David Letterman licked my iPad

It’s been five years, and this is the last day when we can all refer to “The Late Show With David Letterman” in the present tense, so I might as well finally tell the story:

David Letterman licked my iPad.

Well, Apple’s iPad, technically.

The first iPad was the most Beatlemania-inducing product Apple had ever announced. The amount of excitement that built up between its unveiling on January 27 of 2010 (by a frail-looking but by no means weakened Steve Jobs) and its Saturday, April 3 release date had somehow managed to exceed that of even the original iPhone. Call it the “Empire Strikes Back” effect: the second release is bound to be bigger, because nobody knew in advance that the first one was going to change the world. People started camping out in front of flagship Apple Stores weeks in advance and the “event” was beginning to dominate the news.

I have a couple of friends who work on the Letterman show. I got an email from one of them a couple of weeks before the special day.

“I don’t suppose you’re getting an iPad early, are you? Because there are some people over here who were talking about how interesting it would be to use one somewhere in the show week, before it’s released.”

“Well, hypothetically, if Apple were, in the near-future, allowing me to have early access to hardware, the terms of my nondisclosure agreement with the company would forbid my acknowledging anything of the kind,” I replied. “But perhaps we should keep in touch.”

In fact, yes: I already knew the day and the time when I’d be meeting with Apple. They were giving me a briefing, a chance to ask a whole series of newbie questions . . . and an iPad, pre-loaded with software and content. Fortunately, this would all be happening very soon, in a hotel suite in New York City, so the timing and the geography worked out just fine.

In the tech press, a nondisclosure agreement is a deal in which a writer or publication gets very early access to software and hardware in exchange for a promise not to write or talk about it before a date that’s convenient for the company. Thus, a couple of days before a product becomes generally available, I can publish something long, in-depth, and steeped in two weeks of hands-on experience and experimentation. Otherwise, I’d have to wait until ship day and then try to sputter out some quickly-written and hastily-researched comments and a promise to say more later. Lots of people are eager to buy something as soon as possible, even on Day One. They need to be well-informed. The NDA puts no restrictions on what I say, so I consider it a big win for myself and my readers.

Ten days before its release, I’d have the most travel-friendly computer ever made. But! Ironically, I wasn’t allowed to take it anywhere, or use it in public. I do take NDAs seriously, which caused complications. I wanted to see how readable the screen was in bright sunlight. My population of my neighborhood is dense enough that I decided not to risk taking it into the backyard. Instead, I took a small hike through a disregarded state park, on a weekday, and spent a half an hour at a picnic table with it. I was observed only by the local wildlife, none of which were known to have any particular interest in technology unless it’s smeared with peanut butter and salt.

(Just to be safe: I made sure that I didn’t smear the iPad with peanut butter or salt.)

My editors at the Sun-Times were in the loop, but nobody else (oh, the lies, lies, lies I was forced to tell for ten days!). I ran the Late Show’s request through Apple at my meeting. Yeah. They were completely fine with my letting the Letterman show in.

I didn’t know precisely what the show would finally do with the iPad. But Apple trusted that I wouldn’t let them drop it off a twelve-story building or put a Donald Trump wig on it or anything else doubleplus ungood. I sent a thumbs-up to my Letterman friend and we made plans for me to stop by the show’s offices with it for a basic orientation session after my meeting with Apple was over.

In between those two meetings, however, I had lunch with a good friend who lives in the city. It was just a week before launch day and, as an artist, she was very interested to know whatever I’ve heard about the iPad. I squirmed and quoted things I’d read on Macworld.com and Engadget, and tried not to shoot incriminating looks at the backpack on the seat next to me. I felt like the murderer in a movie who’s forcing himself not to look at the door of the closet where he stuffed Montague’s body, even when the vicar stoops down and picks up an expensive cufflink off the carpet and notes that it seems to have the missing lord’s crest on it.

(I felt guilty enough that I picked up the check for lunch. Perhaps a little bit too forcefully.)

Eventually, I was inside an office in the Ed Sullivan Theater building. The guest list for the Letterman show’s private pre-briefing was kept very small, at my request, and I had asked for a room with no windows and a door that could close and lock. But before everyone filtered in . . . I made an unboxing video, right then and there. Well, I had little choice, did I? My sample device was in original consumer packaging. Once I’d peeled it free from its birth sac, there was no going back. I asked the early arrivals to huddle in the other side of the room, and not make a sound while I recorded.

