How Apple Lost Its Cool (And How It Can Get It Back)

September 3, 2026

Timothy Beck Werth asking the question

When was the last time you saw a truly unforgettable Apple ad?

Steve Jobs built Apple into an empire by making advertising history, turning laptops and MP3 players into status symbols. But on the eve of another iPhone launch, it’s been a decade since Apple made a classic commercial. In fact, the biggest ad of the Tim Cook era was 2024’s tone-deaf 'Crush' ad, which people hated.

So, how did Apple go from rebellious tech underdog to exactly the type of bloated corporate monopoly it used to mock? It turns out, you can chart 40 years of Apple history through just seven commercials. Here is how Apple lost its cool factor—and how they can get it back.

Apple's Sunrise and Shine Event will be live on 9/9 at 1pm EST / 10am PST.

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