It was usually the bonafide stars that Letterman regularly felt uncomfortable rapping with. Recently, a colleague of mine wrote a piece where she said she’s both attracted and repelled by successful people. (Same here.) Part of the fun of watching Letterman during the "Late Night" years was how it appeared he was grappling with those feelings on a nightly basis. As much as he didn’t mind interviewing famous people, it seemed obvious that Letterman, chip on his shoulder firmly planted, was intent on reminding them they ain’t better than him. “Don’t waste my goddamn time!” Letterman seemed to be implying every time a celeb sat in the guest chair, with him literally towering over them as a reminder of who the hell is boss—a tradition he continued right until the end.
Don’t think Letterman doesn’t know how much of a tool he was to his guests. Just last week, Letterman and Julia Roberts reminisced about the first time she was on the show, and how she was scared he was going to, in her words, “Benihana me into pieces,” like so many young starlets before her. Luckily, Letterman didn’t go into slice-and-dice mode, but he did wonder aloud what made him be so mean towards his guests back in the day. “I think stupid people annoy you,” Roberts simply said.
As much of an unattractive ball of bitterness Letterman could be, watching him shut down an airheaded celeb for getting too full of him/herself was always gratifying. I recently was going through some old "Late Night" clips on YouTube and came across one where Letterman interviewed Sean Young, who showed up with a sleeveless dress and a lot of armpit hair. When Young was going on and on about the new movie she was in, Letterman, wearing a frustrated stare, just cut her off. “OK, that’s enough!” he exclaimed, waving his hand to shut her up, which she happily obliged.
Jesus Christ, I miss that. These days, talk-show hosts act more like babysitters than conversationalists, merely there to pathetically stroke the ego of whatever entertainer graces them with their presence. Chipper young turks like Jimmy Fallon and James Corden may prefer engaging their guests in goofy stunts and skits that’ll most likely get a lot of YouTube views the next day. But the hosts often substitute interviewing skills with incessant pandering and coddling, making any interview an uncomfortable, repugnant mess to sit through. I honestly can’t watch Fallon when he’s interviewing his guests, with the way he constantly refers to whoever he’s chatting with as “buddy” or “pal” and pointing out how awesome that person is. Fallon is basically an attention-starved puppy dog in a suit, hopping on your lap, licking your face and virtually begging you to like him.
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