Gates said he'd pull up a slideshow of photos with a single click on the remote control. But he clicked ... and clicked ... and nothing happened. The audience gasped and roared with laughter.
"Right now nine people are being fired," O'Brien said as Gates fumbled with the remote. "Digitally fired!"
Gates changed the subject and O'Brien tried to keep it light. But they attempted the slideshow again, and it failed -- two more times.
"And again...just incredible," O'Brien murmured. "I don't know who's running things here. Who's in charge of Microso-- Oh."
The demo hell wasn't over. Later in the presentation, Microsoft program manager Garrett Young tried to spotlight personalization options for a racecar in a video game. As Young showed off paint jobs and decals, a system failure caused the infamous "Blue Screen of Death" to pop up.
"I'm sorry, I'm out of system memory, apparently," Young said, hastily shutting down the program. "So just imagine, if you will, that I was customizing my car."
NEXT: 2009: Palm Pre
