CBS' Leslie Moonves Reveals Surprising Side of David Letterman: He's "Extraordinarily Sensitive"

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David Letterman, Leslie Moonves

Amy Sedaris and Regis Philbin also share their favorite stories about the longtime late-night host, who signs off from his CBS show May 20.

A version of this story first appeared in the May 22 issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.

The departure of David Letterman from late night on May 20 will leave a void that, for many, can't be easily filled.

Here three very different showbiz vets reveal their favorite Dave memories, what they will most miss and the iconic moments they feel will land Letterman in the canon of TV legends.

Les Moonves (president and CEO, CBS Corp.)

Dave preceded me at CBS by about a couple of years. But the truth is we went way back. Around 1977, 1978, I was a bartender at the Improv. At that time, I was a mediocre actor who was making more of a living tending bar, and Dave was one of the comedians who'd appear at the club. I knew all those guys — Jay Leno, Freddie Prinze, Andy Kaufman. It was a great time. Dave would come in, but you could tell he didn't like hanging out at the bar. He'd go onstage and then leave.

Flash forward to 1995 when I joined CBS. One of the first things I did was to walk over and see him at the Ed Sullivan Theater. He was always wary of management — both on and off the air! And there I was, the new boss. It was cordial, but it was tough getting close to Dave. Then, a few years into the show, Dave came up with an idea. "Let's do a phone call with Les Moonves and call it 'More With Les.'" They usually happened on a Monday with very little notice! The only time I ever got any sort of advanced notice was when CBS was airing the Super Bowl in Chicago and we were going to try to get Bill Murray — a huge Chicago Bears fan — seats to the game. That was the only sort of semiprepared thing we ever really did. I think those calls helped break the ice with us. I also think Dave was surprised that I could handle myself as well as I did. He'd throw some jab at me and I'd say, "Well the good news is you won't be on the air much longer, so I won't have to deal with this." If you watch Dave one of the things that makes him so brilliant, he really likes his guests scoring points.

I think it would surprise people to know that Dave is extraordinarily sensitive. People see this tough-guy exterior. But he's really careful about not wanting to hurt anybody's feelings or stepping on anybody's toes. He feels like that relative who's not always easy to talk to, but good guy, a decent man. Thank God we got somebody as good as we have taking over for him. That was really important to Stephen [Colbert]. He truly idolizes David Letterman, so it's only appropriate.

Regis Philbin (former co-host, Live! With Regis and Kelly)

I'm going to miss David Letterman in many ways. We've had some wonderful experiences together on his show and off. I'm proud to say that I've been a guest on his show more than anyone else.

When those planes hit the World Trade Center buildings in 2001, late-night comedy shows went off the air, and they didn't know when they should come back. Dave was the first one to return. He called me and asked me to join him along with Dan Rather. It was quite a night.

When I had to have triple bypass surgery, he took over. He set up the hospital, the room, the doctors. Took care of everything, and then that night before the operation, I couldn't sleep so I tuned him in just in time to hear him say, "Regis doesn't know it, but they're going to bust him open like a lobster tomorrow morning." It got a big laugh, but I never got to sleep that night!

One night after his show, we sat on top of his marquee on Broadway and just talked for an hour. It was a wonderful experience. He was the right guy to follow Johnny Carson, who admired him very much. It wasn't the same network, but it didn't matter. Dave will take his place along with Johnny in TV history. I hate to see him leave.

Amy Sedaris (author, actress)

The first time I did the Late Show was in 2001. I was doing a play, Wonder of the World, with Sarah Jessica Parker. I knew Dave was a big fan of my brother David's writing, so I knew he wanted to talk about him!

Being on the show was terrifying because you just respect him so much, but also you got the sense that he was actually listening to you when you were out there. I remember feeling very safe. I'm not a comedian. I don't do stand-up, so I feel like I could be accidentally funny with him and play well off of each other, like being on a date — a date four times a year with the perfect man is what it felt like. That's the kind of relationship I want! Four times a year for seven minutes. He let me talk about my imaginary boyfriends and my rabbits. He let me do whatever I wanted. I just couldn't wait to see him. What more could you ask for? We work! I also loved hearing him say anything personal. If he said he'd been in the kitchen making pasta with his wife or whatever, a million things go off in my brain. "What knife were you using? What kind of pasta were you cooking? What were you wearing?" I was obsessed! We just don't know much about the man.

One time I got bumped because Condoleezza Rice came on the show. Dave's assistant called my apartment afterward because Dave felt bad and wanted to talk about it. There was no f—ing way I was going to pick up that phone! I was petrified. Are you kidding me? I'm not going to talk to him at home! Another time I actually saw him outside doing the show, coming down the stairs in the theater. And I was like, "Oh my God, there he is in real life." And I panicked. Ever since that time, I always brought my stuff from the dressing room downstairs, so when I got finished with my segment I was out that door. I was too terrified of seeing him again. And then I had a business meeting with him! I had a deal with Worldwide Pants to create a show, which he really wanted me to do. Nothing ever happened, but his first question to me was, "What don't you want to do?" I really liked that he said that.

I don't normally get depressed, but after my last appearance I felt really weird. I thought, "God, what is wrong with me?" Then I realized, "I just got out of a 15-year relationship with this man who was really important to me." But I was happy I was able to feel it. Being on with Stephen [Colbert] just won't be the same, not just because I know him so well and we are peers. With Letterman it was like being with somebody I was still getting to know. And so when I try to articulate myself it's hard to talk about it. I know I don't do it justice — explaining my feelings is not my strength. Stephen's going to be great and it's going to be his own show, but that era of Letterman is just, it's like, "Wow, it's really gone."

He once gave me the tassels off his shoes, which I now covet. He ripped them off his shoes and he handed them to me. I turned them into pasties to attach to the outside of my dress, obviously.

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