A 1960s-era Porsche 911 S on Route 1, Maine
One of the current objects of Dempsey's affection is an early-era Porsche 911 S in an understated shade of gray, which he imagines would be an ideal car for tooling around Bar Harbor and Acadia National Park in his home state of Maine.
"That body style hasn't really changed, it's evolved. And it's just cool," he says.
But it's not just about the 911's familiar silhouette: Dempsey also admires the car's evocative image. "With cars like Lamborghinis, you can offend people if you're driving it outside of Italy. But if you're in an early 911, no matter where you are, people welcome you warmly."