Top 9 Worst Microsoft Ads Of All Time

7.”Financial Planner”

Wes Moss: certified financial planner, genuine douche. But what’s worst about this ad isn’t its slimy spokesman. It’s the specious logic that actually works to undermine all the things that were so great about Zune when it first launched.

8.Kin Hipsters

This Kin spot caught a lot of flack for containing “sexting,” but the guy taking a pic of his chest doesn’t bother us nearly as much as the sad, aggressive hipster courting that went on with Microsoft’s whole Kin campaign.