Abstract: An improved seal assembly for utilization with earth boring drilling bits employing roller cutters. The improved seal is constructed utilizing two resilient O-rings or other resilient seals engaging opposing surfaces in the roller cutter and the corner formed by the shaft and face of the cutter support. The O-rings are mounted in and separated by a flexible floating ring of slightly harder material than the O-ring material. The flexible floating ring may be coated with or made from a material which provides a low coefficient of friction, permitting the O-rings to rotate therein. In an alternate embodiment of the present invention the flexible floating ring is tapered so that increased loading of the earth boring drilling bit will result in increased compression of the resilient O-rings, thus improving the seal under high load conditions.