That Time Dave Did His Show Inside a Hotel Room

This week, David Letterman delivered a dispatch from the world of retirement in the form of a lengthy interview with New York magazine. In it he gave us a glimpse as to what he’s up to now, but he also told us what he’s not doing, and that’s catching up on his late night television. Dave doesn’t care about your late night show (given the number that currently exist, there is a chance that the “your” in that sentence actually applies to you). The world of late night has changed significantly since Dave’s time. It is no longer disposable, gone forever once the credits roll. Now every second lives on forever on the internet, demanding you watch the next clip, like, and subscribe. For me, the best place to see this difference is in looking at Letterman’s theme shows. Whether it’s the time he did the show from his offices, pretended to go to Japan, or just rotated the camera for an hour, nobody knew how to turn a standard late night show into an event like Dave.

Today we go back nearly 30 years to November 19, 1987. On this night Late Night with David Letterman did not open from its usual studio in 30 Rockefeller and instead began with Dave standing in the lobby of a standard hotel. “What exactly am I doing here? Well, you know, ever since I was a small boy it has been a lifelong dream of mine to be able to do a network television show from a Times Square hotel room. Or at least that’s what we told NBC in order to have the money to come over here and screw around for an hour.”

After Paul Shaffer and his band perform the theme song live from the Milford Plaza’s Helen Hayes Suite (with electronic drums, of course), Dave gives us a little tour of the 27th floor. There’s the soft drink machine (“her drink of choice was Orange Crush if the cans under the bed are any indication”), the service elevator, the housekeeping cart from which Dave grabs some soaps and rolls of toilet paper since “the holidays are coming up soon,” and then finally we get to see the suite itself.

Crammed inside the Times Square hotel room is a four-piece band, a couch, chair and desk, at least two cameras, a “stage” manager, and sound guy. And then of course in the adjoining room we have the control room where at least six people sit, surrounded by monitors. Dave pops in, asks for an update on the room of stewardesses across the street (Hal informs him that they’ve pulled the blinds down), and predicts that there will be at least one accidental death in the room that evening.

The first order of business when one does a television show inside a hotel, obviously, is to accost other guests and abuse the room service. Dave immediately snaps into action, walking down the hallway, trying each door in rapid succession, but ultimately only finding Jon Godfrey of Albany, NY who was in town on business. As the only guy who opens his door, he is given the lucky position of sidekick for the evening as Dave goes through his talk show host duties such as ordering cheese and crackers for 100 and interviewing Carly Simon.

Carly Simon’s interview is relatively standard fare, asking about her performance process and attempting to get the exclusive on who “You’re So Vain” was written about to no avail. Far more interesting is Carly’s performance of the single from her record. The show is in close quarters already, but when you have three guys playing the keyboards, an acoustic guitar, a set of electronic drums, two backup singers, and Ms. Simon herself, things are going to get cramped. Though the director cuts from camera to camera, Jon Godfrey on the couch somehow ends up in every shot. Eventually, the director gives up and just slowly zooms out from a tight shot of the hotel guest.

We then go to commercial, and just as we return, wouldn’t you know it, it’s Artie from room service, with a cart parked with an enormous amount of food. He begins to unload it, placing a giant order of coleslaw that Dave didn’t order, directly in front of him, and in the process, blocks the camera’s shot of Dave. Ready for everything, as always, Dave reacts quickly and takes us to the Top 10 List: The top 10 things overheard in Times Square. It is at this point that I realized that this was a much different New York City than the one I was familiar with. This was the gritty, peep shows of Times Square era, and the Top 10 jokes reflect that with items such as “Only one person per booth, Mr. Chancellor,” and “I refuse to get on the bus to Ohio until we find the rest of Mrs. Gardner.”

Obviously, the only way to follow Carly Simon is with podiatrist and shoe collector Dr. Ted Borges, who had been scheduled to be on the show several times throughout the week, but kept getting bumped before finally showing up on this program with stacks and stacks of shoes on the table in front of him. Dave starts him off with a pretty standard opening question about his origins: “Were you drawn to this part of the anatomy?” Dr. Ted gives an honest answer and begins, “Well, when I was younger, I had ingrown toenails…” To which Dave responds with a rather visceral, “Oh, God.” He recovers, asks Ted another question, and then cuts the podiatrist off to exclaim: “What the hell are we doing? Room full of shoes, eating bad room service food…” Dave makes it through the segment, showing us LBJ’s shoes, among a handful of other celebrities, but even as the consummate host offers his guest some of the chef’s salad, you can tell he’s just waiting for this particular segment (or perhaps the hotel room episode?) to end.

The final guest, Hunter S. Thompson, is only slightly less of a disaster than the shoe guy. Almost immediately after the interview begins, Thompson decides that he’s too hot in his military jacket and attempts to take it off. Off course, he wasn’t remembering that his lapel mic was attached to his jacket. It’s a bit of a struggle, but eventually Thompson prevails, taking off the jacket and reattaching it to his sweater. Dave once again waits until Hunter is off on another topic before interrupting to ask “Why didn’t you take your jacket off before we started taping?” Besides the open window behind him and the bright lights in front of him, Hunter doesn’t really have a great answer.

The hotel room episode is a strange beast. For most of the episode it feels unruly, nerve-racking, and a little dangerous. It simultaneously feels meticulously planned, but also there are time when it feels like Dave is just going by the seat of his pants. Just as the Times Square Dave talks about in his Top 10 List no longer exists, this version of late night event show is dead as well. First of all, I looked it up and this was on a Thursday. If the Late Night of today were to do a similar theme show, I’m fairly confident that you wouldn’t do it on a school night as opposed to the much more viewed Friday night. And when there are so many opportunities for the program to go off the rails, I’m also fairly confident you wouldn’t attempt such a weird gimmick on your modern-day late night show. Late Night with David Letterman was truly a genre smashing show that tried everything at least once. Sometimes you get the equivalent of a three star meal with your late night concept, but sometimes you get a bad seran-wrapped chef’s salad picked up off the floor.

Ramsey Ess is a freelance writer for television, podcaster and a guy on Twitter. Check out his web series Ramsey Has a Time Machine featuring Chris Elliott!

That Time Dave Did His Show Inside a Hotel Room