Bentley is one of the most revered car companies in the world, so how has it gathered such a reputation? It’s one of Britain’s oldest manufacturers, founded in 1919 by W.O Bentley. Despite its current headquarters in Crewe in the North of England, its incorporation was actually in Cricklewood, North London, where its most iconic road and race cars were built.

Yet its grand reputation was not born out of building luxury saloons or the Royal Family’s state vehicles like today. Instead, it was W.O Bentley’s love of racing. Only a few years after its incorporation, Bentley started dominating European sports car racing with its huge and powerful racers like the aptly named ‘Bentley Blower’. It went on to become inextricably linked to bourgeois culture in England, with the legend of the ‘Bentley Boys’ encapsulating the indulgent period leading up to World War II.

By the great depression, however, Bentley’s finances were in a dire state, and after failing to make loan payments was put into receivership before being snapped up by rival Rolls-Royce. W.O Bentley retained his position after the sale, but soon left to work for British company Lagonda.

Today Bentley still represents the upper echelons of the car world, specialising in luxury sports cars that channel its envious heritage. It might not be part of Rolls-Royce, but has in the interim been picked up by the vast Volkswagen Group, forming part of its flagship collection of brands that include supercar marques like Porsche, Bugatti and Lamborghini.

Below we run down 10 of the most important Bentleys in its illustrious history; ones that for different reasons encapsulate the magic of that bygone era.