The chip formation in machining operations is commonly accomplished by a combination of several elements working together to complete the job. Among these components, cutting tool is the key element that serves in the front line of cutting action. Cutting action becomes a challenge when it comes to machining difficult-to-cut materials. Titanium and its alloys are among the most difficult-to-cut materials which are widely used in diverse industrial sectors. This chapter aims to provide a historical background and application of different cutting tools in machining industry with a main focus on the applicable cutting tools in machining titanium and titanium alloys. Selection of appropriate tool material for a certain application is directly influenced by the characteristics of material to be machined. In this context, a brief overview of the metallurgy of titanium and its alloys is also presented. Recent progresses in tool materials, appropriate tools for cutting titanium alloys, and their dominant wear mechanisms will also be covered in this chapter.