A 1963 Porsche 356 in Malibu
Credit: Ed Callow

Dempsey did exactly what you'd expect a bona fide car nut to do when he got his first significant paycheck: He bought his dream car. For Dempsey that was a 1963 Porsche 356 Cabriolet, which he still drives and still believes is best suited to sun-soaked Malibu, California.

"I bought the car right after I did 'Can't Buy Me Love,'" a 1987 flick whose title didn't apply to his black bathtub Porsche. "The car was on the side of the street with a 'For Sale' sign for around $9,000, which was probably all I made on that movie."

Why has the 356 endured in Dempsey's stable for more than a quarter century? "It's been one of the most reliable, enjoyable cars to drive," he explains. "Going down the coast in that car is so iconic, so cool and timeless, that it just hits the vibe perfectly."