Preheat your oven to 350°F (175°C). Grease and flour a baking pan. In a large mixing bowl, cream together the softened unsalted butter and caster sugar until light and fluffy. Add in the eggs, cooking oil, cocoa powder, red food coloring, vanilla extract, and vinegar, mixing until well combined.
In another bowl, whisk together the all-purpose flour, baking soda, and salt. Gradually add the dry mixture to the wet ingredients, alternating with the buttermilk, starting and ending with the flour mixture. Mix until just combined. Pour the batter into the prepared baking pan and smooth the top.
Bake in the preheated oven for 25-30 minutes, or until a toothpick inserted in the center comes out clean. Let the cake cool in the pan for 10 minutes before transferring it to a wire rack to cool completely.
While the cake is cooling, prepare the frosting. In a mixing bowl, beat the softened unsalted butter until creamy. Gradually add the powdered sugar, vanilla extract, heavy whipping cream, and a pinch of salt. Beat until smooth and fluffy.
Once the cake has cooled, crumble it into a large mixing bowl using your hands or a fork. Add a generous amount of the prepared frosting to the crumbled cake, mixing until the cake holds together when pressed. You may not need all the frosting, so add it gradually until you reach the desired consistency.
Using your hands, roll the cake mixture into small balls, about the size of a tablespoon. Place the balls on a baking sheet lined with parchment paper. Insert cake pop sticks into each ball, then place the baking sheet in the refrigerator for at least 30 minutes to firm up.
Melt your choice of chocolate in a microwave-safe bowl or melting pot. Dip each chilled cake pop into the melted chocolate, ensuring they are fully coated. Allow any excess chocolate to drip off, then place the pops back on the parchment-lined baking sheet.
While the chocolate is still wet, decorate your cake pops with food coloring, fondant features, sprinkles, or drizzle extra melted chocolate on top. Let the decorations set before serving.
