A fastener for venting gas around the shank of the fastener. The present invention includes various embodiments for venting gases such as combustion gases that seep from a head gasket of an internal combustion engine to the area around the shank of a cylinder head bolt, as one example. The various vent paths include vent paths directly through the bolt, past the bearing surface of the bolted member, or past a washer between the fastener and the bolted member. These vent paths prevent gases from building up in the chamber between the fastener shank and the clearance hole of the bolted member.