A stylized writing instrument which is shaped like a proprietary and/or familiar object. In general, embodiments of the invention include a housing shaped like the proprietary and/or familiar object, a writing element, and internal mechanisms provided within the housing for extending the writing element from, and retracting the writing tip into, the housing. The internal mechanisms may comprise a wide variety of actuation systems for extending and retracting the writing element, including a cam actuation assembly, an edge slide actuation assembly, a gravity actuation assembly, a pressure actuation assembly and a push button actuation assembly.