The best woeful, weird, and wonderful Microsoft commercials of the past decade

Surface ad
Surface ad (Image credit: Microsoft)

Microsoft hasn't always been the best when it comes to marketing. Those aggressive Windows Phone ads of yesteryear didn't exactly pan out as hoped, and the first Surface commercial was just plain ... weird. However, we got some real tear-jerkers from Microsoft as well, as it highlighted the need for greater accessibility technology, while also finding its footing in some slick and sexy advertisements for its Surface lineup.

I thought it might be fun to cast the spotlight back, and look at some of the commercials Microsoft has put together over the years. From the cringe to the plain cool.

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Microsoft Kin ad (2010)

This horrifyingly bad Microsoft Kin ad from 2010 showcases pretty much everything that was wrong about Microsoft's marketing efforts from the time. We get a bunch of flashy images that explain basically nothing about what the product does, hoping that "coolness" will win the day. Kin was a spectacular failure, shocker!

Madobe Nanami Windows 7 anime ad (2010)

Back in the early 2010s, Microsoft Japan actually produced a range of anime-themed ads based on the OS-tan meme, personifying various operating systems as kawaii anime girls. This one from 2010 shows off some of Windows 7's features, including early touch support.

Nokia Lumia 800 ad (2011)

I'm cheating slightly with this, since it's a Nokia ad, not a Microsoft ad. Still, this fun piece showcased the best of what Microsoft was trying to do with the Windows Phone operating system, without all the artsy over-thinking of some of Microsoft's own later ads.

Microsoft "Productivity" (2011)

This isn't exactly a commercial, but it deserves a shoutout nonetheless. This futuristic vision reel showcases some of Microsoft's aspirations for the future of tech and productivity. Most of it probably won't come to pass, but hey, it's fun to dream.

"Movement" Surface ad (2012)

While the trailer is slick and well-presented, arguably this was one of the worst ways to showcase a new product form factor. All sorts of dancing people jump around with Surface devices, asking the viewer to examine the subtext for information on why the Surface form factor makes sense. Future ads would be far better than this overthought piece of marketing.

"Everything at once" Windows 8 ad (2012)

Windows 8 was the OS that-never-was, kinda. As much as many of us liked what it was trying to do, it turns out that trying to upend decades of muscle memory training turned out to be unpopular.

Internet Explorer 11-tan anime ad (2013)

Again with the anime, Microsoft also tried to showcase Internet Explorer 11 through the medium in 2013. If only the browser was as cool as the trailer.

"Don't fight" Windows Phone ad (2013)

This was a good one. Microsoft's Windows Phone 8 ad took direct aim at the iPhone and Galaxy phones du jour, all the way back in the early 2010s. The ad mocks Apple and Samsung, positioning the Lumia 920 as a colorful alternative. We loved you Lumia, we really did.

iPad vs. Windows 8 (2013)

Microsoft created a range of ads highlighting Windows 8 as an alternative to the iPad, showcasing products like the old Dell Venue 8 Pro, as a cheaper, more capable Windows option. Windows would end lagging far behind iPad in the "tablet" form factor wars, with few apps that support touch ergonomically, but Apple "borrowed" many features Windows 8 and Surface pioneered in the years that followed.

Xbox One reveal (2013)

Watching this trailer back now as we head into 2020 is a bit cringe. Almost every feature showcased in this trailer has since been stripped out of the Xbox One, or simply never came to pass. Kinect's camera reticle, ominously filling up the screen — discontinued. "Live TV" is being sidelined in favor of on-demand entertainment apps. Skype on your Xbox — who the hell asked for that? This was perhaps the worst console reveal in history, and it all leads back to this abysmal, uninspiring trailer.

Surface Book reveal (2015)

I feel like Microsoft really began hitting its stride with Surface reveals with the original Surface Book. The moment the display snapped off the base was a true jaw-dropper, complete with music that is almost reminiscent of some sort of Olympian triumph.

"Pure Imagination" Surface Studio reveal (2016)

The Surface Studio reveal ad might be among the sexiest tech showcases of all time, complete with an incredible and inspiring rendition of "Pure Imagination" from the 70s Charlie and the Chocolate Factory movie.

"Minecraft Super Duper Musical" (2017)

Here's a fun ad that Microsoft probably hopes Xbox fans will forget (but sorry, I won't let you). Microsoft made a huge song and dance (literally) about the Super Duper Graphics Pack for Minecraft, which would modernize the game with new shaders and effects. Sadly, the Super Duper Graphics Pack was killed off, never to see the ray-traced light of day.

Surface Duo reveal (2019)

Purely for the true "WTF" factor, Microsoft stunned the tech press with this slick demonstration of the Surface Duo's capabilities. The mythical Surface Phone made flesh, running Android, no less.

"Mac Book says" Surface ad (2019)

Another recent one, Microsoft very sneakily found a way to perform a direct comparison between the Surface Laptop 2 and Apple Mac Book by finding a dude called Mackenzie "Mac" Book to slate Apple's laptop for a good 30 seconds. Good stuff.

Lucy and the Reindeer Holiday ad (2019)

Microsoft has produced a bunch of fun Christmas commercials in recent years. This one from 2019 is worth a look if you haven't seen it already, showcasing some of the features of the Surface Pro X and Bing Translate.

"We All Win" Microsoft Superbowl ad (2019)

Microsoft made millions cry when it used its Superbowl ad space to highlight gamers with disabilities this year. Microsoft's aggressive investments in accessibility features is one of the best things (if not the best) thing to have happened at the company in recent years, and this trailer highlights why it's so important.

Do you have a favorite?

What was your favorite Microsofty ad of the past decade? What are we missing here? Hit the comments, let us know. And finally, Happy New Year!

Jez Corden
Co-Managing Editor

Jez Corden is a Managing Editor at Windows Central, focusing primarily on all things Xbox and gaming. Jez is known for breaking exclusive news and analysis as relates to the Microsoft ecosystem while being powered by tea. Follow on Twitter @JezCorden and listen to his XB2 Podcast, all about, you guessed it, Xbox!