Few high-profile luxury brands have as checkered and tenuous a history as Bentley. Founded in 1919 by W.O. Bentley, his cars quickly caught on with the British aristocracy who wanted to go racing. The group known as the “Bentley Boys” dominated European racing in the 1920s, setting world-speed records and winning the 24 Hours of Le Mans five times between 1924-1930. By 1931, the Great Depression had bankrupted Bentley, and it was absorbed by Rolls-Royce in an attempt to neutralize its competition. For decades, the brand languished, relegated to selling badge-engineered cars that were little different than their Rolls-Royce cousins. New ownership in the 1980s began a reboot of Bentley’s performance heritage that was kicked into high gear when the brand was separated from Rolls-Royce and sold to the Volkswagen Auto Group in 1998.
Since then, Bentley has re-committed to building big, luxurious performance cars with reckless abandon. The results have been an astounding success, with year after year of record-breaking sales numbers that make the bad old days feel like a long time ago. The 2015 Continental GT V8 S has journalists in Britain and America calling it the best Bentley ever, and shows how far the marquee has come in just two decades.
Bentley’s complicated past is filled willed with world-class performance cars that stand in stark contrast to the brand’s buttoned-down image. Here are the 10 cars that Bentley built its performance reputation on.