The Tomahawk cruise missile, the conventional Air Launched Cruise missile, and the SCUD surface-to-surface missile each made an impact during the Gulf War. The cruise missiles were instrumental in incapacitating the Iraqi electrical network. The SCUD missile was not as successful, but did divert the coalition air campaign. Although never utilized, the sister of the SCUD missile, the intercontinental ballistic missile, was pivotal during the Cold War. Each of these weapons can trace their initiation to the development of the German V-1 flying bomb and V-2 rocket during World War II. The German weapons were not as successful as their antecedents. This paper will inspect the military utility of the weapons during World War II. Initially, the paper will define the actors behind the development, and describe the resulting weapons. Next, the essay will examine the strategy in weapon utilization. The paper will quantify the damage caused by both weapons. Then, the document will describe offensive and defensive countermeasures employed by the Allies. The question of the weapons’ military utility will be addressed. Finally, alternatives to the weapons development, production, and employment will be presented.