David Letterman's Stalker Fan - Who was the woman who kept breaking into the New Canaan, Connecticut home of late night talk show host David Letterman? It was none other than Margaret R. Ray who resided at the time in the town of Danbury. She first drew national attention in the late 1980s when she stole David Letterman's Porsche sports car and claimed she was his wife when stopped at a New York tollbooth. When she trespassed at Dave's home in 1993 (camping out on Letterman's tennis courts), she was sentenced to a few months in prison.. That same year, the state of Connecticut passed an anti-stalking law in response to her behavior. According to a January 1994 Playboy interview, David Letterman said he "tried to get her some psychiatric help, because the state has let her case "fall through the cracks." Ray was later arrested in Westfield, Indiana (15 miles north of Indianapolis) after allegedly trying to steal vitamins and a back pack from a Wal-Mart store. Coincidentally, the arrest site was located near the Carmel, Indiana, home of David Letterman's mom, Dorothy Mengering. On October 6, 1998, newspapers reported that the stalker Margaret R. Ray, 46, ended her life near the small town of Hotchiss, Colorado when she knelt in front of a freight train and was struck by a 100-car train loaded with coal. A year before her death, Ray was arrested in Osceola County, Florida in September 1997 after she showed up uninvited at the home of retired astronaut Story Musgrave (near Kissimmee) and turned on all the outdoor faucets. Musgrave told authorities that Ray had hounded him for years with calls, gifts and letters. David Letterman called her death "a sad end to a confused life." Soon after Ray's death Nellie Ruth Shirley, 39, of South Carolina was charged with trespassing in David Letterman's driveway. And the beat goes on. Anecdotes about Ray's stalking appeared in the book The Letterman Wit: His Life and Humor by Bill Adler (Carroll & Graf, 1995).

TRIVIA NOTE: If you decide to trespass at the home of David Letterman...BEWARE. He's got a sign posted at the end of his driveway nailed to a big tree that reads: "These premises protected by Security Attack Cats." On July, 18, 1989, twenty-one-year-old actress Rebecca Schaeffer, the star of the CBS sitcom MY SISTER SAM was shot and killed by an obsessed fan outside her West Hollywood apartment.

On December 14, 2005, Dave had another crazy fan (Colleen Nestler) come out of the woodwork when a New Mexico judge issued a temporary restraining order claiming that Mr. Letterman is somehow expressing his desire for her through code words ("Marry me, Oprah"), signals and eye gestures. Dave's alleged influence over the women forced her to go bankrupt and caused her "mental cruelty" and "sleep deprivation" as far back as May 1994.

Subsequently, the judge ordered Letterman to stay nine feet away from woman  who demanded that Letterman no longer "think of me, and release me from his mental harassment and hammering." Of course, Letterman's lawyer quickly sought to have the "absurd and frivolous" law suit rescinded.