Cupcakes
Preheat the oven to 350 degrees F. Line a 12-count cupcake pan with liners and set aside.
Whisk the flour, sugar, baking powder, and salt in a large bowl and set aside.
In a medium bowl, combine butter, oil, sour cream, milk, eggs, and vanilla extract and mix until well combined.
Add wet ingredients to dry and stir until just combined. Do not overmix.
Fill the lined cupcake pan just ⅔ of the way. Bake for 15-20 minutes or until a toothpick inserted into the center of the cupcake comes out clean.
Allow cupcakes to cool for 5 minutes in the pan before transferring them to a wire rack to finish cooling.
Frosting
Beat butter with a hand or stand mixer fitted with a paddle attachment until smooth.
Add the powdered sugar and vanilla and beat until well combined. Add milk one teaspoon at a time until the desired consistency is reached.
Divide the frosting into three even portions. Add the purple food color to one part of the frosting and mix until well combined. Repeat the process with the green and orange food color with the two remaining portions of frosting.
Add each color to a separate piping bag fitted with a large round piping tip.
Decorations
Place an unwrapped Hershey's Kiss chocolate on top of the frosting and press down to create the witch's hat. Add a ½ tablespoon dollop of purple food color to the center of the top of four Oreo thin cookies. Repeat with orange and green frosting to create four hats in each color.
Press a pretzel stick into the bottom of one of the tootsie rolls. Bend the tootsie roll in half, creating a 90-degree angle. Use your fingers to create a boot shape with the tootsie roll. Make a slight indentation with a butter knife to create the boot heel.
Assembly
Use a cupcake corer or small paring knife to create a hole in the middle of the completely cooled cupcakes (be careful not to cut through to the bottom).
Add one tablespoon of purple sprinkles to the hole in four cupcakes and replace the cupcake' lid'. Repeat the process with the green and orange sprinkles on the remaining cupcakes, so there are four of each color.
Frost the cupcakes filled with the purple sprinkles with the purple frosting. Repeat with the green and orange cupcakes.
Place the purple witches' hats on the purple-frosted cupcakes. Repeat with the green and orange witches' hats.
Stick two of the witch's legs into each cupcake at opposite angles to create the crashed witch.