Apple at 50: My 10 most memorable moments

The author (far right) at a certain Apple event 25 years ago.

It’s Apple’s 50th anniversary — you might have read something about that lately. And I’ve been writing about the company for more than half of that time, roughly 27 years if my math is correct. Companies may last a good long while, particularly when they have a track record of great products, but the writers who report on them invariably crumble to dust.

Still, my bones haven’t entirely blown away in the lightest of breezes just yet, so I figured I would weigh in with a few insights gleaned from chronicling Cupertino’s comings and goings for half my existence on this planet. Honestly, I might as well get something out of the deal.

The challenge is, you’ve probably had your fill of listicles chronicling Apple’s Best Products of All Time or the Most Memorable TV Commercials or Steve Jobs’s Most Viral Moments or what have you. I know that I have. Besides, while I know my onions when it comes to Apple, my opinion on the most significant Apple product (the iPhone 3G) or the best commercial (the sage iMac G3 serenaded by Kermit the Frog, naturally) or the most memorable thing Steve Jobs ever said (“Just avoid holding it that way”) carries no more weight than anyone else’s. In fact, there are folks whose Apple knowledge is far more encyclopedic than my own who are better equipped to weigh in on all that.

But what I can do is empty out my reporter’s notebook, with some random stories, stray observations and items I’ve largely kept to myself over the last 27 years. With tech reporting seemingly done with me, there’s no reason to keep this stuff under my hat any longer.

The occasion may call for 50 of these — one for each year of Apple’s existence — but let’s be honest: you’d stop reading after around 17, and I’d be scrapping the bottom of the tank long before we got to the last item or two. (“No. 33: Didja ever notice that Apple employed both a guy called Woz and a guy called Joz? That’s pretty weird, huh?”) So let’s stick with 10 random thoughts about Apple as the company celebrates its golden anniversary.

My Most Awkward Encounter with Apple

Back in 2001, I was handed an original iPod, not long after Apple’s press event to show off its new music player. It’s probably forgotten with time, but the MP3 players of that era weren’t very durable, and if you were foolhardy enough to take one on a run, you ran the risk of skips caused by mechanical shock. And heaven help you if you accidentally dropped one of those things.

The iPod was going to be different, Apple told us. Not only would Apple’s music player have more storage, it was going to be durable enough to survive real world use in a way that rival devices simply could not. So I decided to put that to test, probably ill-advisedly.

I commissioned a more physically active colleague to go work out with that iPod in tow, along with one very specific instruction: be especially brutal with the device. “Let’s find out just what kind of a licking this thing can take,” I remember saying at the time.

It turns out the iPod was pretty durable, though not indestructible. We did manage to damage the device, but only after deliberately tossing it from a moving bicycle. Otherwise, for a 2001-era piece of tech, it withstood a fair amount of abuse before finally succumbing to our more violent impulses. I patted myself on the back for conceiving of a handy piece of consumer tech journalism that would give readers insight into just what they could expect from an iPod in terms of durability and went about my business without giving the story another thought.

At least until Apple asked us to return the iPod.

Companies don’t always do that, as they’re happy to leave review units in the hands of publications for use as reference devices when subsequent updates come along. But occasionally, you do get asked to return the equipment, Q-from-James-Bond-style, and this was one of the occasions. But I held out hope that Apple would agree that proving just how much punishment an iPod could take was enough of a service to more than make up for the non-operable loaner.

Apple did not agree. I don’t remember the poor soul who was tasked with explaining to Apple why their once-pristine iPod was coming back in such a decidedly scuffed-up state, but whoever it was made certain to let the company the name of the dastard who so recklessly ordered the iPod beaten to a pulp. It would be many years before Apple ever trusted me with a loaner device again, and even on those occasions, the hand-off was made with decidedly sideways glances.

The part of the Apple campus I’ve never seen

I’m not a frequent visitor to worldwide Apple HQ, but I’ve been around the place a bit. I’ve even gone inside a building or two, though never uninvited, I hasten to add. I’ve had lunch at one of Apple’s on-campus cafeterias, and let me tell you after also dining at Google’s campus, your tech industry workers are being fed very well.

I have not, however, been inside the Steve Jobs Theater, which seems odd since Apple has been holding events there for the better part of a decade. Part of that’s the nature of my role in covering Apple events — I’m usually coordinating coverage and editing people’s work, and it’s easier for me to do that watching the live stream from the comfort of my office.

The closest I’ve come was in 2017, the very first time in fact that the Steve Jobs Theater hosted any product launch. I was a late addition to the coverage team on hand to look at the iPhone 8 models and the new iPhone X, and as a consequence, I was directed to watch the event from an outdoor overflow area on a nearby TV. Which is how I normally cover such product launches, only without the 90-minute commute.

I don’t know what you remember about that 2017 event — the Apple Watch Series 3 maybe or the Apple TV 4K or one of the trio of aforementioned phones. For me, it’s the smell of fertilizer baking in the warm Bay Area sun on the freshly landscaped area surrounding the Steve Jobs Theater. On the bright side, at tech events for other companies, the smell of manure typically originates from the stage, so Apple has that going for it at least.

