Running the mile race in under four minutes has long been a benchmark for the distance. The significant runners and races from the early 1920’s to the first sub-four minute mile and beyond are presented. In the early 1920’s, Finn Paavo Nurmi was the preeminent racer, he who revolutionized the strategy to run the distance most effectively, clocking a then world record time of 4:10.4 in 1924. In 1931, the post Nurmi era saw Frenchman Jules Ladoumègue first break Nurmi’s long standing world record at 4:09.2, which rekindled the pursuit of the four minute barrier. Races designed to break the world record were held, one such seeing Brit Sidney Wooderson break the record in a specially devised handicapped race with pacers. The four minute barrier was finally broken by Aussie John Landy in a race in Finland in 1954 with a time of 3:58. In what was considered the greatest mile race up until then at the 1954 Empire Games in Vancouver, Landy and Brit Roger Bannister ran the first ever mile race with two men under the four minute barrier, Bannister on top. And finally in a race in Los Angeles in 1956, Joe Bailey ran probably the fastest lap ever in a mile race to that time to win in the first ever sub-four minute mile run in the United States.