David Letterman: 'And You Wonder Why I'm Retiring?'

·Critic-at-Large, Yahoo Entertainment

We’re coming to the end of The Late Show With David Letterman — 42 shows left as I write, according to @ByeLetterman; follow it on “that Twitter thing” Dave doesn’t understand how to use — and the host is getting more loopy, loose, and spontaneous as each hour is recorded for posterity.

On Tuesday night’s show, Letterman took up a suggestion from a woman in the audience named Monica, and after the scheduled Top 10 list, he did something unscripted. Monica, obviously a nostalgic fan, wanted something thrown off the roof of The Ed Sullivan Theater, an ancient Letterman bit that goes back to bygone days of tossing things like “a runny wheel of brie” cheese from high perches. And so he enlisted writer Bill Scheft (Dave doesn’t do the throwing himself anymore, of course), to drop a couple of cantaloupes off the Sullivan roof. They landed with a satisfying splat. 

As he said on Monday night’s show, “It’s fun having old guys on TV, isn’t it?”
At 67, Letterman is easing into his last show on May 20 with all the lack of grace we might have hoped for. He’ll come out, as he did on Monday, tell a corny joke and then make a few strange noises with his throat to indicate his cheerful disgust with the whole enterprise of joke-telling. Then he capped that off with a sardonic question: “And you wonder why I’m retiring?”

The thing is, there was a spell, about 15-16 years ago, when Dave didn’t seem to have his quintuple-bypassed heart in the game anymore — one almost wished, back then, that he would retire, lest he tarnish his reputation as The Most Original Late Night Host Ever. 

Now, however, having announced the final day, Letterman is full of mischievousness again — it’s as if the thought of impending shuffling-around-the-house-in-his-robe has put a new spring in his step. He’s the opposite of Jimmy Fallon — unlike the clever Tonight Show host, Dave doesn’t pride himself on loving social media. Dave acts his age, or older. When Patricia Arquette came on to plug CSI: Cyber, Dave said, “‘Cyber’ means it’s in outer space?”

It also helps that many of his favorite guests are filing in to pay as much tribute as Dave will allow, and making terrific appearances. Just this week, Kevin Spacey arrived, ostensibly to plug House of Cards, but really to do his dead-on Johnny Carson and Jack Lemmon impersonations. 

When Spacey referred to House of Cards as “appointment television,” Dave shot back that his talk show was “disappointment television.” 

By underselling what he’s doing — basically upholding a tradition of being silly while also occasionally engaging in real conversations that sometimes don’t even involve plugging a movie or a TV show — Letterman is going out strong. If he can sustain it until May 20, it’ll be a wonder to behold. I’ll be watching; you ought to be checking in on him, too.

The Late Show With David Letterman airs weekdays at 11:35 p.m. on CBS.