From Harry Potter to Darth Vader: When CEOs play dress up

Steve Ballmer – Microsoft

While talking with TV host Conan O’Brien, former Microsoft CEO Ballmer was praised for doing his part to bring renewed energy and a sense of fun to the leadership role in a number of parodies. In the show, O’Brien hailed a comedy sketch of Austin Powers as being genius, in which Ballmer managed to get Gates to play a part as well.

For your viewing pleasure, here are two more sketches Ballmer took part in: from Night at the Roxbury to The Matrix.

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Steve Jobs – Apple

Not to be outdone, Apple CEOs have also been known to dabble in the art of dress up. Take, for example, Steve Jobs, who in 1984 released a spoof of Ghostbusters where he impersonated FDR. At the time, Jobs and his team of “Bluebusters” were trying to challenge IBM, with the video being produced by Apple to open a worldwide sales staff meeting in Hawaii.

Also shown at the meeting was another video starring Jobs as president Franklin Roosevelt.

He’s also reportidly dressed up as Jesus. And during a summer college break, he and Steve Wozniak were paid $3 an hour to dress up as the White Rabbit and Mad Hatter from Alice in Wonderland to entertain children outside Westgate Mall in California.

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Warren Buffet – Berkshire Hathaway

In 2010 Warren Buffett showed the world a whole new side of himself by donning a purple bandana, an Axl Rose wig and fake tattoos to belt out a rock ballad for staff at his insurance company, Geico.

In a promotional video that rapidly went viral, he joined employees in a somewhat cheesy number called “All for You”‚ which was supposed to trumpet the importance of customer service.

Warren Buffet and Jay-Z have attributed their success in the business world to luck

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Richard Branson – Virgin

Out of any CEO that’s reigned supreme, Branson has the biggest reputation for playing dress up! And let’s face it, he’s pretty much dressed up everything under the sun. 

He wrote in a blog post, “I love playing dress up, and over the years have found it to be a great way to attract attention to the Virgin message.” 

When it came to his stint as stewardess, however, Branson got dressed up as a female after honouring a bet he lost to Air Asia’s CEO Tony Fernandes in terms of who would win the 2010 Formula 1 Grand Prix.

The list of costumes could have taken an entire article of its own. But a few of his projects deserve mentions, having seen him pose as the Easter Bunny, Santa Claus, a pirate, a boxing champion, a butterfly and a rail station bin man complete with sleeve tattoos, blackened teeth and greasy hair.

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