In May 1988, a woman was arrested outside the Lincoln Tunnel in New Jersey for driving a stolen Porsche. Unable to pay the $3 toll, she explained to the toll collector that she was the wife of David Letterman , and that the young boy in the car with her was David Jr., Letterman’s son. In actuality, the woman’s name was Margaret Mary Ray, and she was being accompanied by her three-year-old son, Alex. The Porsche, however, did belong to Letterman; she’d taken it from his Connecticut home earlier that day.

Thus began Ray’s obsession with the late-night host, which continued into the ‘90s despite multiple arrests. During that time, Ray sent Letterman countless letters and made repeated uninvited visits to his house. One time, police found Ray sleeping near the tennis courts on Letterman’s property.…