This Guy Rappelled Down the CN Tower For the Launch of Windows 95

Twenty years ago this week, Microsoft released Windows 95 to the world.

It might be hard to imagine now, but the launch of a new operating system was a huge deal back in 1995. When Windows 95 launched, there were parties at midnight where people lined up at stores around the block. Microsoft ran lengthy ad spots on TV and spent about $3 million to license the song "Start Me Up" by the Rolling Stones. They lit the Empire State Building up red, yellow, and green, the colours of Microsoft's logo, and even unfurled a massive, 300-foot banner down the side of the CN tower in Toronto.

Microsoft spent a reported $300 million on marketing alone.

But the coolest stunt was easily conducted by Canadian rappeler and Guinness World Record holder Stuart Leggett. Leggett was hired by Microsoft's PR team to rappel down the side of the CN Tower while using a laptop running Windows 95—and a few hundred feet into his descent, he would send an email, wirelessly, to then-Microsoft CEO Bill Gates.

"At the base of the tower they had a bunch of tents set up, and the public could come in there and try the new program," Leggett told me when I reached him via phone. "There were computers everywhere. The big Microsoft banner was hanging down the side of the tower. They had a big light show. They had all kinds of things going on, culminating with the stunt."

The idea, Leggett was told, was to capture the excitement of ad spots featuring the Rolling Stones song that Microsoft had licensed. The plan was to have Leggett descend from the CN Tower's space deck—known today as the SkyPod, which stands 1,465 feet above the ground—and land on a giant Start Button lying below. (The whole tower is 1,815 feet, 5 inches, by the way.)

Leggett would have a laptop connected to his harness running Windows 95, with an early, internet-connected Nokia phone strapped to his belt (remember, this was extremely cutting edge for the time). From the space deck, he would descend to the roof of the tower's revolving restaurant where waiting journalists would watch him initiate a network connection and send an email to Bill Gates, who would receive the email during the Windows 95 launch event on stage (the email was mostly written by Microsoft PR ahead of time, but Leggett got to add some flourishes of his own during the descent).

"What they told me is, 'When you send this email, that will queue the Rolling Stones," Leggett recalled. "They didn't really think that it was possible," he later added.

The whole thing was meant to show how easy it was to use Windows 95—so easy, in fact, that you could even use the operating system while hanging over 1,000 feet above the ground.

Of course, not everything went according to plan. Recognizing that it might be difficult for Leggett to rappel, compute, and speak with the press at the same time, Microsoft's PR team planned to setup an automated script ahead of time that would automatically perform all of the tasks that Microsoft wanted Leggett to perform. But before the rappel was set to begin, they realized the script hadn't been installed, Leggett recalled.

Microsoft's PR reps tried to give Leggett a crash course as best as they could in those few minutes before his descent. In the end, a journalist on the roof who was familiar with the software taught Leggett how to perform the tasks he needed to do on queue. After that, the whole thing went off without a hitch.

The stunt was actually Leggett's fourth time scaling and rappelling down the CN Tower. He first climbed and then rappelled down the CN Tower in 1985, followed by a climb in 1986 that ended with a mock rescue demonstration (people were rescued down a rope that terminated a few blocks away from the tower, on Bathurst street, for those familiar with the city). Leggett called the two events and others like it "lifeline" events, which were meant to raise awareness of alternate forms of rescue from tall buildings and structures via rope.

Another climb and rappel was done in 1992 for Canada's 125th anniversary celebrations with a group of British Royal Marines, followed by the Windows 95 stunt.

Nowadays, Leggett works as an artist with his wife in Midland, Ontario, creating sculpted paintings, but is still regularly contacted by people seeking advice on challenging climbs, descents and planning rescue scenarios. He's still waiting for that email back from Bill Gates.