The Mars Science Laboratory (MSL) rover, Curiosity, completed its first Martian year, 669 sols (687 Earth days), of operation on June 24, 2014. During that time the rover successfully drilled three full depth drill holes into the Martian surface and analyzed the recovered material using onboard instruments, giving us new insights into the potential habitability of ancient Mars. These drill targets are known as 'John Klein' (Sol 182) and 'Cumberland' (Sol 279), which lie in the mudstones of the Yellowknife Bay formation, and 'Windjana' (Sol 621), which lies in the sandstones of the Kimberley formation. In this paper we will discuss what was necessary to procure these samples, including: 1) an overview of the sampling hardware; 2) the steps taken to ensure sampling hardware is safe when drilling into a target (i.e., evaluation of rock type, rover stability, prior testbed experience, etc.); and 3) the drilling parameters used to acquire these samples. We will also describe each target individually and discuss why each sample was desired, the triage steps taken to ensure it could be safely acquired, and the telemetry obtained for each. Finally, we will present scientific highlights obtained from each site utilizing MSL's onboard instrumentation (SAM & CheMin), results enabled by the drills ability to excavate sample at depth and transfer it to these instruments.