Today we discuss some of the most rakish daredevils in racing history, a group that charged their own era in Le Mans racing, some British privateers that not only grabbed headlines but also trophies. Today we discuss the Bentley Boys, their antics and their victories.

Between 1923 and 1931, a loose fraternity of British gentlemen drivers—the “Bentley Boys”—won Le Mans five times and stamped a rakish, champagne-and-castor-oil identity onto motor racing. Their success flowed from a simple formula: W.O. Bentley’s mechanically conservative but brutally durable cars, coupled with drivers who could push them at an unflinching pace for a full day and night.