As “Cortana” Approaches, Remembering Microsoft’s Other Digital Assistant: Ms. Dewey


Microsoft is apparently readying its own digital assistant called “Cortana,” to take on Apple’s Siri and Google Now. Hopefully, Cortana will see more love than Microsoft’s other assistant that you have probably long forgotten about. Ms. Dewey.

Ms. Dewey? She was an experimental interface launched in October 2006 for Microsoft’s search engine Live Search (now called Bing). Actually, she was more an underground marketing campaign. She gained buzz because she was an assistant with attitude, if she had issues with what you searched for. Howard Stern? As this Marketplace report from the time covered, she’d respond with:

 I just got satellite radio so I could hear what’s his face swear. Know what? I don’t see what the big f**kin’ deal is.

You can entertain yourself for ages going through the videos still out there in a search for Ms. Dewey on YouTube, but I enjoyed this Ms. Dewey’s Greatest Hits clip over on Vimeo:

And yes, Ms. Dewey really would give you results, if you put in a search she didn’t have a canned snappy answer to. Below is an example for a search on “who won the elections today,” which brought up clickable search results next to her:

Alas, Ms. Dewey went the way of Microsoft Bob and Clippy. The domain of her site,, was allowed to expire, along with the concept. Actress Janina Gavankar, who played her, has gone on to a variety of roles in shows like True Blood and Arrow.

As for Cortana, Microsoft’s expected digital assistant to come perhaps in April, the name seems to come from a character in the game Halo. Here’s your essential background on that:

However, only the Cortana name — not the character — will be used. Here’s a video of the tool that’s leaked out:

Unlike Ms. Dewey, Cortana looks to be far more useful. You can read more in Unleash The Phones, which got the leaked video, and in our summary on Search Engine Land: New Video Shows Microsoft “Assistant” Cortana In Action.

Related Topics: Apple: Siri | Channel: Mobile Marketing | Google: Google Now | Microsoft: Cortana | Microsoft: Windows Phone


About The Author: is Founding Editor of Marketing Land. He’s a widely cited authority on search marketing and internet marketing issues, who has covered the space since 1996. Danny also serves as Chief Content Officer for Third Door Media, which publishes Search Engine Land and produces the SMX: Search Marketing Expo conference series. He has a personal blog called Daggle (and keeps his disclosures page there). He can be found on Facebook, Google + and microblogs on Twitter as @dannysullivan.

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  • Ric Dragon

    I LOVED Ms Dewey! I was heartbroken that they discontinued.

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