29 April 2025

Epitomising the era perfectly, the Bentley Boys were a group of wealthy drivers who dominated motorsport in the 1920s – and at the Le Mans 24 Hours race in particular.

Featuring both the financial clout and skill behind the wheel, the Bentley Boys became an unofficial collective, not only racing successfully, but also influencing the manufacturer significantly.

The Origins of the Bentley Boys

Set against a period of optimism, affluence (for some), and adventure, the Roaring Twenties could almost be summed up by the Bentley Boy’s exploits. And of course, their successes set up significant foundations on which Bentley – as a car manufacturer – were built.

W.O Bentley founded Bentley Motors in 1919, and the powerful models – such as the Bentley 3 Litre and Bentley Speed Six – quickly became recognised for their performance and engineering. As such, these were some of the most sought-after models amongst wealthy motorists.

And as Bentley wanted to go racing, so did his customers – the crucible of motorsport helping develop the machines further; none more so than the Le Mans 24 Hours, which had already gained a reputation as one of the toughest and most prestigious races around.

The Drivers

A mixture of playboys and aristocrats who came together over their love of racing, the Bentley Boys were primarily made up of:

• Sir Henry ‘Tim Birkin, a former fighter pilot
• J.D. ‘Benjy’ Benjafield, a Harley Street specialist
• SCH ‘ Sammy’ Davis, a racing journalist
• Glen Kidston, record-breaking aviator
• Woolf Barnato, heir to a diamond magnate
• Frank Clement, recruited by W.O. Bentley as a test driver
• John Duff, Canadian racing driver and former soldier
• Bernard Rubin, Australian heir to a pearl magnate

Although not a comprehensive list, it must be said that, despite the playboy nature of many of the Bentley Boys, most served with distinction in the Army and Royal Flying Corps during WWI, giving a hint as to their bravery.

Success at Le Mans

The Bentley Boys' fame largely comes from their achievements at the Le Mans 24 Hours race. In 1924, Bentley's first victory at Le Mans came with a team of drivers, including John Duff, who drove a Bentley 3 Litre to first place.

In the following years, the Bentley Boys continued to dominate the event. They won Le Mans again in 1927, 1928, and 1929 with the Bentley Speed Six, and it was the experience and feedback from previous events that helped shape Bentley to last the race distance.

Bentley Boys’ wider impact

The Bentley Boys' success wasn't just about victories on the racetrack – it was about the culture they created around racing. Their association with luxury, speed, and adventure helped elevate the image of both Bentley and motorsport in general. They turned racing into an elite social event, where the wealthy could not only show off their cars but also test their skills against each other in a battle of speed and endurance.

For example, one of Bentley’s most famous stories comes, not from the race track, but from a bet. 1930 saw the creation of unofficial races against ‘Le Train Bleu’ – the express that took Brits to the south of France for some Mediterranean sun.

Early in the year, Rover set a precedent by publicising a race from Cannes to Calais, with Dudley Noble managing to cover the distance just over 20 minutes faster than the train’s 20 hour run. More famous however is Barnato’s run in his Bentley Speed Six.

He had already become chairman in 1925, but in March of 1930, Barnato argued over dinner at the Carlton Hotel in Cannes that Rover’s success over the Blue Train was not particularly special. He wagered £100 that, not only could he beat Le Train Blue from Cannes to Calais, but he could reach his club in London before the train reached the north French port.

The following day, he put his theory to the test, setting off at 5:45 pm as the train left Cannes Train Station. In typical fashion of the time, he and relief driver Dale Bourn finished their drinks and set off. Heavy rain around Lyon threatened to scupper the challenge, and in the early hours of the morning around Auxerre they struggled to find the refuelling spot – Barnato having called ahead and planned for sites to be open so he could refuel along the way.

Despite also battling a puncture and dense fog, they reached Boulogne at 10:30 am, in time for the cross-channel ferry. They reached The Conservative Club in London at 3:20pm – four minutes before Le Train Bleu reached Calais. The French authorities fined him far more than the £100 he won, but the story was already told.

Their Legacy

The 1930s saw a decline in Bentley's racing fortunes. After the economic downturn of the Great Depression, the company was taken over by Rolls-Royce in 1931. Despite this, the Bentley Boys' legacy continued, with many of them remaining involved in motorsport or continuing their lavish lifestyles, and the brand remained associated with prestige and performance.

The Bentley Boys remain an iconic part of motoring history, representing a golden age of British motorsport. The spirit of competition, camaraderie, and refinement that they embodied continues to resonate in the world of luxury automobiles today.

In fact, the name was resurrected with Bentley’s return to Le Mans in the early 2000s, culminating with victory at Le Mans in 2003. Eleven drivers were involved in this new racing era: with five British drivers - Mark Blundell, Martin Brundle, Johnny Herbert, Guy Smith and Andy Wallace – joining Dane Tom Kristensen, Belgian Eric Van de Poele, American Butch Leitzinger, Australian David Brabham, Italian Dindo Capello, and Monagasque Stéphane Ortelli.