David Letterman

"We've done over 2000 shows. You do that many shows, some are gonna suck, some are gonna eat, and some are just gonna blow."

David Letterman began his career in broadcasting in Indianapolis, Indiana, working as a weekend weatherman. In 1975, he moved to Los Angeles and wrote comedy, appearing on Mary Tyler Moore, The Gong Show, and $20,000 Pyramid. His stand-up routines alongside Jay Leno led to a 1978 appearance on The Tonight Show with Johnny Carson, and ultimately Letterman's flagship broadcast, Late Night with David Letterman.

CUSTOMER:
Hi. Can I have two cheeseburgers and a small order of fries.

LETTERMAN:
You know, ma'am, we're really busy. Can I
ask you to circle the lot once or twice so we can kind of collect ourselves here? If you don't mind, it would really help us out a lot. We're just up to our necks here.

CUSTOMER:
Who is this?

LETTERMAN:
None of your business. Just circle the lot and we'll pick you up the next time, all right? Circle the lot.

The car takes off and circles the lot. Later he gets a job at Taco Bell, announcing that meals for Mexicans are half price.

It's remarkable how little is known about David Letterman's personal life. Often people extract what they can from stray cameos in movies like Chris Elliot's Cabin Boy, where he played a sarcastic villager who calls Chris Elliot "Jennifer". In films like Man On The Moon and Private Parts, Letterman prefers to appear as himself. To this day he remains intensely private, but periodically leaks information during polite, intimate interviews. He has a fondness for old British films—actress Myrna Loy in particular—and tales of unrequited love. The original versions of Goodbye, Mr. Chips and The Ghost and Mrs. Muir reduce him to tears. Beavis and Butt-Head makes him howl with laughter.

STERN
You don't have a driver?

LETTERMAN
No, I don't have a driver.

STERN
That's the whole thing. Dave likes to drive his own car. Dave, look at me. I want some eye contact.

LETTERMAN
I have to look at you?

STERN
Yeah, you have to look at me.

LETTERMAN
Oh, Howard.

Stern appeared on Late Night in gold, glittery drag, further reducing the need for intimate eye contact.

Dave's acerbic, potentially explosive interviews with guests were the precursor to Howard Stern's regular dispatch of Stuttering John—and it didn't always win him friends. At times the show proceeded with the pace of an improvisational train wreck. Cher called him an asshole. During a July 1987 appearance, actor/auteur Crispin Glover stumbled on stage wearing a disturbing wig. Glover clutched a portfolio of eye diseases and made a half-hearted effort to kick Letterman in the head.

One of the more remarkable happenings on Late Night was a guest appearance by actress Drew Barrymore, who wished Dave a happy birthday by performing an impromptu go-go dance on his desk and flashing her tits. Dave's stunned response: "I can't thank you enough for that."

Margaret Ray was a Connecticut woman with a long history of mental illness and a rap sheet dating back to 1988. She wrote Dave a letter every day for six years. She showered him with flowers, cookies, and empty Jack Daniels bottles.

"Sometimes three or four letters a day. And you can see, when she's on medication she makes sense. She's an intelligent woman; she just happens to be insane. When she goes off the medication, you get reams of scrawl—literally, scrawl."

Then she began circling in all the regular stalking patterns: breaking into his home, puttering around in his tool shed and sleeping in his tennis courts. She stole his Porsche, and when she found herself unable to pay the $3 toll near the Lincoln Tunnel in New York, she was arrested. Ray identified herself as Letterman's wife and the mother of their (nonexistent) child. "I love him and want to spend the rest of my life with him," she said from jail. She spent 10 months in prison and 14 months in a mental institution.

"The thing is, she's insane," Letterman told a Connecticut newspaper in 1992. "And you don't want to do anything to make it worse than it is."

But he poked fun at her regularly. Top Ten things to do before switching to CBS? Send change-of-address forms to that woman who breaks into my house.

Ray would be arrested seven more times for Letterman-related antics before shifting the focus of her adoration to retired astronaut Story Musgrave. She banged on his front door at 5:30 in the morning, and then went around the house turning on all the water faucets. Weeks later, Margaret Ray committed suicide by kneeling in front of a train in Colorado.

Letterman's only comment: "This is a sad end to a confused life."

Besides Margaret Ray, up to fifty other women have been known to think Letterman speaks directly to them through the blue glow of their television. Some wait for Dave outside the studio, others at his home. One even managed to throw him up against a wall for a prolonged make-out session. Less than a month after Ray's death, Letterman would have a new stalker: Nellie Ruth Shirley, age 39. She was ordered to stay away.

Hear what Dave had to say about the World Trade Center attacks.