough to start.
Turn up the heat slightly more, toss in remaining corn kernels, cover the pot, and shake the pot continuously over the heat.
In a separate small pan on medium-low, melt the butter.
Once the corn kernels have slowed down their popping (listen for single pops, typically 5 to 7 minutes in), remove the popcorn from the heat and pour it into a large serving bowl.
Drizzle the butter over the popcorn and add in the Old Bay, the salt, and the pepper. Toss the popcorn until it's evenly covered with the butter and spices.