Preheat oven to 250F, with rack on lower position.In a very large heavy pot, add 5 TB oil and 3 corn kernels. Heat on medium-high with lid on and start to listen. Once the first kernel pops, carefully add the 1 cup corn kernels. Shake pan to coat kernels with oil. Place lid slightly ajar to allow steam to escape during popping. Shake pot occasionally during popping. Once the popping slows to 2-3 seconds in between, immediately remove from heat and transfer popped corn into a large roasting pan.Place roaster in oven to keep popcorn warm.In a heavy saucepan, add brown sugar, corn syrup, salt, and butter. Bring to boil over medium heat, stirring. Boil 5 minutes, stirring/scraping constantly. Remove from heat and gently add the baking soda and vanilla. Mixture will turn foamy as you stir. Stir until mixture is thickened.Pour mixture over warm popcorn and stir to coat as much as you can, with popcorn in an even layer. Bake 1 hour, stirring every 15 minutes to coat.Transfer caramel corn to a lined baking sheet to cool. Separate the pieces as much as you can and let cool completely. Serve upon cooling or keep in airtight container.Note: If you're making double the amount, do it in separate batches. I've found that if the roaster is too full with popcorn, it won't crisp up as nicely.