Bentley Boys built brand legend with racing victories
In the 1920s and 1930s, a group of British aristocrats and adventurers known as the Bentley Boys defined Bentley's sporting heritage. Their victories at Le Mans were celebrated.

Clear victories in the 24 Hours of Le Mans race during the 1920s and 1930s built a lasting reputation for the Bentley brand. A group of drivers, known as the Bentley Boys, combined a high-octane lifestyle with the discipline required for racing.
During an era of drama and dangerous competition, members of the Bentley Boys, including Sir Henry 'Tim' Birkin, Glen Kidston, J.D. 'Benjy' Benjafield, and John Duff, enjoyed public attention. They were known not only for their racing prowess but also for their adventurous spirit and social lives, which frequently filled the pages of newspapers.
Founder W.O. Bentley himself commented on the group's significance: "Few companies have been able to create such a legend and myth in such a short time... bringing so many stories and anecdotes. It gave the company attention and brought color, joy, and excitement to an occasionally dull life."
The Bentley Boys collectively achieved five victories at Le Mans within an eight-year span. For instance, Dr. J.D. Benjafield and Sammy Davis won the race in 1927. John Duff was the first Bentley driver to win Le Mans in 1924. This sporting and daring spirit continues among Bentley drivers today.