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. Another time, she told reporters that she’d left cookies in Letterman’s foyer, along with an empty bottle of Jack Daniel’s.

The Strange Story of the Woman Who Kept Breaking Into David Letterman’s House

For the most part, Letterman said he found Ray’s behavior odd rather than scary and had great compassion for her. There was one instance, though, when Letterman and his then-girlfriend felt threatened by Ray. As the couple lay in bed one Sunday evening, they discovered Ray watching them from out in the hallway.

Upon realizing she’d been spotted, Ray ran off without incident.

Though Letterman occasionally made jokes about Ray on his show, he was adamant about not using her name on-air. “I wasn’t comfortable with the humanity of that,” he later revealed. For example, on his top 10 list of “Things I Have To Do Before I Leave NBC” from a 1993 episode, he included an entry that said, “Send change-of-address forms to that woman who breaks into my house.” Overall, it was reported that Ray spent 10 months in prison and 14 months in a mental institution on trespassing charges.

On October 5, 1998, Ray committed suicide by kneeling in front of a train in Colorado. Following her death, Ray’s mother told The New York Times that she’d been diagnosed with schizophrenia, which had plagued several of her other relatives. When asked to comment, Letterman called it “a sad end to a confused life.”