Once all of the members of the pre-approved guest list had assembled, the door was shut and locked. I verbally deputized those present into the umbrella of my Apple NDA, in a short, tasteful ceremony that hopefully underscored that if someone blabbed to an intern and that intern posted something to his or her Facebook page and even a quick blurb were to appear on Gizmodo . . . Mr. Ihnatko would appear, to Apple and to others, as a colossal boob and as something less-than-worthy of trust.

And then there was much demo-ing and playtime. Everyone wanted a turn with it. Playtime transitioned into questions about what they might be able to make it do on the show. What could it do with pictures? Sound? Video? How hard would it be to prep it to do X? I’d like to make a joke here about feeling like the guy who ferries the Stanley Cup from one venue to another in a padded case, or Prince Philip, who fulfills much the same function for Queen Elizabeth. But it just wasn’t true; everyone really treated me very kindly and made me feel comfortable.

(Still, it’s a solid, cheap joke, particularly the bit about the Queen. And in this economy, cheap jokes remain by far our best joke value.)

The following Thursday, 18 hours after my NDA expired but still two days before the iPad became available to the world, I was back at the Ed. This time, the door was open and I had ten days’ more experience with the device. The writers and producers had decided that Dave would use the iPad in a Top Ten list. I pitched in as Frank Oz to the iPad’s Yoda: the guy who got things working and made sure that this inanimate object would be full of life when it was time to go in front of the cameras.

I would also act as a Yoda for David Letterman. Dave got a crash course on using an iPad. Alas, it was one of Dave’s right-hand producers who got to ride Dave’s back as he jogged through the swamps of Endor (aka the executive floor of the building). But I coached the producer, the producer ran upstairs and coached Dave, Dave would send him back down to me with more questions, I would send him back up with more answers and cautions . . . on and on through the afternoon. All in all, I have to guess that the whole process was probably pretty rough on the guy’s knees.

Yup, I had a terrific time. I’m avoiding specifics here, because even five years later, I’m not comfortable sharing details from a private office.

But I do have to share one thing Dave said to “me,” through the producer:

“Tell him he ain’t gettin’ this thing back.”

Game and match, to Apple!

Finally, it was showtime. I’d changed the iPad’s lockscreen to the Late Show logo, I’d loaded up the iPad with a scanned image of the blue card with the iPad Top Ten, the battery was at maximum, it was clean as a whistle, there was no content on the device that would confuse the bit or the host, and everything was in working order. We made the journey down to the studio. I handed the baby off to another producer, who moved it to Dave’s desk, and then I retreated to the green room next to the stage. I was standing by in case something went wrong with the iPad, Dave wanted to do something with it that nobody had planned on or prepared for, or the tray of high-end cupcakes they’d placed in the room weren’t being disposed off quickly enough.

Hopefully, there’d be nothing for me to do but sit and watch the show.

The CBS Orchestra, which is always ten times more amazing when you get to hear them play live, started amping up the audience, Dave did his warmup, the band started playing the intro, Dave delivered the monologue, and the clock ticked closer to the Top Ten.

Why on earth did I feel such paternal instincts toward the iPad?

I wasn’t worried, per se, but geez, I really hoped the iPad looked good, and that this inanimate object would have a positive experience. I don’t know how parents do it during recitals. I had it easy. Even if things had gone really, really badly, there was zero chance that the iPad would cry so hard that it would eventually begin vomiting. I resolved to regard the odd behavior of Michael Lohan and other celebrity moms and dads with a bit more sympathy.

The show returned from the first commercial break. Without preamble, Dave announced “Ladies and gentlemen . . . here’s tonight’s Top Ten List . . . the Top Ten questions to ask yourself before waiting in line for the iPad.”

“This is it right here,” Dave said, pulling the iPad from the side of his desk. “We have the very first one ever manufactured. Nobody has one right now. Even little Jimmy Fallon doesn’t have one, who’s very electronic-savvy.”

And then Dave started goofing around a little with it, as anyone could have anticipated. It was all funny stuff and a good time until . . .

. . .

Well. I was watching the monitor closely, of course. It was like being an experienced race car driver watching a lap and thinking “Okay. That driver isn’t skidding yet, but he’s just made a mistake that will throw him off the track in 4 … 3 … 2 … 1 …”

When you’re coaching someone on a new piece of tech, particularly when you know they’re about to use it in a mission-critical setting, you have to identify the few truly super-important points and just keep pasting gold stars around those facts over and over again to encourage the information to penetrate. That afternoon, I tried to underscore a very short list of things that Dave could do that would Cause A Problem. Almost all of them involved the Sleep/Wake button and most of my instructions involved “Just don’t press it. Once he’s tapped the button to wake the iPad, he should just never, ever touch it again.”

