A Bentley Blower from England to France

Though Dempsey embraces the technology that makes his Porsche 911 GT3 RSR a beast on the track, he's also a bit nostalgic for that romantic age when gentlemen racers took big risks in uncomplicated contraptions.

"Go back to the 1920s and take a Blower Bentley from England to France. That would be a great one," he says. "The Bentley was such an important car for the time and place because it was there for the first decade of Le Mans, and it gives the Brits a connection to Le Mans like nobody's business."

Dempsey has long admired the glamour and grit of old-school racers: "The Bentley boys partied hard, but they were also very professional, and that's what a lot of people don't remember. They dominated that era."