The Slow Goodbye

I've been watching David Letterman's final shows. Some of them, like when Michael Keaton was on, make it sound like Dave has some terminal illness and we have to tell him now how much we love him because we'll never see him again. I've been waiting for some guest to say, "You know, Dave, I'm really looking forward to seeing what you do next."

He's been running clips of memorable moments from the past. They're funny but they also remind you of the kind of thing he used to do and hasn't even attempted for way too long. An awful lot of the tributes to Dave — like this one by Conan O'Brien — seem like they're trying to ignore everything since around the year 2001. I saw one that mentioned the suit of Velcro (that was 1984) and dropping stuff off a building.

He started dropping things off buildings (or as a witty variation, crushing them with a steamroller) in 1985. It wasn't the cleverest idea — Hey, remember when ABC tried a prime-time game show based on that premise? — but it was funny a few times. Well, Dave's still doing it except he long ago started having someone else do it for him. Talk about minimal effort.

Want to remember Dave at his best? Tomorrow night, Ray Romano is hosting a 90-minute special of clips, including some from the NBC days. My pal Vinnie Favale put it together, probably without ample time, and at least one person I know who's seen it says it's excellent. I have my TiVo primed to grab it and you should do as I do. Here's a preview…

On his recent shows, Dave has made a few remarks about how announcing his retirement was a colossal mistake…as if he really had the option of staying much longer. As I see it, he has several problems now in terms of doing something else, performing-wise, once the show is out of his life. The biggie, of course, is what to do.

If you're in Letterman's position, you don't want to do just anything. It would be pretty embarrassing to follow a 30+ year run on broadcast television with a low-budget cable series…especially a low-budget cable series that didn't do well. Having been in a position where the top box office stars and political figures fought to get in your guest chair, you don't want to sully the memory of your old show by doing a version of it which has a fraction of the budget and the biggest guest you can get is Abe Vigoda.

So you want to do something that won't be a direct comparison to the old show…and the problem with that is that Dave has never really shown any aptitude (or interest) for anything but that old show and that format. He doesn't act. He doesn't host game shows or reality shows or shows that are not basically about David Letterman.

Jerry Seinfeld and Jay Leno have come up with successful Internet/cable programs but Jerry and Jay are guys who've been out doing stand-up and other things all these years. Their current shows are their secondary gigs — the things they do on the side when they aren't making towering piles of money doing stand-up dates. They have active, successful careers without their car shows.

Dave hasn't done real stand-up since it was an ordeal he suffered through to become a talk show host. The closest he's come is those short monologues he does, often without apparent joy, to an audience that loves him so much, they laugh when all he does is to repeat jokes from the previous night's monologue. I think he could do what Seinfeld and Leno do but it would involve traveling and strange audiences and unfamiliar surroundings…and a lot more effort than he's shown doing his own program for a long time. I doubt he even wants to do that.

Further complicating the problem of Letterman finding a new vehicle is that for many decades now, he's operated in an environment of almost total control. He's had a staff he's comfortable with, a staff that's 100% loyal. He's had darn near absolute say on everything. His show settled into its routine because that's the way Dave wanted it.

Could he function in a new environment? You need a new environment if you want to do a new show. Even if you bring a lot of your old crew along, you need new people for a new show (some of whom might suggest things you don't want to do) and new challenges and new decisions and new locations and new problems. I'll bet that's the biggest obstacle of all to a new David Letterman show somewhere. That doesn't mean there can't be one…but if there can't, that's probably why. It would probably even involve new employers since he and CBS don't seem to have come up with anything.

If I were at HBO or one of those channels, I'd go to Dave and offer him a weekly, well-funded and promoted hour on one condition: That the show be full of things he hasn't been doing on CBS since 1993. It couldn't be the same show unbleeped…and if he's as out of ideas as he jokes he is, then they bring in clever writers and producers and Dave has to do some of the things they want him to do. Steve Allen was willing to let his staff stick him in unplanned situations with guests he didn't okay in advance, and force him to ad-lib. Steve Allen wasn't more talented a talk show host than David Letterman, even Dave at his current age.

The odds of Letterman doing something like this? I'm guessing about the same as the odds of us seeing President Carly Fiorina.

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The one thing I do like about the last shows I'm watching is that since it's a procession of Dave's Favorite Guests, we're getting a slightly more interested host who doesn't look totally bored with those he has to interview. A few weeks ago, CBS released this list of stars who'd be guesting with D.L. before he left the air on May 20…

Oprah Winfrey, Bruce Willis, John Travolta, Howard Stern, Martin Short, Jerry Seinfeld, Paul Rudd, Ray Romano, Julia Roberts, Don Rickles, Steve Martin, Michael Keaton, Scarlett Johansson, Jack Hanna, Tom Hanks, Tina Fey, Will Ferrell, Robert Downey Jr, George Clooney, and Bill Murray.

Since that list was released, he's had visits from Travolta, Willis, Seinfeld, Rudd, Martin, Keaton, Johannson, Hanna and Downey. We can also cross off Ferrell, Short, Fey and Romano because they're on next week's schedule…

Mo 5/4: President Barack Obama, Will Ferrell, the Avett Brothers, Brandi Carlile
Tu 5/5: Reese Witherspoon, Nathan Lane, Mumford & Sons
We 5/6: Martin Short, Norah Jones
Th 5/7: Tina Fey
Fr 5/8: Ray Romano, Brian Regan, Dave Matthews Band

Another name on the list could appear on Thursday but there will more likely be a musical guest in that slot. So that leaves Oprah, Stern, Roberts, Rickles, Hanks, Clooney and Murray — seven guests…and Dave has eight more shows. It's hard to believe that Regis Philbin won't put in an appearance so that would be eight guests, plus Dave has reportedly invited Jay Leno and Brian Williams to drop by. I'm curious to see how they schedule them and who else they bring on in the "secondary" guest category like Marv Albert or Jeff Altman. They could "double-up" a few of those "special" guests and have two a night, though I believe some of them wouldn't appear with Howard Stern. (We have one bit of info: Don Rickles' website says he's appearing with Dave on May 11.)

I really hope Dave's last show is wonderful. And I really hope he says or does something to indicate that he's not going to spend the rest of his life in Montana, far from a television camera. He's too talented and he has too many years left when he could be doing something. I'd settle for almost anything but the show he's been doing over and over again for this entire century.