By many accounts, Steve Jobs the CEO was a formidable, occasionally intense presence in person, but he can't be accused of being humorless. When he first met Steve Wozniak as a high school student in the early '70s, they reportedly bonded over tales of grand pranks they'd pulled. Another such prank would come decades later, when Jobs famously called a local Starbucks while on stage introducing the iPhone and ordered 4,000 lates. "No just kidding, wrong number," he told a bewildered employee. 

Later as the pressure piled on at Apple, Steve would use humor to diffuse whatever tension was in the air, like when he triggered a slide with the famous Mark Twain quote "Reports of my death have been greatly exaggerated," after he underwent chemo for pancreatic cancer; or when he told an audience to "Stop me if you've seen any of this before" while unveiling the iPhone 4 in the wake of Gizmodo's infamous leak earlier that year.