The Bentley Boys were a set of wealthy British playboys in the 1920s who shared a passion for fine champagne, playing the horses, and, above all, the then-nascent sport of motor racing. Their parties—at the Savoy hotel or in their Mayfair flats—were nearly as famous as their racing exploits. On one occasion, their enthusiasms converged, as the men brought one of their race-worn Bentleys to the festivities at the Savoy. Among their ranks were doctors, fighter pilots, and other men of means. Many fought with distinction in World War I. As car historian Doug Nye memorably put it: “They lived hard. They raced hard. And one or two of them died hard.”

To fully appreciate their character, you need only scan the short biographies that still live on Bentley’s website. “As a Lieutenant Commander in the Royal Navy, he survived two torpedo attacks,” reads Glen Kidston’s. “He was the sole survivor of a civil airline crash on a flight from Croydon to Amsterdam, re-entering the burning wreckage twice in a brave attempt to save others.” Another Bentley Boy, John Duff, was a war hero, an Olympic fencing trainer, and Gary Cooper’s swordfighting double in Hollywood.

Together, the boys helped drive their namesake’s hasty rise to the pinnacle of their sport. W.O. Bentley had begun making and selling cars in 1919. Just five years later, Bentley took top prize at the second installment of the prestigious Le Mans race, having been persuaded to compete by Duff. Bentley’s cars were tough, fast, and (just as important for a gang of war veterans) British. By the end of the ’20s, Bentley would trounce such Continental rivals as Alfa, Bugatti, and Mercedes by winning four consecutive Le Mans titles—each victorious car piloted by members of the Bentley Boys.

Off the track, however, Bentley was struggling, and by 1925, W.O. sold his company to Woolf Barnato, a Bentley Boy who was the heir to a diamond fortune. During this time period, another member of the Bentley Boys, the dashing former fighter pilot Sir Henry “Tim” Birkin, persuaded the company to build the Blower. W.O., who had stayed on as the company’s designer, believed his cars would win races through bigger and bigger engines—Duff had driven a 3.5-liter engine in the 1924 Le Mans, and Bentley’s 1930 winner was powered by a 6.6-liter. But Birkin—a fearless racer and a rakish fellow famous for his pencil mustache and blue-and-white polka-dot scarf—believed that the better approach was supercharging the engine, in the style of the aforementioned Continental rivals.

Against W.O.’s wishes, Birkin and Barnato urged him to test this theory. But it would take W.O. several steps in order to get there. In 1929, with the company near bankruptcy, Bentley built 50 Blowers, housing a non-supercharged version of the fleet’s then-fastest 4.4-liter engine. Ironically, a Bentley Speed Six won the race, while three 4.4-liter Bentleys finished second, third, and fourth.

Birkin was undeterred. He asked his friend, the heiress Dorothy Paget, to fund still another team of five Blowers, each a study in power and beauty that would be supercharged. Famously loud, and nicknamed the Beast for its heft, the car bore a prominent Union Jack, the Paget family crest, and a bold numeral on the grille.

At first, Birkin’s—and Bentley’s—fortunes seemed to have turned; in 1930 one of his cars completed the race’s fastest lap time, at 6 minutes and 48 seconds, at an average speed of 90 mph. But of the two competition editions entered in that year’s race, neither finished. Birkin’s Blower completed just 144 laps before breaking a piston. (And, once again, another Bentley won the race.) Ultimately, the combination of the Blower’s supercharged engine and tanklike construction just didn’t make for a car capable of winning Le Mans’ 24-hour durability test (though Birkin did eventually steer a Blower to second place at that year’s French Grand Prix).

After that, Paget refused to sponsor another car, and, with the Depression setting in, Bentley was sold again, this time to Rolls-Royce. The Bentley Boys as a team followed suit. Kidston died in a plane crash. Duff died from a horse-riding accident. Birkin went on to set the speed record at England’s famous Brooklands race course driving in a Blower that had been converted to a single-seater.

But the car’s legend lives on, in spite of—or perhaps because of—its failure at Le Mans. There was something noble about Birkin’s efforts, and the car itself remains a thing of beauty, a heavy testament to our eternal desire to go dangerously fast. Not for nothing was it Ian Fleming’s choice for 007’s car in his earliest James Bond novels. And, today, one of the five supercharged Blowers is part of Ralph’s own car collection. Purchased in 1988 and restored to “as raced” condition, it is a bold statement of form and function which, as this season’s Polo Originals collection suggests, serves as a rich source of ongoing design inspiration. In that way, the romance between man and speed continues to roll on.