The time David Letterman licked my iPad (Saying goodbye to Late Show on CBS)

I haven’t seen the final episode of The Late Show With Stephen Colbert. I couldn’t watch it when it aired because at this point I’ve forgotten how live television even works. I do have a dim recollection of having once agreed to schedule my life around being in a specific place at a specific time on the same day of every week for months on end, because that was a prerequisite to seeing episodes of The X-Files…but that can’t possibly be right, can it?

The Colbert show was nice enough to put all of the episode’s segments into a YouTube playlist. I've added it to my YouTube library. I’ve even captured those videos to local storage, just in case CBS pulls them down without any warning.

I’m looking forward to watching the final episode.

Someday.

I want to pretend — for a little while — that the show’s just taking a couple of weeks off. I prefer to linger here with the beautiful delusion that the show is taking a few more weeks off than usual. Colbert will be back. And he’ll be bringing an extended interview with Pope Leo XIV that he managed to keep totally under wraps.

There are so many reasons to be upset about The Late Show With Stephen Colbert’s cancellation. The fact that he never got that interview with a sitting Pope is high on that list. I need to see Colbert giving His Holiness the Colbert Questionert. I bet his answers to “What is your favorite smell?” and “What is your least favorite smell?” would both be “Incense.”

(It’s a pleasant aroma. But when you’re the Pope, there’s just no getting away from it.)

The circumstances around the termination of The Late Show absolutely suck and the absence of Colbert’s wit, creative agility, compassion, and empathy at 11:35 pm will be a nightly reminder of the Very Very Wrong Things that are happening in my country right now.

I’ll get around to watching it soon. But for now, please let me keep right on pretending.

Late Show With David Letterman, and Me

David Letterman’s retirement in 2015 was, at the time, also a bit of a blow. Like many kids who grew up in the 80s, I grew up watching the Letterman show. Letterman, along with the works of Mssrs. George Lucas and Steven Spielberg, was a big pop-culture influence on my squishy adolescent brain and my developing worldview.

For this, David Letterman owes many, many of the people who met me before age, say, 28, a partial apology. Perhaps the generation before mine grew up watching Tom Snyder, and copied his chain-smoking habit. From Letterman, I got the impression that it was wicked cool to react to everything around me with sarcasm, detachment, and a kind of foundational grumpiness. I eventually recognized that this, like smoking an entire pack of Pall Malls in a single sitting, is incompatible with one’s longterm quality of life.

I kicked that habit. But I kept my love for the show. Throughout the remainder of Dave’s run on NBC, and the entirety of The Late Show, Letterman was a critical checkpoint to my workday as a student and then as a journalist. Every night, I took a work break to watch Letterman. An hour later, I’d go back to my desk and decide whether to just wrap things up and call it a night, or press on until dawn. Letterman was like the giant steam whistle in a factory town that rattles every window and gets everybody back to work, or home to bed, on time.

Over time, I even made a few online friends inside the show. I often dropped by The Ed Sullivan Building for a visit when I was in town. And my name sort of circulated around as a guy who knew some stuff about some things and was happy to help out here and there.

Which sets us up for a story.

Some time before the official release of the first iPad, excitement about the thing had reached something of a fever pitch. This was 2010, back when there was so much excitement over the latest Apple whatsit that people would set up camp outside the Apple Store to guarantee that they’d be among the first to own one (and, in many cases, ship it to a country where Apple hardware wasn’t locally available).

It was in this environment that I got a message from one of those friends at the show: did I have an iPad? Because the writers had come up with an idea for a Top Ten list to air sometime during the week of shows just before the iPad’s official Saturday launch.

I told him that, well, if Apple were to give me an iPad weeks before its release date, then I would certainly be under an NDA that would prevent me from even disclosing that I had it…but perhaps he and I should circle back on this in a few days.

In fact, it was already in the bag. Figuratively. I had an appointment to meet with Apple in a NYC hotel room, where I would sign a thick NDA, receive an extended one-on-one briefing, and then leave with my backpack stuffed with an iPad and a pile of accessories.

I ran the request by Apple. Unsurprisingly, they were very much on board with all of this. They gave me all of the permissions I needed. It was all fixed up, and there was much rejoicing all around.

