Boisdale Life Magazine (Issue 18) - Page 60

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
hey 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
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
Sir Henry ‘Tim’ Birkin
fencing team, and stand in for his friend
Gary Cooper in Hollywood swordplay
scenes. By Bentley Boy standards, he
was a comparative underachiever.
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

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