Watching an event on a TV outside of the closed doors where the products in question are actually being launched is hardly my most traumatic Apple press event experience, though. That’s a close tie between the iPhone 6s launch, held inside the kiln-like Bill Graham Civic Auditorium, and the 2014 Apple event where I covered the iPhone 6 and Apple Watch preview announcements only to be laid off from my job 24 hours later. Good times.

My favorite Apple launch event

Look, over the course of 27 years, Apple events are going to blend together, particularly when you’ve stopped attending them in person. Nevertheless, a few stand out, especially since i was in the room where it happened.

My very first Macworld Expo in January 2000, Steve Jobs announced he was dropping the “i” from his iCEO title — basically, no longer an interim title, which seemed like a big deal at the time. I was also at the WWDC keynote where Apple held a funeral for Mac OS 9, marking the complete transition to OS X.

But c’mon — there’s only one logical choice here, and it’s the iPhone’s unveiling in 2007. Seeing Apple take the wraps off a completely new product is going to stick in the brain pan, especially since it’s one that’s subsequently stood the test of time. (Folks who were there for the Apple Vision Pro unveiling: I do not think time will be as kind to that moment.) Jobs’ pitch of a combination communication device/music player/mobile phone still resonates. Even AT&T’s Stan Sigman reading his contribution to the presentation off of index cards couldn’t dull the occasion.

My favorite Apple-inspired road trip

If you weren’t around for Apple’s pre-OS X era, it’s easy to forget what a significant shift it was away from the old Mac operating systems to the more modern design and capabilities of OS X — especially after previous efforts to update the OS went nowhere. (For us old timers, “Copland” is more than just a 1997 Sylvester Stallone vehicle or the misspelled last name of The Police’s drummer.) Apple had been working on a new OS for a while, and finally, in the fall of 2000, Mac users were going to get a chance to give it a try.

In fact, the public beta of Mac OS X was going to be revealed at that year’s Apple Expo in Paris, and I jokingly suggested to Macworld’s then-editor that it would be a hoot to send me to cover it.

“I don’t speak a lick of French,” I told him. “I don’t even have a passport. Wouldn’t it be hilarious to fly me over there and watch me flail my way through covering the event?”

“It would be hilarious,” the editor unexpectedly agreed. And that’s how I wound up getting an expedited passport, hopping on a flight to Paris and wandering about an indifferent metropolis without anything resembling a concrete game plan.

The turn-of-the-century tech boom was a hell of a time, kids.

Anyhow, I managed, covering both the OS X news and the surprise launch of the key lime iBook. That said, there was one moment of pure jet lag-induced panic that occurred moments before Steve Jobs stepped on stage to make his assorted announcements: What if, I thought, he delivers this entire speech in French, and I’ve come all this way to not understanding a blessed word he’s saying? Fortunately, whatever multilingual capabilities Apple’s CEO possessed were not on display that day, and I was able to fulfill my journalistic obligations.

My least favorite Apple keynote

Jason Snell and I used to have a running gag back in the days when print, not online, was king and we would reserve a sizable chunk of Macworld’s print edition for last-second coverage of all the Macworld Expo keynote announcements Apple was sure to make. But what would happen, we wondered, if Apple didn’t announce much of anything, leaving us with all those pages to fill and very little to write about.

Our joking Plan B: Run an article called “What Went Wrong?” featuring a picture of various Apple executives shrugging.

We came dangerously close to having to do that at the New York edition of Macworld Expo 2001 where Apple announced… well, some stuff. We got a recap of the recent Apple Store openings — hey, they were new at the time — and a lot of talk from developers showing off OS X native apps for the still-nascent operating system. The lone hardware announcement centered around new Power Mac G4 towers, punctuated by a lengthy discussion of what Apple called the “megahertz myth” to address differences in performance between Macs and PCs. Put another way, Apple’s big product announcement at that Expo was punctuated by an 8-minute deep dive on processor pipelines.

We managed to produce the necessary copy to fill those empty magazine pages that night. But it took some doing.

Apple event celebrity sightings

Attend enough Apple-hosted or -adjacent events, and you’re going to run into famous people. For example, if you walked the show floor of a Macworld Expo in San Francisco any time between 2000 and 2009 and didn’t see comedian Sinbad at some point, I’m guessing you were just popping into Moscone Center to use the restroom.

I’m notoriously bad at recognizing people, but even I can recount a couple celebrity encounters. Once, I waited in line to get in for an Expo keynote standing directly behind Adam Savage of Mythbusters fame. And during the iPhone 6s launch held in the hotbox that was the Bill Graham Civic Auditorium, I stood patiently waiting for a demo of one announcement or another — memory tells me it was gameplay on the Apple TV — when Charlie Rose big-footed his way in front of me and took my turn. Definitely the worst thing Charlie Rose has ever been accused of.

(Glances at Charlie Rose’s Wikipedia page.)

Oh. Um. Scratch that.