I spent the next two weeks getting to know the iPad and acquiring as much real-world experience with it as I could, given that I was forbidden to take it out into the real world. Amidst all this, I was exchanging emails and phone calls with Letterman’s producers. Everyone was pretty excited about using this iPad on the show. But they didn’t know what it could actually do. Neither did I on Day One, but before long, I became a useful technical advisor.

The day arrived — April 1, no less. I was buzzed through the security desk at the Ed Sullivan Building — this time as a man with an actual show-related function, instead of just a visiting friend of some guy, as usual. I didn’t feel like Mr. Big Shot or anything, but it was a good feeling.

I’d advised them of my responsibility to Apple’s pre-release secrecy and they took my requests seriously: only a couple of writers and producers would get to see and handle the iPad before the show, and they’d arranged a room whose hallway-facing windows were covered in curtains.

I think during the first hour or so, we were just having fun with a cool and nigh-unprecedented new piece of tech.

When I’d first fired it up a week or two earlier, I immediately recognized that the iPad was no mere evolution of an existing product; here was a completely new thing. The executive producers and the staffers were just as electrified by their own first demo and hands-on experience with it. It was a wonderful thing to observe secondhand.

Eventually, we got down to business. The Top Ten list would be “Questions To Ask Yourself Before Waiting In Line For The iPad.” Appropriately, Dave would read it off the iPad. Getting the card scanned and synced to the device’s photo roll was no trouble at all.

The second part of the operation was teaching Dave how to work the iPad. This part was way, way more tricky and the task was complicated by two factors:

1. Dave was, according to the EPs who worked with him every day, so inept with all forms of technology that one was inclined to suspect that he was just putting everybody on. But no: they assured me that if there’s such a thing as a “green thumb” for technology, Dave’s thumb was the color furthest therefrom on the color spectrum.
2. I never got to coach Dave directly, one-on-one. I would demonstrate something and give an instruction to the EPs. They would trot upstairs with the iPad and demonstrate and convey it to Dave. Then they would trot back down to our little saferoom with the iPad and new questions.

Most of my advice and instruction concerned how Dave could possibly screw things up. “Tell Dave that he must not do this; that if he presses the round button below the screen please DON’T PANIC, just look for the app named ‘Photos’ and tap it…you know what? Let me cut down the camera roll so that there’s less chance of Dave getting himself lost…” that sort of thing.

Looking back, the process was like running one of NASA’s Mars rovers. I can’t directly access it, so I needed to make sure I gave it all of the instructions and emergency procedures it needed to conduct its mission autonomously. And then just hope for the best.

Despite Dave’s reputation as a technophobe, it was clear that he liked the iPad. They passed along a comment: “Tell the guy he ain’t getting this back.”

You might be wondering “But why didn’t you just come out on stage during the Top Ten, and work the iPad yourself?”

Well, the producers didn’t ask me. I would have loved to have been a guest — OK, “semi-guest” — on this show that I’ve been watching since I was in high school.

But I thought (then, as now) it’d be gauche to make a demand like that. If the show had wanted an on-camera appearance by Chicago Sun-Times technology columnist Andy Ihnatko, they knew that they’d get a YES!!! before they even completed the question.

No, I was there because I thought this was a super-cool, fun idea, and also because I knew I’d be in for a neat little adventure, with my Amtrak fare and hotel expenses covered. Maybe I missed an opportunity for massive self-promotion, I dunno. But I’m completely happy with my choices.

Nearly all of them, anyway.

Showtime. I was installed in the show’s green room, immediately offstage, so that I could make sure that the iPad was in perfect order before its debut on Dave’s desk, and so that I’d be right there to fix things in a hurry if anything went wrong.

Time for the Top Ten List. Dave started off by talking about the iPad. He brought it out:

“This is it right here. And this is the first one uh ever manufactured. Nobody has one. Now we have number one. Even little Jimmy Fallon doesn't have one and he’s very Internet savvy…”

He managed to flip through the stock photos that Apple pre-loaded onto my device without setting anything on fire:

“It comes with photos of a family. So, you're not buying an unnecessary electronic device. You're buying a family. You're buying a family. That's what it is.”

And then…oh dear…Dave started horsing around with it.

We all know that the iPad rotates its display from Landscape to Portrait mode with a smooth, natural, almost beguiling transition. It looks cool! Dave thought so, too. He kept rotating it on his desk over and over again…

Okay. This show aired on April 1, 2010. Can anybody be 100% certain of their memories from a very exciting day that happened over fifteen years ago? Probably not.

