Music and John Cusack seem to go hand in hand. Who can forget his career-making turn in Say Anything, when he used a massive boom box to “serenade” Ione Sky under her bedroom window? Or his monologue about relationships and crafting the perfect mixtape in High Fidelity?

Well wouldn’t you know, after that last one filmed, Cusack was contacted by Steve Jobs. Dishing about the experience on Jimmy Kimmel Live!, the actor explained that the erstwhile tech legend wanted to hire him for a new commercial, and so he offered something that is extremely rare in tech circles — a glimpse at two new, yet-to-be-launched products. The actor got a tour of two projects that would later become iTunes and the iPod, by none other than the Apple honcho himself.

So what did he do next? Well, he didn’t invest in Apple stock, nor did he do the commercial. He called up some pals and gabbed about the experience. Then he went about his business, proving his poor judgment with “hits” like America’s Sweethearts and Serendipity.

Good, John. Among the blunders in your track record, and there have been quite a few, this might go down as the worst.

What would you have done in his shoes? Think you would’ve been able to spot the potential of these Apple products as far back as 10 years ago?

[via GeekSugar]