Up to the 18th century, the prevailing view of reproduction, or ‘generation’ as it was referred to, was that organisms develop from miniatures of themselves, termed preformation. The alternative theory, epigenesis, proposed that the structure of an animal emerges gradually from a relatively formless egg. The teachings of the Ancient Greeks who argued either that both sexes each contributed ‘semen’ to form the embryo, or held a more male-centred view that the female merely provided fertile ground for the male seed to grow, dominated thinking until the 17th century, when the combined work of numerous scholars led to the theory that all female organisms, including humans, produced eggs. The sequence of events leading to the commercial use of artificial insemination (AI) date back to the discovery of sperm in 1678, although it took almost 100 years to demonstrate that sperm were the agents of fertilisation and a further 100 years for the detailed events associated with fertilisation to be elucidated. The first successful AI, carried out in the dog, dates back to 1780 while it was not until the early to mid-1900s that practical methods for AI were described in Russia. Inspired by the Russian success, the first AI cooperative was established in Denmark in 1936 and later in the United States in 1938. The next major advances involved development of semen extenders, addition of antibiotics to semen, and the discovery in 1949 that glycerol protected sperm during cryopreservation. Almost four decades later, the flow cytometric separation of X- and Y-bearing sperm opened a new chapter in the application of AI for cattle breeding. As we look forward today, developments in imaging sperm and breakthroughs in gene editing and stem cell technology are opening up new possibilities to manipulate reproduction in a way never thought possible by the pioneers of the past. This review highlights some of the main milestones and individuals in the history of sperm biology and the development of technologies associated with AI in cattle.