Preheat the oven to 350 degrees and line muffin pan with cupcake liners. (I also used two muffin pans, I had batter for 16 cupcakes)
In a bowl on an electric mixer, beat together the oil, buttermilk, eggs, food coloring, vinegar, and vanilla on medium low.
Add the sifted dry ingredients to the wet mixture and beat on low until smooth and just combined.
Add MOST of the crushed Oreo cookies (set aside about 2 tbs to top of the cupcakes.) and stir on low until just incorporated.
Divide the batter evenly among the cupcake cups, filled about 3/4 full.
Bake for 18-20 minutes. Do a toothpick test to make sure the cupcakes are cooked through. Cool completely before frosting.
Frosting: In a large mixing bowl, beat the cream cheese, butter and vanilla together until smooth and light. (about 2-3 minutes)
Lower the speed to low and slowly add the powder sugar. Beat until just incorporated. Increase the speed to medium-high and mix until very light and fluffy. (about another 1-1 1/2 minutes)
Frost the cupcakes and sprinkle with remaining crushed Oreos.