Separate the cream from oreos using a knife. Place cookies onto a plate, and creams into a bowl.
Line a 10-ounce glass mixing bowl with plastic wrap. Dip the cookies in milk to soften and arrange the pieces in the bowl.
In a medium bowl, mix cream cheese and sugar until smooth. Add oreo cream, use a hand mixer to mix well until well. Add cool whip and combine with the mixture.
Add the mixture on top of oreo layer. Add one more layer of oreos. Add more mixture on top, just in the middle of the bowl. Add cubed strawberries. Repeat until reach the top of the bowl. End with Oreo layer.
Cover the top layer in plastic wrap, and refrigerate for at least 4 hours.
Remove the plastic wrap on top of oreos, and place a plate on top. Gently turn the bowl over, and lift the bowl together with the plastic wrap.