Line a large jelly roll pan with parchment paper for easy cleanup.
In a large, heavy-bottomed pan with a lid, heat the oil over medium heat. Add 2 popcorn kernels and cover.
Once the test kernels pop, add the rest of the popcorn kernels. Shake the pot to distribute them evenly and cook, slightly ajar, until the popping slows down.
Transfer the popped popcorn to the prepared pan, season with sea salt, and remove any unpopped kernels.
Place candy canes in a plastic bag, cover with a towel, and crush using a rolling pin or hammer.
Use a double boiler or microwave to melt the chocolate chips until smooth, stirring frequently.
Drizzle melted chocolate over popcorn, sprinkle with crushed candy canes and optional salt, then chill in the refrigerator until set.