When Steve Jobs wanted to dress up as Willy Wonka

The past few months have provided a treasure trove of information about Steve Jobs, and the latest story involves Jobs wanting to dress up as Willy Wonka to celebrate an Apple milestone

The past few months have provided a treasure trove of new information about Steve Jobs and what goes on behind the scenes at Apple. First, there was Walter Isaacson's biography of Steve Jobs. Second, Adam Lashinsky's Inside Apple gave users an interesting look into the business mechanics behind the Apple machine - remember Apple's secret packaging room?

And now Apple fans who can't get enough have even more reason to celebrate and fork over a few dollars.

Ken Segall, as the creative director of Chiat/Day - Steve Jobs' advertising agency of choice - has had a long and storied history working with Steve Jobs, both while he was at Apple and NeXT. Indeed, the narrative of the iconic Think Different commercial was penned, in part, by Segall. What's more, Segall is also responsible for coming up with the name "iMac", starting the i-naming trend that continues to drape most of Apple's products to this day. Incidentally, Jobs reportedly wanted to call the original iMac something else - MacMan.

In a book set for release today, titled Insanely Simple: The Obsession That Drives Apple's SuccessSegall provides a first hand account of how Apple was able to climb back to prominence after being just weeks away from bankruptcy in 1997.

Not surprisingly, and as evidenced by the title of the book, Jobs was singularly focused on simplicity.

Boston.com noted in their review:

Segall tells us that for Jobs, the secret was simplicity. In every phase of the business, he used simplicity as a competitive weapon — Segall calls it “the Simple Stick.” Jobs wielded the stick against all things excessive or nonessential. Whether it was an extra push button on an iPhone, a wasted word in a magazine ad, or one employee too many at a company meeting, Jobs insisted on utter simplicity.

As one would expect, the book is filled with interesting anecdotes and over the past few weeks, Segall has provided a few of those to fans on his Facebook page. From the full story behind Noah Wyle's famous cameo as Steve Jobs at Macworld, to Jobs' brutal interview methods (which read more like interrogation tactics to be honest), to how Jobs wasn't a fan, at first, of the now iconic silhouetted iPod advertisements, Segall provides an unprecedented glimpse into Apple stories that have largely never been told before.

But one story I stumbled upon thus far really takes the cake. It involves Steve Jobs wanting to dress up in full Willy Wonka regalia.

I kid you not.

Segall explains how Jobs wanted to put together a big production to celebrate the 1 millionth sale of the original Bondi Blue iMac. And seeing as how the original iMac represented Apple's return to relevancy, one can understand why Jobs was so excited. Sure, Jobs could be brutal at times, but the following story illustrates his other and more playful side.

Steve's idea was to do a Willy Wonka with it. Just as Wonka did in the movie, Steve wanted to put a golden certificate representing the millionth iMac inside the box of one iMac, and publicize that fact. Whoever opened the lucky iMac box would be refunded the purchase price and be flown to Cupertino, where he or she (and, presumably, the accompanying family) would be taken on a tour of the Apple campus. Steve had already instructed his internal creative group to design a prototype golden certificate, which he shared with us. But the killer was that Steve wanted to go all out on this. He wanted to meet the lucky winner in full Willy Wonka garb. Yes, complete with top hat and tails.

Those who heard Jobs' plan were reportedly taken by his enthusiasm, but weren't exactly keen on the idea. But as it turns out, a California law precluded the big production from even taking place. Under California law, sweepstakes such as the one envisioned by Jobs must allow people to enter without requiring them to make a purchase. And seeing as how Jobs wouldn't ever fathom giving away iMacs for free, or opening up the celebratory Apple contest to everyone (i.e PC users), the plan never got off the ground.

Oh, what could have been.

Incidentally, am I the only one who thinks this story is hilariously similar to an episode of The Office where Michael Scott essentially implements what Jobs had in mind?

Funny enough, CollegeHumor last year put together a super funny and clever video depicting Jobs as Willy Wonka and taking Apple fans on a tour of Apple HQ. It's worth checking out.

One final note - Jobs apparently had no reservations about dressing up. A little known fact is that the Apple co-founder dressed up as Jesus at Apple's first Halloween party back in 1979.

via MacRumors

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