The Original Boy Racers

In the Roaring Twenties, the ‘Bentley Boys’ roared the loudest. As the carmaker celebrates its centenary, Ben Oliver tells the story of the gang of playboys, aristocrats and adventurers whose exploits on and off the racetrack cemented Bentley’s legend in the most glamorous era of all

By Ben Oliver

September 24 2019

They were war heroes, heirs, entrepreneurs, first-class sportsmen, pioneers of aviation and carousers of epic scale and ambition. Their vivid, varied and often tragically truncated lives show modern young men just what they might achieve if they spent less time on Instagram. And nowhere more so than their exploits racing Bentleys in the great motorsports competitions of the late 1920s.

Collectively, in just a few short years, they established a reputation for Bentley that probably saved it in the Great Depression and on which it still trades now in its centenary year. They led the accelerated lives of young men of the interwar era. Having made it through the Great War, they saw no reason to slow the pace. And in the 1920s, nothing accelerated like a Bentley.

The original Bentley Boy was Walter Owen Bentley himself. ‘WO’ was no slouch, even if he lacked the means of his best-known customers. Before the War he had raced motorcycles and imported French cars. During it he designed two ground-breaking aero engines for which he was given an MBE and an award of £8,000, which he used to establish his own carmaker in July 1919 at just 31 years old.

The first Bentley appeared in 1921, and in 1923 the first Bentley Boy, John Duff, had the immense foresight to race one at the inaugural running of what is still the greatest, toughest race in the world: Le Mans. Duff, a Canadian, had been badly wounded at Passchendaele, but went on to coach the US Olympic fencing team, and stand in for his friend Gary Cooper in Hollywood swordplay scenes. By Bentley Boy standards, he was a comparative underachiever.

Bentley Boy Woolf ‘Babe’ Barnato at the 1928 Le Mans 24 hours
Bentley Boy Woolf ‘Babe’ Barnato at the 1928 Le Mans 24 hours

He began by racing a vast Fiat that was powered by an 18-litre engine from an airship and named Mephistopheles, in which he set a string of records. He took his more modest 3-litre Bentley to Le Mans. WO thought the idea “stupid”, and that no car could survive a 24-hour race on public roads. Duff went anyway, coming fourth despite a punctured fuel tank, and his achievement and the publicity it attracted persuaded WO to enter a team of works Bentleys the following year. Duff won. Le Mans’ reputation as ‘a British race held in France’ had begun, as had Bentley’s indelible association with it.

The group of wealthy racers, adventurers and playboys who became known as the Bentley Boys then began to assemble. Although Le Mans was their annual focus and the series of wins they would record there was their most tangible achievement, their benefit to Bentley came as much from the glamour that clung to them year-round.

They were the influencers and reality stars of their generation, and although a Victorian-born engineer in a tweed suit, WO had a very modern understanding of lifestyle and brand. “The public liked to imagine them living with several mistresses and, of course, several very fast Bentleys, drinking champagne in night clubs, playing the horses and stock exchange, and beating furiously around racing tracks at the weekend,” he said of his drivers. “Of several of them this was not such an inaccurate picture. I would have been perfectly content to see our cars circulating round Le Mans in inglorious solitude so long as the Daily Mail gave us their front page on Monday morning."

The newly-announced Bentley Blower continuation model  – Bentley is to ‘reverse-engineer’ 12 new versions of the 1929 4 ½-litre Blower
The newly-announced Bentley Blower continuation model – Bentley is to ‘reverse-engineer’ 12 new versions of the 1929 4 ½-litre Blower

The leader of the pack was Woolf ‘Babe’ Barnato, his nickname a wry reference to his prize-fighter’s physique. The heir to his family’s South African gold and diamond-mining fortune, he played first-class cricket for Surrey and was an accomplished boxer, powerboat racer and scratch golfer. As a racing driver WO thought him flawless, saying that he never made a mistake and always took instructions from his team principal. This despite becoming WO’s boss in 1926 when he bought a controlling stake in Bentley, continuing to firehose cash into it as the Depression approached.

