Preheat the oven to 350°F (175°C). Grease a 9x5 inch loaf pan and line it with parchment paper, leaving some overhang on the sides.
In a large mixing bowl, beat the softened butter and brown sugar together using an electric mixer for 2 to 3 minutes until light and creamy.
Beat in the eggs one at a time, mixing well after each addition. Add the vanilla extract and mix until combined.
Add the mashed bananas and sour cream. Mix until combined.
In a separate bowl, whisk together the flour, baking soda, and salt.
Add the dry ingredients to the banana mixture and gently fold with a spatula until almost combined. Avoid overmixing.
Gently fold the chopped Oreo cookies into the batter, making sure they are evenly distributed.
Transfer the batter to the prepared loaf pan and spread evenly using a spatula.
Bake for approximately 55 to 65 minutes. At the 45 minute mark, check the top of the bread for browning. If it is getting too dark, loosely cover the pan with aluminum foil and continue baking. Begin checking for doneness around 50 minutes. A skewer inserted into a section of bread without Oreo pieces should come out without wet batter.
Allow the banana bread to cool in the pan for 15 minutes before transferring it to a wire rack to cool completely.
In a small bowl, whisk together the powdered sugar, 2 tablespoons of milk, and vanilla extract until smooth. Add additional milk a little at a time until the glaze reaches a thick but pourable consistency.
Stir the finely crushed Oreo cookies into the glaze until evenly distributed.
Spoon the cookies and cream glaze over the completely cooled banana bread, allowing some to drip down the sides.
Immediately sprinkle the chopped Oreo cookies over the glaze before it sets.