(20-year “Late Show” director Jerry Foley, in a beautiful piece posted today on HuffPo, had this to say about Dave: “Among Dave’s many gifts is the uncanny ability to turn the simplest task into something unwieldy. Watch him dial a phone or attempt a tweet.” I had heard various versions of this over the course of the day and it was very much on my mind.)

I coached them through what today is the universally-understood step to wake it up again, and I also warned that the Sleep switch became the “Power This Puppy Down Completely” switch when it’s held down for several seconds. But the predicate of every sentence was “seriously, the easiest thing is just for him to hold the iPad like this and not touch the button. Ever.”

Dave tapped the screen and brought up the digital blue card with the Top Ten. But then, he called an audible and showed off a feature that I think amused him when he was playing with the iPad in his office earlier: how smoothly the contents of the screen rotate when you turn the iPad around.

He flopped it from right-side-up to landscape orientation.

He flopped it another 90 degrees . . .

(Oh, crap . . .)

. . . So that the iPad was upside down.

(Damn)

. . . And now mashing the Sleep button down into the desk.

(Crap and damn).

The screen went dark and that’s when Dave got a little bit flustered. He tried to wake it, failed, and then he accidentally switched it off.

And then, having exhausted all of his most common appendages in the effort to turn it on again, he decided to give his tongue a try.

(Oh, dear.)

He read the Top Ten from the analog blue card instead.

Yeah.

Look, it was all in good fun and neither I, the iPad, nor Apple needed to feel any shame whatsoever. After the Top Ten, a producer rushed the iPad to me and I got it up and running again in seconds. I handed it back with a friendly reminder — in my “Dad voice” — that Dave should Not. Mess. With. The. Sleep. Button. Please.

Here’s the first half of that segment:

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I don’t exactly keep replaying those events over and over again, nightmare-fashion. But yes, I felt a little angst about how “the baby” had done in its CBS network debut, and I’ve sometimes thought about what I might have done differently.

Should I have insisted that I be onstage with Dave and the iPad, and handle the device myself? Or even just demanded to coach Dave directly, to make sure it was all sinking in?

Hmmph.

I really don’t know. If I had been onstage, the iPad would have been operated by a Skilled Professional instead of someone who’d first laid hands on it that same afternoon. That’s true.

But then, as now, I felt it would have been presumptuous of me to just insert myself into the show like that. Apple hadn’t made “Andy must be the only person to handle the iPad” a condition for the Letterman show getting to use it. I think if I’d suggested to the producers that I be on camera with it, even if only to ensure that everything went smoothly, I would have come across as selfish and attention-grabby and exploitative. “You can’t use it unless I get to be a guest on the show. And: you also have to book my Sawyer Brown/Babylon 5 mashup tribute band ‘Some G’Kars Do’ as the musical guest later that same week.”

I sure would have felt that way. In the pre-show Q&A during one of last week’s tapings, an audience member had asked Dave for a free staff jacket. I guess I can’t blame him because they’re really nice jackets. But doesn’t the man feel a little weird every time he puts it on? He had a chance for only one face to face interaction with a broadcasting legend, just one week before he retires . . . and he’d used that opportunity to say “Gimme”?

And if Dave was more comfortable being coached by someone he was totally comfortable with instead of a total stranger, I totally respect and understand that choice. My own social software isn’t optimized for interactions with new humans.

So, no: I’ve no regrets. I and the writers and the producers worked really hard, I thought it was a funny segment (even at the time), and again . . . no one got killed.

Also: I had a lovely adventure. I got to tell Paul Shaffer that I had read and greatly enjoyed his recently-published memoir. I’ve added “Contributed content that aired on ‘Late Show With David Letterman’” to the just-barely-truthful version of my CV that I would write up if I were ever interviewed for a senior creative position at Google or Apple.

And I think I actually stole one of the handtowels from the upscale midtown hotel the show had booked for me. When I left for the theater that morning, I belatedly realized that it’d be good to have a cloth to wrap the iPad in so it wouldn’t acquire fingerprints on its trip to the stage.

It was a righteous kill but the fact remains that yeah, I totally stole that. Sorry.

Dave, if you need some help getting up to speed on your new Apple Watch, let’s definitely get in touch. I’ve got a gaping hole in my daily schedule from the hours of 11:35 PM to 12:35 AM from Thursday onward.