Monroe piercing pain is considered to make 4 out of 10 points on the pain scale. The pain level also depends on the individual characteristics of your lip. Visit a professional piercer to perform your Monroe piercing 2.Professional piercers perform Monroe piercings at a small gauge, usually 16, which leaves a scar that resembles the size of the head of a pin 2.A nonprofessional or novice may pierce your upper lip with a needle and jewelry that is too large for your anatomy, causing a large scar. The Monroe piercing is designed to mimic the beauty spot that appeared above the upper lip of the famous actress Marilyn Monroe. The piercing goes through the upper lip and off to one side. How to Take Out a Monroe Piercing. A Monroe piercing, also called a Madonna piercing, is named in honor of these celebrities' beauty marks. The jewelry worn in a Monroe piercing is a labret stud. It is a relatively painful procedure, as there are a lot of nerves endings in the inner lip zone.