--Jim Allchin, Microsoft
The idiom "lipstick on a pig" was probably made more popular during the 2008 US elections because of a certain "phony" argument. But either way, we have written quite extensively about Windows Mobile and predictions of its doom, e.g. here. As rumours about a Microsoft phone started to swirl (Microsoft seems to be denying it, labeling this mythical phone "phony"), GigaOM, the site owned by a temporary Microsoft Munchkin, once again took a shot at it, saying it would be like "lipstick on a pig."
When I read an Inquirer piece about Microsoft launching its own branded phone with a Tegra chipset by Nvidia, it struck me that this would truly be putting lipstick on a pig.
As someone who has been following Microsoft for over 25 years, I remain staggered by the completeness of the Vista fiasco. Microsoft's constant backtracking on the phasing out of Windows XP is perhaps the most evident proof of the fact that people do not want to be forced to “upgrade” to something that has been memorably described as DRM masquerading as an operating system.