Barnato did not have a modern sportsman’s attitude to self-denial, however. His parties at Ardenrun, his Surrey estate, or at his apartment on Grosvenor Square were epic, days-long affairs. Other Bentley Boys took apartments close by, and the southeastern corner of the square became known to cabbies as ‘Bentley Corner’ for the battle-scarred dark green monsters abandoned outside. But Barnato did more in his cars than just race at Le Mans. One was converted for ‘nocturnal’ use, the driver sequestered in a sealed, single-seat booth, and the rest of the car’s cabin laid out as an L-shaped boudoir.

There were steadier Bentley Boys, but not many. Dr Dudley ‘Benjy’ Benjafield was a Harley Street doctor and SCH ‘Sammy’ Davis was my forebear as a writer and road tester on the magazine, Autocar. Despite lacking the raw speed and talent (and cash) of Babe, they scored Bentley’s most famous Le Mans win in 1927. They hastily repaired their ‘Old Number 7’ Bentley, driving it through the night to victory with a torch strapped to its bent windscreen frame.

After Babe, two Bentley Boys really stand out. Sir Henry ‘Tiger Tim’ Birkin was a Royal Flying Corps officer and heir to a Nottingham lace fortune. He was a wild racer – too wild for WO.
When he asked for a supercharged car with even more power, WO refused, reasoning that they could not be made reliable enough to last 24 hours. Birkin then turned for finance to his friend Dorothy Paget, the oddball, largely nocturnal 23-year-old Standard Oil heiress and racehorse owner, who named her servants after colours. Their ‘Blower’ Bentleys – which Bentley has just announced it is to make new versions of, with 12 cars planned – never did win Le Mans, but Sir Tim set death-defying speed records in them, his trademark blue-and-white polka-dot scarf billowing behind him so hard itmust have nearly throttled him.

Woolf Barnato and Frank Clement compete for Bentley at Brooklands in 1929
Woolf Barnato and Frank Clement compete for Bentley at Brooklands in 1929

But perhaps the most romantic of this extraordinary cast of characters was Lieutenant Commander Glen Kidston (grandfather of retailer Cath Kidston). Barnato described him as “the beau ideal of a sportsman. The word fear had been expunged from his dictionary. He was a man about town when in the mood, a man of action in another.”

Kidston was the heir to the Clyde Shipping Company fortune and joined the Royal Navy on the outbreak of war, aged just 15. He led a life even more accelerated than those of his Bentley Boy pals: he was a pioneering submariner and aviator; car and motorcycle racer; and big-game hunter.
While still 15, he was torpedoed twice in one morning, and at 17 survived the Battle of Jutland though his submarine ran aground.

He first entered Le Mans in 1929 and came second, Bentley taking the top four places. He was the only survivor of an early commercial airline crash later that year, kicking his way out of the fuselage with his clothes alight before returning to the burning wreckage in an attempt to rescue the other passengers, including the German prince with whom he was travelling.

Glen Kidston and Babe Barnato celebrate victory at Le Mans in 1930. Below: a 1937 memorial portrait of Birkin by Gordon Crosby
Glen Kidston and Babe Barnato celebrate victory at Le Mans in 1930. Below: a 1937 memorial portrait of Birkin by Gordon Crosby

Despite this he returned to Le Mans in 1930. He and Babe won, his partner setting a record of three entries and three wins, which has never been matched. It would be Bentley’s last official Le Mans entry for 71 years. In 1931 it went into receivership, and had the Bentley Boys not given the brand such glamour and repute, Rolls-Royce might not have rescued it. The Bentley Boys were dispersed, not least by early deaths. That same year, Kidston set a record for a flight from the UK to South Africa, but was killed soon afterwards when his aircraft broke up over the Drakensberg Mountains.

Barbara Cartland, one of his lovers, is said to have fainted at the news. He was just 31 years old. Tim Birkin died in 1933, of a wound suffered at the Tripoli Grand Prix. He was just 36. In eight years, the Bentley Boys won Le Mans five times, set a standard for glamour and adventure in motorsport that modern Formula One can’t approach, and probably enabled Bentley to celebrate its centenary this year. “I don’t think many companies can have built up during such a short period a comparable font of legend and myth, story and anecdote,” WO said later. “The company’s activities attracted the public’s fancy, and added a touch of colour, of vicarious glamour and excitement to drab lives.”