10 Questions for Cortana, Siri, Amazon Echo and Google Now

Microsoft’s Cortana virtual assistant is making its desktop debut with Windows 10. How does it compare against the competition?

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Which virtual assistant gives the best answers?

After its out-of-town tryout on Windows Phone 8.1, Microsoft’s Cortana is hitting the big stage with today’s release of Windows 10 (though the virtual assistant won’t be available in all markets.)

So I fired off roughly 25 questions and commands (some silly, some not) to Cortana, Apple’s Siri, Amazon’s Echo and Google Now. The following 10 responses showed off their differences the most. In my highly subjective tests, Siri triumphed, getting my winning vote for five of the 10 responses—but also providing some really disappointing answers, too. Echo and Google Now tied for second place, receiving three votes each; Cortana ranked last, with two votes. Maybe Cortana still needs a little more out-of-town fine-tuning?

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“Tell me a dirty joke.”

Did any of the virtual assistants “go there” and deliver a raunchy joke? Not even close. Instead, not surprisingly, they went for clean, corny and safe. Siri’s response was sort of tired: “Too clods walk into a bar … No, definitely too silly.” Google Now simply supplied a list of Google search results for joke sites. Cortana’s joke wasn’t in any way “dirty” but was mildly amusing: “What did the passive-aggressive raven say? ’Nevermind. Nevermind.’” Echo’s response was the best, but compared to the competition, that’s not saying much: “Want to hear a dirty joke? A boy fell in some mud. How about a clean joke? He had a shower.”

Winner: Echo

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“What’s the meaning of life?”

Can a virtual assistant answer the greatest question of all time? Yes, if you’re a Douglas Adams fan. Adams authored “The Hitchhiker’s Guide to the Galaxy,” a series of popular books, stage plays and so on. In “Galaxy,” a supercomputer spends 7.5 million years computing the answer to the “ultimate question of life, the universe and everything.” Its answer: “42,” though “the answer seems meaningless because the beings who instructed it never actually knew what the Question was” (Wikipedia). Echo got the pop cultural reference, answering simply “42.” So did Cortana: “I’ve heard from a reliable source that the Answer is 42,” it replied, then added, “But still no word on what the question is.” Siri’s response: Chocolate.

Winner: Cortana

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“How do you say ‘I’d like a glass of white wine’ in Italian?”

Some might argue that wine is the meaning of life, and therefore it’s essential to know how to order it when traveling internationally. Echo couldn’t answer this question at all. Siri and Cortana just gave me some Bing search results, which weren’t helpful, as they listed links to sites that would tell me about ordering white wine in French or red wine in French or Italian—but not white wine in Italian. Google Now rocked this one, not only showing me the answer but speaking it in Italian, too. Molto bene, mille grazie!

Winner: Google Now

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“When is my next SoulCycle appointment?”

A friend coerced me into taking SoulCycle classes with her (for the record, they’re a bit cult-like but definitely a good workout). So I asked each of the virtual assistants to check my calendar for my next SoulCycle session. Echo could only tell me what my next two calendar appointments were. It took Siri five tries to figure it out — I had to change “SoulCycle” to “Soul Cycle” in my calendar before it could identify that appointment on my calendar. Only Google Now and Cortana came through.

Winner (Tie): Cortana and Google Now

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“How many games have the Boston Red Sox won this season?”

Cortana and Google Now didn’t answer the question directly. Instead, they just threw some Web search results at me. Echo said it couldn’t “find the answer to the question I heard.” Only Siri knocked it out of the ballpark, letting me know that (as of the moment I asked) the Red Sox were “42-54” and showing me where the team currently ranks in its division.

Winner: Siri

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“What’s the worst movie Meryl Streep ever made?”

Even the often-praised, ridiculously talented Meryl Streep must have a bad day at the office now and then. So which of her movies should we really, really avoid? Echo simply said it couldn’t find the answer to my question. Google Now and Cortana demurred, showing me search result listings that I’d need to dig through to find the answer. Siri came the closest to providing a direct answer by displaying Streep films in order of their Rotten Tomatoes scores, starting with the lowest. The answer: It’s a tie between “Lions for Lambs” and “Evening.”

Winner: Siri

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“Show me a funny cat video.”

Wouldn’t it be cool if you could just issue this command and boom, your device begins showing a hilarious kitty cat video? It didn’t quite work out that way for me, probably because humor is subjective and the virtual assistants want you to choose for yourself. At any rate, I gave Siri the nod here. Unlike its competitors, Siri displayed a page of thumbnail videos (though without description). The video displayed at the top left was a 10-minute compilation of various funny cat clips, including one in which a kitty unfurls a toilet roll.

Winner: Siri

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“How do you spell ‘discombobulated’?”

Granted, this question isn’t on everyone’s lips. But many of us need a little spelling help now and then, and discombobulated is one of my favorite words, so why not see how the four contenders might help me out? Cortana was the least helpful, feeding me Bing search results that showed me how to spell the word (plus a Yahoo Answers result that defined the word). Siri, Google Now and Echo each took the extra step and spelled out the word audibly, too.

Winner (Three-Way Tie): Siri, Google Now, Echo

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“What’s the best phone?”

Admittedly, this is like asking a San Francisco Giants fan, clad in Giants baseball cap and T-shirt and cheering loudly for the team at a home game, which is the best baseball team? I could pretty much predict what the virtual assistants would say in their answers. What made me curious was how they would answer the question. Cortana said “I can’t pretend to be impartial” and showed a Windows Phone icon beneath the answer. Echo’s response: “The Amazon Fire phone of course!” (Glad somebody thinks so.) Google Now was impartial, feeding me a list of search results that started with an article on the ’10 best smartphones in the U.S.’ I liked Siri’s answer best: “Wait … there are other phones?”

Winner: Siri

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“Why did the chicken cross the road?”

This question has baffled the world’s leading scientists and philosophers even more than that vexing “meaning of life” business. In my search of a conclusive answer as to the chicken’s street-traversing motivation, Cortana’s response was “Oh, did she? I hadn’t heard.” (Meh.) Google Now, as is its wont, gave me Google search results that included a Wikipedia article devoted to the riddle. Siri’s answer was yawn inducing. First, it was: “Sorry, too easy.” I asked again, only to be told, “I don’t understand why people ask questions they already know the answer to.” (Um, because they want you to be clever?) Echo stole the show by telling me it’s “really only the chicken’s business.”

Winner: Echo