Mr. IT

Microsoft was having a rough time around 2007. Jim Allchin, who ran Vista development, admitted in an interview that he’d buy a Mac if he didn’t work at the company. The company was stealing UI elements from competitors and pasting them onto their own websites. Bill Gates kept hearing from bloggers about how many of them used Macs. Everything pointed to trouble ahead.

So Microsoft did what Microsoft does: they came up with something so aggressively weird that you had to look. With HP, they created Mr. IT—a character, a mascot, a man with blonde hair and a perpetually friendly demeanor who wandered through offices in business casual, flirting with receptionists and having way too much fun with the copy machine. I didn’t want to know what came next in those spots. The whole thing was like watching someone throw a party to convince you they’re cool right before they realize nobody’s coming.

And somehow it worked, or at least it worked on me. I hated Microsoft then the way you hate someone you can’t quite quit. They were corporate, tone-deaf, always three steps behind where the industry actually was. Vista was a disaster. Every decision they made looked like it was designed by a committee that had never seen a computer before. But they had this weird confidence. They could spend millions on a campaign that was objectively ridiculous and somehow make you remember it, make you think about it.

I still hate them. But they got me. They always get me. There’s something weirdly beautiful about that kind of failure disguised as ambition.