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The worst Microsoft celebrity videos ever

With the news that Will Smith appears in a new video singing a song about Windows 7, we went in search of the worst Microsoft celebrity video howlers

Richard Trenholm Former Movie and TV Senior Editor
Richard Trenholm was CNET's film and TV editor, covering the big screen, small screen and streaming. A member of the Film Critic's Circle, he's covered technology and culture from London's tech scene to Europe's refugee camps to the Sundance film festival.
Expertise Films, TV, Movies, Television, Technology
Richard Trenholm
3 min read

Microsoft has a history of terrible videos -- here are our favourite promo howlers -- but nothing trumps the attraction of Microsoft's deep coffers. Hence the plethora of celebrity shills willing to attach their names to the brand's latest poorly written, clunkily shot videos, including such cultural icons as David Brent, Superman and Dolly Parton.

Recently, we heard Will Smith had taken the M$, only to discover it was a suited and booted ankle-biter and not the famous chap. Standing on a fake stage at a made-up talent show contest, which is made-up and also fake, pint-size Smith sings a song called Windows 7 Rising to the tune of Bad Moon Rising by Creedence Clearwater Revival. It's awful. Now here's some genuinely famous people being paid by Microsoft to sprinkle some Hollywood cool on whatever they were selling that year -- and failing miserably.

What is the deal with Windows: Jerry Seinfeld

As Bill Gates prepared to bow out of Microsoft, he teamed up with Jerry Seinfeld for this odd little ad.

Microsoft Office: Ricky Gervais and Stephen Merchant

Ricky Gervais reprised the role of David Brent from The Office alongside writing partner Stephen Merchant in these training videos discussing the brand values of Microsoft, whose UK HQ is in Gervais' home town of Reading. The videos were intended for internal use only, but soon leaked out. In total they're 20 minutes long -- you don't have to watch them all, we haven't.

If you're really keen, here's parts two and three. If you've had enough Microsoft brand values, skip straight to 4:47 for the outtakes.

Saved By The Surface: Mario Lopez

If watching vapid celebrities coo over pictures of themselves is your idea of entertainment, have we got the video for you! Slater off Saved By The Bell presents a show called Extra in which he and aforementioned vapid celebs play with a Microsoft Surface.

I'll be there for UI: Matthew Perry and Jennifer Aniston

Another training video, this time featuring Matthew Perry and Jennifer Aniston. Perry gives it his all while Jen just looks bored, perhaps wondering when Brad Pitt will take her away from all this. Terrible writing is par for the course, but it's the musical stings that make it art.

Super 8: Dean Cain

Midway through this year Microsoft launched this bizarre series of spoof promos for Internet Explorer 8, fronted by ex-Superman Dean Cain and directed by ex-Police Academy gurner Bobcat Goldthwait. This one involves SHYNESS (Sharing Heavily Yet Not Enough Sharing Still).

The video that made headlines was this one. If you didn't see it at the time, we warn you: it's called OMGIGP (Oh My God I'm Gonna Puke) and it's really not very nice...

IE8 in actually quite good shocker: Janeane Garofalo

Here's another Internet Explorer 8 video starring Janeane Garofalo, Ask A Ninja and some people you've never heard of it. Hang on -- this is actually, whisper it, quite good.

IE 8 for the 9 to 5: Dolly Parton

One of the new features of Internet Explorer 8 is Webslices. Who better to explain than Dolly Parton? Probably quite a few people, actually. Take it away, Dolly.

We meant take Internet Explorer 8 away, but whatever.