So when I tell you that I recall telling the EPs that the iPad’s power switch was up there at the top and that it was vital that Dave mustn’t hold it down, because doing so would power down the device…all I can tell you is that this is how I remember it.

I do bear some responsibility for what happened. I suppose I didn’t clarify that holding the iPad upside down with its top edge pressed into the desk would, consequently, also press down on that Dangerous Button, and that this might be Bad.

Welp, whatever I did or didn’t explain during my briefing to Dave-by-proxy, video evidence proves that Dave did the thing he shouldn’t have done. He didn’t know what to do when the iPad decided to shut down, but he decided that the funny thing to do in this situation would be to lick it.

He recovered nicely:

“Yeah. Well, that's the iPad. And the radiation this thing gives off is incredible. Really, you're supposed to wear a lead apron when you operate it. Well, at least over your…because that's the area which you know you have to be so protective of. ‘Questions to ask yourself now before waiting in line for the iPad.’ Here we go. Number 10…’What the hell is it?’”

Despite the mid-roll hitch, I felt like it had gone off okay. It was a funny bit, and Dave was being nothing less than Dave. The shutdown was a blip.

I spent the rest of the show in the green room, where the iPad was the star that almost everybody wanted to meet and interact with. Paul Shaffer strolled in. I opened up the piano app for him. His lack of interest made me belatedly realize that yes, of course, his own electronic instruments and gadgets were at least 90x better than this one, and that he’d come in to grab a couple of cookies and run.

Dave’s bit with the iPad was funny. It also strayed somewhat from the messaging that Apple had hoped to convey around this category-defining new product, which had yet to make its first impression upon the world.

I mean, even if Dave hadn’t accidentally switched it off and then licked it, lines like “But the thing is giving off unbelievable heat. Seriously,” ensured that I’d be getting a phone call from Cupertino, sooner or later.

I did. At the crack of 8:30 AM the very next morning.

Apple wasn’t angry! But they were…disappointed.

Here’s another recollection that I must preface with the disclaimer that it happened sixteen years ago and I can’t be 100% certain what I said or didn’t say. But I recall that I kept Apple in the loop about how the iPad was going to be used: Dave was going to read a Top Ten list off of the iPad, at the desk. I think they assumed that I’d be onstage there right with it. Had they known that it would be in the hands of Dave, who’d had a couple of hours of experience handling it, as opposed to me, who’d been using it for a couple of weeks…they might have added some conditions to their approval. Fair. And Apple forgave me; I don’t think it damaged my relationship with the company at all.

The whole thing was a great little adventure and a large set of happy memories. 2008 and 2009 had been terrible, terrible times. I’d lost my mother, and then my father, to terminal medical issues. Bringing a pre-release iPad to the Letterman show planted a joyful flag marking the start of happier times.

I do still regret the miscommunication and/or misunderstanding. First and foremost because (from Apple’s perspective) the results might have indicated a violation of the trust they’d placed in me. In retrospect, if Apple had clearly understood that I was going to be offstage the whole time, they might have made the whole operation conditional upon my appearing right there, in the guest chair next to Dave, as the iPad’s exclusive handler…just like Jack Hanna of the Columbus Zoo coming onstage with a Madrid Speckled Gowser Skunk or something in his arms.

I meant it when I said that it would have been a cheap and crass move on my part to exploit the situation and tell the producers that they could only do the bit if I got to add “Guest (sort of) on Late Show With David Letterman” to my CV. The thought never even occurred to me.

…But if I had been able to truthfully, regretfully, relay Apple’s absolute, non-negotiable condition that they couldn’t use this iPad on the show unless they agreed to make my personal lifelong dream come true? Oh, boy!

Postscript: Some of you might take issue with the title of this post. "But Letterman didn't lick YOUR iPad, did he?" you note. "It was Apple's!"

Well, dear reader, when the time came to return Apple's loaner iPad, I felt that it would be irresponsible to put an Apple employee in the position of handling a device that was partially covered in spit. You will agree with me that substituting the iPad I'd pre-ordered and had never been licked, not even once, and keeping the iPad that was filthy with remnants of talk show host DNA, was the upstanding thing to do.

Sure, it meant that I would be stuck with a permanent memento of a grand little adventure, as well as a photo roll that includes the image of the blue card with the Top Ten List. But such are the woeful burdens of the righteous.