Our list of ten most painful places to get a tattoo: 1  Down Under - nuff said. 2  Spine - Thin skin, close bones, and nerves! 3  Lips. Foot - Thin skin, close bones, and nerves!  Chest/ 1 Ribcage. Behind the ear - Thin skin and close 2  bone! Eyelid. 3  Eyebrow. 4  Elbow. Inside  of Wrist.