I’m told Gwen Stefani was at the 2014 iPhone launch, though I never ran into her or her apparently sizable entourage. But while U2 was busy surreptitiously downloading their Songs of Innocence album to the rest of your iPhones, they were also blowing out my ears at the same event.

Most awkward encounter with an Apple executive

Celebrity encounters are all well and good, but who’s a bigger name star than the men and women who run Apple? I don’t often rate face time with the higher-ups at the company, but there was one time where Tim Cook and I had the briefest of interactions. You will be surprised to learn it did not reflect well on me.

I was leaning against a wall in San Jose’s McEnery Convention Center, waiting for a colleague to wrap up a product briefing, when a gaggle of people strolled by, with Tim Cook at the center of the throng. For some reason, he looked over in my general direction at the same time I was watching him pass by, and that’s how I found myself in a staring contest with Apple’s CEO.

I don’t exactly have the friendliest appearance. My resting face makes it appear as if I’m trying to recall how you’ve wronged me, and if ever I try smiling, it looks like I’ve suddenly remembered. So I decided to offer some sort of gesture to convey a spirit of collegiality — I gave Tim Cook what I hoped passed for an amiable nod of acknowledgement. Judging by the mix of confusion and apprehension that flashed across his face, I don’t think I was entirely successful.

So, Tim Cook, if you’re reading this, and you’re still wondering why that glaring fellow nodded at you at that one WWDC many years ago, rest assured that there’s no ill will on my part.

My favorite portrayal of Apple in a movie

I saw 2013’s Jobs twice, which is probably two times more than anyone outside of Ashton Kutcher saw it. Both times were press screenings for a review I was commissioned to write about the movie. The first screening happened well before the movie’s release and Act Three of the picture felt so haphazard to me that I thought for sure that Jobs would be recut prior to arriving in theaters. Hence, the second screening right before the premiere, in which I discovered, nope, the movie was going to wind up exactly the same.

So Jobs isn’t my favorite picture about Apple, and I have to confess that the 2015 Steve Jobs biopic didn’t resonate with me either. No, for big-screen Apple thrills, I suggest turning to the small screen in the form of 1999’s Pirates of Silicon Valley, a made-for-TV movie staring Noah Wylie as Steve Jobs and Anthony Michael Hall as Bill Gates. (John DiMaggio — TV’s Bender — plays Steve Ballmer, and sadly, we do not get to hear “Developers, developers, developers” in the Bender voice.) Pirates of Silicon Valley isn’t the least bit accurate, but it’s a good character study that has something to say about ambition and our impulses to create.

If there’s a runner-up, I’d steer you toward Golden Dreams, a short video that used to run in the part of Disney’s California Adventure that now houses the Little Mermaid ride. There, you can look in as two seemingly random guys named Steve assemble a rudimentary computer while Whoopi Goldberg looks on, pointedly taking a bite out of an apple.

Goofiest Apple product of the last-half century

By this point, it’s probably clear that I find the off-beat aspects of a company’s history to be just as vital as the landmark hits that everyone talks about. I think we all should be serious about our work without being too serious about ourselves, so the things that are going to stand out to me about Apple’s first 50 years are going to reflect that. And occasionally, Apple has had some fun, too.

How else to explain the moment in 2004 when Steve Jobs — co-founder of the company, lauded visionary, subject of many a profile attesting to his business savvy — stood up in front of a packed house and introduced the world to iPod Socks? Jobs is fully committed to the bit, hailing the socks as a “revolutionary new product.” A hint of a smile flashes on his face as he tries to convince the world that, yes indeed, they need to swaddle their music players in brightly colored socks. “They keep your iPod warm,” Jobs insists, and you might for a moment feel like he actually means it.

We can talk about great Apple products and shake our heads at the few missteps. But life is about fun, and there’s no other way to describe iPod socks.

Most symbolic photo of my time covering Apple

Let’s end by circling back to the original iPod — the launch event, specifically. There’s a photo that makes the rounds in my circle of associates, pulled from the launch event video where the cameras have cut to the crowd. And there, you can clearly see Jason Snell watching as the iPod is unveiled. Seated next to him is Rick LePage, Macworld’s editor in chief at the time, and Jon Seff, another Macworld editor.

I’m there, too, though you wouldn’t know it from that shot. For a long time, I assumed I had been sitting next to Jason, so that I was cropped out of the photo — kind of like a real-life version of that Nathan Fielder meme — “Out on the town having the time of my life with a bunch of friends. They’re all just out of frame, laughing too.” — only in reverse. Here, it’s just me who’s been cropped out of the shot, having the time of my life.

And that seemed like a fitting way to sum up my time covering Apple. The company announces something significant, and I’m right there, if only slightly out of the shot.

Of course, that’s actually not the case. In fact-checking this article, we discovered that I am not seated next to Jason, but rather in the row behind him. And yes, we have the photos to prove it.

Jonathan Seff, Rick LePage, Jason Snell, Kristina De Nike, and Philip Michaels, among others, at the iPod launch event in 2001.

So as it turns out, I’m not as peripheral to this Big Moment in Apple History as memory had once dictated. Turns out Apple can still surprise us all after 50 years, even those of us who’ve seen it all.